The Best Airbnb & VRBO Vacation Rentals in the Berkshires (June 2021)

Cabin Rentals and Family-Friendly Vacation Homes in Stockbridge, Lenox, Great Barrington, Williamstown, & More
Family trips to the Berkshires are a quintessential part of life in Massachusetts. The area offers a beautiful backdrop for a family vacation, with AirBnB cabin rentals giving groups of all sizes the opportunity to experience the best of the Berkshires.

The historic small towns of Western Massachusetts, such as Stockbridge, Williamstown, and Lenox have many beautiful mountain homes that let visitors enjoy the best of the Berkshires - from hiking to festivals and farm to table restaurants, Berkshire County has it all.

For families who want to make the most of their visit, an Airbnb or VRBO vacation rental is the best option. Many rental houses and cabins offer relaxing outdoor spaces with fire pits, hammocks, and some even have pools.

Below are several of the best vacation rental houses in the Berkshires.

Jump to: Lenox | Stockbridge | Pittsfield | Great Barrington | Williamstown | Lee | North Adams

Lenox Airbnb's and VRBO's

Lenox is a favorite destination for visitors to the Berkshires. It's a small town set against the backdrop of the beautiful southern part of the Berkshires. It has a lovely downtown area that's perfect for walking. The historic New England architecture gives this hamlet a sense of character. There are a number of great local restaurants, as well as health spas and art venues. The town is also famous for its Tanglewood Music Festival, which features the Boston Symphony Orchestra.

Kids will love the hiking trails in the area. There are many trails that feature rolling hills and aren't too strenuous for little legs. Horse lovers will enjoy a trail ride, which is the perfect way to experience the Berkshires.

This town has a number of excellent vacation rentals for families. Below are some of our favorites in and around Lenox.

"Village View"

Lenox, Massachusetts
The list goes on and on with this beautiful house in Lenox, so add this one to your list of favorites. The location of this vacation rental is perfect as it's right in Lenox. This place is just a few minutes away from Zinc and Haven. If you just want to eat in, the fully-equipped kitchen will let you cook all of your meals. Everyone can spread out in the living room, dining room, and porch, too. With space for the whole group, this is a great vacation rental for the entire family. Each bedroom offers a comfortable place to relax. One bedroom has a king-sized bed and several other rooms have queen beds. Board games, a grill, and parking are also on the list of amenities. Check out the photos!



Heart of Lenox, Walk to Town

Lenox, Massachusetts
With room for 4 people, this is a 2-bedroom house that makes for a perfect Lenox vacation rental in the Berkshires. It's located perfectly in Lenox so you can explore town on foot, or easily drive to the other nearby towns. As for the interior, this house has all of the comforts you need. The microwave and dishwasher in the full kitchen will let you cook all of your meals if you like. Each bedroom offers a comfortable place to relax. Each has its own king-sized bed, which is perfect for couples traveling together. And with the living room, dining area, and porch, everyone will be able to spread out and relax. Smaller families and couples love this spot, as it's just the right size and price.



Lenox Lake House in the Berkshires

Berkshire County, Massachusetts
This lakefront house is a great place to base yourself during your time in the Berkshires. Relax by the water before heading out to eat and shop local in the nearby boutiques and cafes.. Featuring 4 bedrooms and 2 bathrooms, there's plenty of room for up to 10 people here, so add it to your wish list. This large house is perfect for a big family or group of friends. Enjoy cooking your meals in the kitchen, which has modern appliances including a microwave, oven, refrigerator, and dishwasher. There's also the dining area offering more space to guests. The 4 bedrooms are nicely laid out so everyone can sleep comfortably. With a king-sized bed in the master, plus queen beds in other bedrooms, everyone will be comfortable. Other amenities include parking, a garage, and a grill. Staying here will make your trip to Berkshire County fun and convenient. Are you ready for a fun lake house vacation? This is the spot!



Cozy Berkshires Cabin

Stockbridge, Massachusetts
This cabin is a popular option because it's by the lake. It has 2 bedrooms and 2 bathrooms. This cabin is perfect for a large family or friends group. Both bedrooms are nicely furnished. There's a king-sized bed in one bedroom and a queen in the other. The kitchen is convenient, well stocked, and of course has everything you need to cook all of your own meals. You will also find a grill, parking, and internet at this vacation rental. Of course, the main attraction here is the lake, and you'll have a blast around the water and relax admiring the gorgeous views.



The Playhouse

Berkshire County, Massachusetts
This is a huge 6-bedroom, 5-bathroom place that is spacious and beautiful. It can accommodate up to 20 guests. This large property is perfect for group events, family reunions, and larger gatherings. The 6 bedrooms are nicely laid out so everyone can sleep comfortably. And with multiple rooms with queen beds, everyone will have their own space. The fully equipped kitchen has everything you need such as a microwave, dishwasher, stove, and oven. The huge open layout of this house means that everyone can have fun while still being part of all of the activities (and you can keep an eye on the kids).

The hosts clearly work hard to make visitors happy, because this rental has earned a terrific rating with plenty of positive reviews. Tanglewood Music Center, Norman Rockwell Museum, National Shrine of the Divine Mercy, Lee Prime Outlets, Salmon Run Fish House, and Chez Nous are within five miles of this place. It's hard to find a place like this, so check it out before it's booked up.



Renovated 3-Bedroom in Lenox

Lenox, Massachusetts
For anyone that wants a fun-filled vacation in Lenox, this 3-bedroom, 2-bathroom house is a great vacation rental as it can accommodate 6 guests. With space for the whole group plus a huge yard, this is a great vacation rental for the entire family. The fully equipped kitchen has everything you need such as a microwave, dishwasher, stove, and oven. All of the bedrooms are nicely furnished. There's a king-sized bed in the master bedroom. There's also the living room and dining area offering more space to guests. And you'll love relaxing on the back patio with the outdoor seating area while the kids play in the yard. A grill, parking, and internet are also on the list of amenities. You'll find many quaint shops in the area. This is a great spot to enjoy your next trip to Lenox and the Berkshires.



Downtown Lenox Home

Lenox, Massachusetts
Meet the friendly locals and enjoy the small town charm at this beautiful house. This Lenox house has a number of comfortable touches and a relaxing atmosphere. The 3-bedroom, 1-bathroom vacation rental has a nice long list of features and has room for up to 6 people. There's plenty of space here for the whole family or group to hang out. All of the bedrooms are nicely furnished. You can either go out to eat or just stay in and cook all of your meals in the kitchen. You'll also be able to spread out through the porch.

Other amenities include parking, internet, and a garage. This is a comfortable option for anyone headed to Lenox. You'll also find Tanglewood Music Center and Cranwell Golf Club less than 3 miles away.



Staycation at Chic Comfortable Contemporary Home

Lenox, Massachusetts
Places like this get booked up quickly. This 3-bedroom house can fit up to 8 people. This house is perfect for a large family or friends group looking to explore the Berkshires. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. Two of the bedrooms have queen-sized beds. Guests enjoy the full kitchen which is great for preparing home cooked meals. The living room, which offers even more space to relax, will make you feel right at home. Also on the list for this house is parking and internet. Add this one to your wish list!



Very private setting, yet walk to town

Lenox, Massachusetts
If you're looking for a vacation rental in Lenox, this 3-bedroom, 1-bathroom house is a great option. This amazing house has everything you need, and provides it all with style, too. There's plenty of space here for the whole family or group to hang out. All of the bedrooms offer everything that guests could need. Two of the bedrooms have queen sized beds, which is great for everyone. Not too far away you'll find Tanglewood Music Center and Norman Rockwell Museum.



Heart of Lenox

Lenox, Massachusetts
Relax in a small town setting here. A popular vacation rental in Lenox is this roomy 2-bedroom, 1-bathroom apartment that has room for up to 6 people. This is a great option for a family as there's room for everyone. Check out the photos! The kitchen is well stocked with a refrigerator and dishwasher. Both bedrooms offer everything that guests could need. There's a king-sized bed in one bedroom and a queen in the other.



Modern, Comfortable Classic House

Lenox, Massachusetts
Meet the friendly locals and enjoy the small town charm at this beautiful house located in Lenox. This is a large space and would be perfect for a big family, or multiple families on vacation together. The 4-bedroom, 2-bathroom house has a great location. Located less than five miles away you'll find Tanglewood Music Center, Lee Prime Outlets, Bousquet Ski Area, and Cranwell Golf Club. Places like this get booked up quickly.



Stockbridge Airbnb's & VRBO's

Stockbridge is another charming town in a central part of the Berkshires. The downtown is a bit smaller than Lenox and there are just a handful of restaurants to choose from, but there are nice trails along the Housatonic River. This town is known for its cultural sights. Make sure you check out the Berkshire Theater Group, which is popular for its plays and musicals. Kids and adults will also enjoy a visit to the Norman Rockwell Museum, where you can see a number of famous works. For food, a trip to Stockbridge isn't complete without a meal at the Lion's Den. They offer classic New England dishes that kids and adults will love.

There is also no shortage of outdoor activities near Stockbridge. Hiking and skiing are both popular in the area.

A number of large houses are available for rent near Stockbridge. These properties are often on vast acreage and have a sizeable amount of space for families to gather. Below are a few of our favorites.

Spectacular Setting on Private Lake

Berkshire County, Massachusetts
Wow! This gorgeous cottage house sits on its own private lake and has a number of comfortable touches and a relaxing atmosphere. The 4-bedroom, 3-bathroom vacation rental has a nice long list of features and has room for up to 10 people. This property would be an amazing option for a family or a group with all of its extra space. The 4 bedrooms are nicely laid out so everyone can sleep comfortably. There's a king-sized bed in one bedroom and a queen in another. Kids enjoy the bunk beds found in one of the bedrooms, too. The kitchen is well stocked with a microwave and dishwasher. The living room and dining area, which offers even more space to relax, will make you feel right at home.

Games, a grill, parking, internet, and a ping pong table are also included. This one is a good find for anyone headed to to the Berkshires. Feel free to bring your pets to this property, too. You'll also be very close to Tanglewood Music Center and Norman Rockwell Museum, as the location is convenient.



Modern Cottage in the Heart of the Berkshires

Stockbridge, Massachusetts
This roomy 3-bedroom, 1-bathroom house is amazing, and has room for up to 8 guests. If you're looking for comfort and convenience, this is a great house. Wake up in the morning with your coffee on the balcony, or unwind with a glass of wine in the evening. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends.

You can either go out to eat or just stay in and cook all of your meals in the kitchen. The living room and dining room, which offers even more space to relax, will make you feel right at home. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. There's a king-sized bed in one bedroom and a queen in another.

And more amenities are found here such as games, a grill, parking, internet, and a garage. Pets are welcome, too.



In-Town Victorian

Stockbridge, Massachusetts
This Victorian house is a popular option in Stockbridge, as it has 12 bedrooms and 6 bathrooms. Many people enjoy staying at this large space for family reunions or group gatherings. You'll find nice furnishings in the bedrooms. With two of the bedrooms having king-sized beds, everyone will be able to sleep comfortably. The bunk beds in the other bedroom are perfect for children. The full kitchen is well stocked and convenient, and features a microwave and dishwasher. Enjoy meals or relaxing in this property's living room, dining room, and porch.

Included with this property is games, a grill, parking, internet, and bicycles. As an added bonus, your pets are welcome, too.

Here you'll be situated in a great location close to Norman Rockwell Museum, National Shrine of the Divine Mercy, Once Upon a Table, and Main Street Cafe. This amazing house has everything you need, and provides it all with style, too.



Tranquil 3-Bedroom Stockbridge House

Stockbridge, Massachusetts
There's plenty of space here for the whole family or group to hang out. The 3-bedroom, 1-bathroom house has a great location. Tanglewood Music Center, Norman Rockwell Museum, and National Shrine of the Divine Mercy are also very close by. This one is a good find for anyone headed to Stockbridge. Cook all of your meals in the kitchen, as the microwave and oven are provided. You'll find nice furnishings in the bedrooms. The master bedroom has a king-sized bed. At this place, you'll also have parking, internet, and a garage.



Rabbit Run

Stockbridge, Massachusetts
A popular vacation rental in Stockbridge is this roomy 3-bedroom, 2-bathroom house that has room for up to 7 people. With space for the whole group, this is a great vacation rental for the entire family. This amazing house has everything you need, and provides it all with style, too.

For those who enjoy cooking, there's a full kitchen. There's even more space to hang out in the living room, dining room, and porch. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. There's a king-sized bed in one bedroom and a queen in another. Families and groups appreciate the game room. Fire pit, a grill, parking, and internet are also included. There's also golf and tennis in the area. As an added bonus for animal lovers, this property is pet-friendly as well.



"Too Good"

Stockbridge, Massachusetts
If you're looking for a vacation rental in Stockbridge, this 4-bedroom, 4-bathroom house is a great option. Staying here will make your trip to Stockbridge fun and convenient. With space for the whole group, this is a great vacation rental for the entire family. The 4 bedrooms are nicely laid out so everyone can sleep comfortably. With a king-sized bed in the master, plus queen beds in other bedrooms, everyone will be comfortable. Within just a few minutes you can get to Norman Rockwell Museum, National Shrine of the Divine Mercy, Once Upon a Table, and Main Street Cafe.



A Grand Estate in Historic Stockbridge

Stockbridge, Massachusetts
This gorgeous and historic house is a landmark in the area. It's large, beautiful, and luxurious. This 6-bedroom, 6-bathroom estate can fit up to 12 people. If you're planning a trip with a large family, you should definitely consider this stunning property.

All of the bedrooms offer everything that guests could need. Multiple bedrooms have king-sized beds, so everyone will sleep comfortably. You can either go out to eat or just stay in and cook all of your meals in the kitchen. There's also plenty of space in the living room, dining room, and porch as well. The place also includes games, a pool table, and a grill. Add this one to your must-see list!



General Williams Estate House

Stockbridge, Massachusetts
Guests love this historic property with multiple buildings, and it makes a great place to stay for your vacation in Stockbridge. The 6-bedroom, 5-bathroom vacation rental has room for 16 people. This place is just the right size for a large friends' group getaway. All of the bedrooms offer everything that guests could need. The master has a king-sized bed, and the extra bedrooms have queens. Guests enjoy the full kitchen which is great for preparing home cooked meals. Everyone can also relax in the living room and dining area.

The swimming pool at this house is not just fun, it's also private so you can relax in style. Everyone will enjoy this house's game room, too. You can take in the fresh air on the patio and enjoy some time to unwind. The house also includes games, a pool table, a grill, and parking. And the location is convenient to restaurants, shops, and activities nearby in the Berkshires, too.



Pittsfield Airbnb's & VRBO's

Pittsfield is the largest city in the Berkshires, but it still has plenty of charm and character. There is a lot for the entire family to enjoy. Pittsfield is known as the "city of festivals" and it really comes to life during the summer months when there always seems to be something going on. There's a city baseball team, a lot of parks, and plenty of activities for the family to enjoy. Kids will enjoy a visit to the Berkshire Museum, which has science exhibits, an aquarium, and even a large playroom. For the young and young at heart, a trip to Pittsfield isn't complete without a ride on the Berkshires Carousel (just $2).

One of the more popular destinations is the Herman Melville House, also called Arrowhead. Today it's a museum where you can learn about how this famous author of Moby Dick lived and worked. Theater lovers will also enjoy a visit to the Colonial Theater, which is part of the Berkshire Theater Group.

Because Pittsfield is larger than the other towns, many of the properties are a bit smaller. They're also more affordable than what you find in other towns in the Berkshires, so if you're looking for value at budget prices, then this is the place to stay.

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield, Massachusetts
For anyone that wants a fun-filled vacation in Pittsfield, this 4-bedroom, 4-bathroom lake house is a great vacation rental as it can accommodate 10 people. This property would be an amazing option for a large group with all of its extra space and plenty of fun activities on the lake. The full kitchen is well stocked and convenient, and features a microwave, oven, and refrigerator. You'll find nice furnishings in the bedrooms. One bedroom has a king-sized bed, while another has a queen. If you're traveling as a family, this is a great option because several of the bedrooms has bunk beds. And with the dining room, everyone will be able to spread out and relax. Parking, internet, fire pit, and a grill are also on the list of amenities.



Exquisite Apartment in Grand Victorian Home

Pittsfield, Massachusetts
This historic property is a nice and affordable apartment for a smaller family. The 2-bedroom, 1-bathroom apartment has a great location right in the middle of town. This amazing apartment has everything you need, and provides it all with style, too.

The kitchen in this apartment is very nice, and with a oven, refrigerator, and dishwasher you'll be able to cook for everyone. With a living room, dining room, and porch, there is enough space for guests to relax and hang out. Both bedrooms are nicely furnished. Both bedrooms have queen sized beds, which is great for everyone. At this place, you'll also have parking and internet.



4-Bedroom Lakefront

Richmond, Massachusetts
This renovated and modern lakefront house is a great place to base yourself during your time in the Berkshires. Featuring 4 bedrooms and 2 bathrooms, there's plenty of room for up to 8 guests here, so add it to your bucket list. This house is perfect for a large family or friends group. If you just want to eat in, the fully-equipped kitchen will let you cook all of your meals. And with the nice living room, dining room, and porch where you can spread out, this house will let you relax and unwind. All of the bedrooms offer everything that guests could need. You'll find two bedrooms with king-sized beds, and an extra bedroom has a queen.

And more amenities are found here such as games, a grill, fire pit, and parking. This is a great spot to enjoy your next trip to Richmond.



Spacious Berkshire Summer Rental, Private Dock on Lake

Richmond, Massachusetts
A popular vacation rental in the Berkshires is this roomy 3-bedroom, 1-bathroom house that has room for up to 7 people. It sits right on the lake and has a dock. Take a dip in the water or enjoy the views! This house is perfect for a large family or friends group. If you're looking for comfort and convenience, this is a great house. Within just a few minutes you can get to Tanglewood Music Center, Bousquet Ski Area, Hancock Shaker Village, and Berkshire Museum.

The kitchen is well stocked with a microwave, dishwasher, stove, and oven. There's also the living room, dining room, and porch offering more space to guests. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. Two of the bedrooms have queen-sized beds as well. Games, a grill, parking, internet, and beach chairs are also on the list of amenities. Pets are welcome, too.



Hidden Oasis in the Berkshire Mountains

Pittsfield, Massachusetts
This Pittsfield mountain view house has a number of comfortable touches and a relaxing atmosphere set in a gorgeous spot of land with stunning landscaping. The 5-bedroom vacation rental has a nice long list of features and has room for up to 10 people. This property would be an amazing option for a large group with all of its extra space. The 5 bedrooms are nicely laid out so everyone can sleep comfortably. With a king-sized bed in the master, plus queen beds in other bedrooms, everyone will be comfortable. The microwave, oven, and refrigerator in the full kitchen will let you cook all of your meals if you like. Enjoy meals or relaxing in this property's living room, dining room, and porch.

You will also find parking, internet, games, and a pool table at this vacation rental. Places like this get booked up quickly. Feel free to bring your pets to this property, too. With Tanglewood Music Center located just 5.2 miles away and Jiminy Peak Mountain Resort only 9.4 miles away, you'll find this to be a very convenient place to stay.



Huge Designer House

Berkshire County, Massachusetts
The list goes on and on with this large, modern, and gorgeous house in Berkshire County, so add this one to your list of favorites. The location of this vacation rental is perfect. Not too far away you'll find Tanglewood Music Center, Jiminy Peak Mountain Resort, Bousquet Ski Area, and Lee Prime Outlets. This house is perfect for a large family or friends group. You'll find nice furnishings in the bedrooms. The master has a king-sized bed, and an extra bedroom has a queen.



Berkshire Lakefront House

Berkshire County, Massachusetts
People love this house on the lake and it makes a great place to stay for your vacation in Berkshire County. The 2-bedroom, 1-bathroom vacation rental has room for 5 people. There's plenty of space here for the whole family or group to hang out. Each bedroom offers a comfortable place to relax. Staying here will make your trip to the lake fun and convenient. Within just a few minutes you can get to Jiminy Peak Mountain Resort, Berkshire Museum, Pittsfield State Forest, and Mount Greylock State Reservation Visitor Center.



A Beautiful Log Cabin In The Woods

Pittsfield, Massachusetts
This cabin on the lake is a popular option in Pittsfield, as it has 2 bedrooms and 1 bathroom. This cabin is perfect for a large family or friends group as it has plenty of space for everyone. The 2 bedrooms provide plenty of privacy. With a queen-sized bed, you'll sleep comfortably. The kitchen is convenient, well stocked, and of course has everything you need to cook all of your own meals. There's also the living room, dining area, and porch offering more space to guests. And you can walk right out to the water to enjoy the views or swim in the warmer months.



Great Barrington Airbnb's & VRBO's

Great Barrington has one of the larger downtowns in the Berkshires and there are plenty of restaurants, shops and activities to choose from. Kids will also love a visit to the Mahaiwe Theater. For a kid friendly meal, head to Baba Louie's for pizza and then shop in some of the kid centered stores around town. To explore the area's art galleries, head to Housatoni, which is also where you'll find the town's old paper mill.

There are also a number of great kid-friendly hikes in the area. A favorite for families is Monument Mountain, which isn't far and includes just a slight incline. Also near town are a number of natural swimming areas and skiing.

There are a number of nice vacation rentals for families in the area.

Chic Updated Home in Great Barrington

Great Barrington, Massachusetts
A popular vacation rental in Great Barrington is this beautiful and spacious 3-bedroom, 2-bathroom house that has room for up to 14 people. The views are amazing! Larger groups love the size of this property. This one is a good find for anyone headed to Great Barrington. You can take in the fresh air from the balcony and enjoy some time to unwind.

A fully equipped kitchen lets guests prepare their own meals. All of the bedrooms are nicely furnished. You'll find more than one bedroom with a queen sized bed, too. Also on the list for this house is parking, internet, and a grill.



Stunning Renovated Victorian

Great Barrington, Massachusetts
This gorgeous and historic property would be an amazing option for a large group with all of its extra space. The 5-bedroom, 4-bathroom house has a great location. There's also golf and tennis in the area. Check out the photos! If you love vacationing with your dog, you'll appreciate that is a pet-friendly property as well.

Cook all of your meals in the kitchen, as the microwave, dishwasher, stove, and oven are provided. Everyone can spread out in the living room, dining area, and porch, too. All of the bedrooms offer everything that guests could need. With a king-sized bed in the master, plus queen beds in other bedrooms, everyone will be comfortable. Everyone will enjoy this house's game room. You'll also find amenities such as games, a grill, parking, internet, and a garage.



Lakefront Berkshires Retreat

Great Barrington, Massachusetts
This lakefront house with a dock is a popular option in Great Barrington, as it has 4 bedrooms and 2 bathrooms. If you're planning a trip with the family, you should definitely consider this large house. You'll find nice furnishings in the bedrooms. The queen-sized bed will offer a comfortable night's sleep. The microwave and oven in the full kitchen will let you cook all of your meals if you like.

Parking, internet, and a grill are also included. You'll also find Pleasant and Main and Brick House Pub less than 3 miles away. If you're looking for comfort and convenience, this is a great house.



Deluxe Home with Pool

Great Barrington, Massachusetts
This house is a great place to base yourself during your time in Great Barrington.

The pool is a fantastic addition to the house that everyone will enjoy. Featuring 4 bedrooms and 2 bathrooms, there's plenty of room for up to 8 guests here, so add it to your wish list. There's plenty of space here for the whole family or group to hang out. And with the living room, dining room, and porch, everyone will be able to spread out and relax. You'll find nice furnishings in the bedrooms. There are king-sized beds in two bedrooms, and queen beds in other rooms.

You'll also find amenities such as games, a grill, parking, internet, and a ping pong table. It's hard to find a place like this, so check it out before it's booked up.



Country Castle

Great Barrington, Massachusetts
This unique castle-style Great Barrington house has a number of comfortable touches and a relaxing atmosphere. The 3-bedroom, 3-bathroom vacation rental has a nice long list of features and has room for up to 8 people. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends. Each bedroom offers a comfortable place to relax. You'll find two bedrooms with king-sized beds, and an extra bedroom has a queen. For those who enjoy cooking, there's a full kitchen. And with the nice living room where you can spread out, this house will let you relax and unwind.

You will also find parking, internet, a garage, and a grill at this vacation rental. Places like this get booked up quickly. As an added bonus, your pets are welcome, too.



Open Field House

Great Barrington, Massachusetts
Staying here will make your trip to Great Barrington fun and convenient. This 3-bedroom, 2-bathroom house can fit up to 5 people. This is a family-friendly place with enough room for everyone. Or, it could be good for a group of friends.

Each bedroom offers a comfortable place to relax. The queen-sized beds in two of the bedrooms both have nice mattresses. If you just want to eat in, the fully-equipped kitchen will let you cook all of your meals. With a living room and dining area, there is enough space for guests to relax and hang out. And more amenities are found here such as parking, internet, and a grill.



Great Barrington Apartment

Great Barrington, Massachusetts
This is a 2-bedroom, 1-bathroom apartment that is spacious and gorgeous. It can accommodate up to 5 guests. There's plenty of space here for the whole family or group to hang out. Both bedrooms offer everything that guests could need. The queen-sized beds both have nice mattresses. The living room and dining room, which offers even more space to relax, will make you feel right at home. Guests appreciate the convenience of this property's full kitchen. This amazing apartment has everything you need, and provides it all with style, too.



Downtown GB Apartment

Great Barrington, Massachusetts
Visitors love this apartment and it makes a great place to stay for your vacation in Great Barrington. The 2-bedroom, 1-bathroom vacation rental has room for 5 people. This is a great option for a family as there's room for everyone. Both bedrooms are nicely furnished. With both bedrooms having queen-sized beds, everyone will be able to sleep comfortably. Enjoy cooking your meals in the kitchen, which has modern appliances including a microwave, dishwasher, stove, and oven. With a living room and dining area, there is enough space for guests to relax and hang out.



Williamstown Airbnb's & VRBO's

Williamstown, Mass. is a charming college town in the northern part of the Berkshires. It's a great spot for families who enjoy hiking and museums. The town is home to Williams College, which has some great galleries and museums. In particular, visitors enjoy the Williams College Museum of Art and the Clark Museum, which is just outside of the downtown area.

There are a number of great hiking areas near town as well. Just outside of town is Mt. Greylock, which is the highest peak in Massachusetts. Also nearby are the Taconic Trail State Park, Field Farm, and Bullock Forest.

Williamstown has a wide variety of rental properties to choose from. There are smaller, more affordable condos and apartments, but families usually enjoy the larger houses which offer more bedrooms, larger kitchens, and outdoor space where the entire family can play.

Chic Berkshire Dollhouse

Williamstown, Massachusetts
A popular vacation rental in Williamstown is this spacious 3-bedroom, 2-bathroom house that has room for up to 6 people. This is a great option for a family as there's room for everyone. This is a great spot to enjoy your next trip to Williamstown. Here you'll be situated in a great location close to Williams College and Sterling and Francine Clark Art Institute.

You can either go out to eat or just stay in and cook all of your meals in the kitchen. And with the living room and dining room, everyone will be able to spread out and relax. You'll find nice furnishings in the bedrooms. Several bedrooms have queen sized beds, which is great for everyone to relax. They are very well furnished. A grill, parking, internet, and a garage are also included.



Huge Luxe Williamstown Updated Victorian

Williamstown, Massachusetts
This is a historic 5-bedroom, 5-bathroom house that is roomy and gorgeous. It can accommodate up to 10 guests. This large house is perfect for a big family or group of friends. All of the bedrooms offer everything that guests could need. One bedroom has a king-sized bed and several other rooms have queen beds. There's even more space to hang out in the living room, dining room, and porch. The kitchen is convenient, well stocked, and of course has everything you need to cook all of your own meals. As an added bonus, your pets are welcome, too.



Walk to Downtown & Museums in Williamstown

Williamstown, Massachusetts
People love this house and it makes a great place to stay for your vacation in Williamstown. The 5-bedroom, 3-bathroom vacation rental has room for 16 people. This place is just the right size for a large friends' group getaway. All of the bedrooms offer everything that guests could need. One bedroom has a king-sized bed, while the others have queens. Enjoy cooking your meals in the kitchen, which has modern appliances including a microwave, dishwasher, and stove. There's also the living room and dining area offering more space to guests.

At this place, you'll also have games, a grill, parking, and internet. It's hard to find a place like this, so check it out before it's booked up. This is also a pet-friendly place to stay. Williams College, Williamstown Theatre Festival, and Sterling and Francine Clark Art Institute are within five miles of this place.



11-Acre Mid-Century Estate

Williamstown, Massachusetts
This house on a huge tract of natural land is a popular option in Williamstown, as it has 4 bedrooms and 3 bathrooms. With space for the whole group, this is a great vacation rental for the entire family. All of the bedrooms are nicely furnished. With two of the bedrooms having king-sized beds, everyone will be able to sleep comfortably. You'll be able to cook all of your meals in the fully-equipped kitchen with a microwave, dishwasher, and stove. There's even more space to hang out in the living room, dining room, and porch.

Need a private pool? Doesn't everyone? This place has one, and it's fantastic. Also on the list for this house is a grill, parking, internet, and fire pit. This place is just a few minutes away from Williams College, Pera Mediterranean Bistro, and Spice Root Modern Indian Cuisine. This is a comfortable option for anyone headed to Williamstown.



Tranquil Farmhouse

Williamstown, Massachusetts
This mountain view house is a great place to base yourself during your time in Williamstown. Located less than one mile away you'll find Williams College and Sterling and Francine Clark Art Institute.

Featuring 3 bedrooms and 1 bathroom, there's plenty of room for up to 8 guests here, so add it to your bucket list. There's plenty of space here for the whole family or group to hang out. Guests enjoy the full kitchen which is great for preparing home cooked meals. There's also the living room and dining area offering more space to guests. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. The master has a king-sized bed, and an extra bedroom has a queen.

You will also find internet and a grill at this vacation rental. This one is a good find for anyone headed to Williamstown. And you can bring the furry members of the family, as this place is pet-friendly.



Cozy Renovated Cabin in Williamstown

Williamstown, Massachusetts
If you're looking for a mountain view vacation rental in Williamstown, this 2-bedroom, 2-bathroom cabin is a great option. This is a comfortable option for anyone headed to Williamstown. This is a great option for a family as there's room for everyone. Each bedroom offers a comfortable place to relax. With a queen-sized bed, you'll sleep comfortably. The microwave, dishwasher, and stove in the full kitchen will let you cook all of your meals if you like. And with the nice living room, dining area, and porch where you can spread out, this cabin will let you relax and unwind.

This cabin also has modern amenities such as games, a grill, parking, and internet. You'll also find Williams College, Mount Greylock, Williamstown Theatre Festival, and Sterling and Francine Clark Art Institute less than 5 miles away.



Lee Airbnb's & VRBO's

Lee has a historic downtown and a laid back down-to-earth vibe that visitors love. The downtown has a number of historic buildings including the Congregational Church, the Lee Library, and the Civil War Memorial Hall. There are also a number of Victorian homes in the area.

Outside of the downtown area, visitors enjoy shopping at the nearby outlet mall. There are also a number of restaurants in the area. Kids and adults alike will enjoy spending time at Laurel Lake which offers a quintessential mountain experience.

The Gatehouse on Golden Hill

Berkshire County, Massachusetts
This house is a popular option to base yourself in Lee, as it has 4 bedrooms and 4 bathrooms. This house is a great option for several families traveling together. All of the bedrooms offer everything that guests could need. And with multiple rooms with queen beds, everyone will be able to sleep comfortably. The microwave and oven in the full kitchen will let you cook all of your meals if you like. Parking, internet, and a grill are also included.



Stunning Post & Beam Home

Berkshire County, Massachusetts
Guests love this unique and well-designed house and it makes a great place to stay for your vacation in the Berkshires. The 5-bedroom, 3-bathroom vacation rental has room for 14 people. With room for so many people, this large house is a nice option for families traveling together. Each bedroom offers a comfortable place to relax. One bedroom has a king-sized bed, while the others have queens. One bedroom has bunk beds which the children will love. The kitchen is well stocked with a microwave, dishwasher, stove, and oven. Everyone can spread out in the living room, dining area, and porch, too.

This house also has modern amenities such as games, a grill, and parking. Staying here will make your trip to Berkshire County fun and convenient. The location is very convenient because National Shrine of the Divine Mercy, Lee Prime Outlets, Salmon Run Fish House, and Timothy's Restaurant is less than three miles from here.



Expansive Berkshires Property

Lee, Massachusetts
This is a 4-bedroom, 1-bathroom mountain view house that is large and gorgeous. It can accommodate up to 6 guests. There's plenty of space here for the whole family or group to hang out. You'll find nice furnishings in the bedrooms. One bedroom has a king-sized bed and another has a queen. There's even more space to hang out in the living room and porch. A fully equipped kitchen lets guests prepare their own meals.

You will love hanging out on the balcony, soaking in the atmosphere. This place will quickly feel like a home away from home.



Gorgeous, Private, Family-Friendly, Organic Home

Lee, Massachusetts
For anyone that wants a fun-filled vacation in Lee, this 3-bedroom, 2-bathroom house is a great vacation rental as it can accommodate 6 people. This house is perfect for a large family or friends group. You'll be able to cook all of your meals in the fully-equipped kitchen with a microwave and dishwasher. The 3 bedrooms are nicely laid out so everyone can sleep comfortably. This house also has a living room and dining area, which will let you relax comfortably on your trip. And more amenities are found here such as games, a grill, and parking. This is also a pet-friendly place to stay. Stroll out to the balcony and enjoy the views. With golf and tennis nearby, this is the perfect location to use as your home-base. This is a comfortable option for anyone headed to Lee.



North Adams

North Adams is home to a number of historic churches, giving it a charming skyline. The area is filled with forests, parks, and beautiful landscapes. Visitors enjoy going to the Massachusetts Museum of Contemporary Art, which is the largest contemporary art museum in the country. For kids who enjoy trains, a visit to the Western Gateway Heritage State Park is fun. It's located in the restored freight yard district and has a number of railroad exhibits. Also nearby is Natural Bridge State Park as well as a number of great hiking trails.

Spacious Victorian

North Adams, Massachusetts
This is a historic 4-bedroom Victorian house that is large, beautiful, and stunning. It can accommodate up to 9 guests. This is a large space and would be perfect for a big family, or multiple families on vacation together. The location is perfect, as it's near plenty of nearby activities, shops, and restaurants in the town. Or you can easily drive to the other nearby towns or even up into Vermont.



If you're interested in more accommodation options in Berkshires, you should also see Romantic Places to Stay in the Berkshires for a Couple's Weekend Away.
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The Best Airbnb & VRBO Vacation Rentals in the Berkshires (June 2021) | Budget Your Trip

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