Romantic Places to Stay in the Berkshires for a Couple's Weekend Away (June 2021)

Stockbridge, Lenox, Williamstown, Great Barrington, and More
Couples looking for a romantic getaway will appreciate the Berkshires beautiful setting with its quaint towns, excellent restaurants, and lively festivals. Whether you're interested in hiking and nature, museums, or cuisine, the Berkshires is a great destination.

There is no shortage of Airbnb and VRBO cabins, houses, cottages, condos, and more to choose from in the area. Many places are within walking distance to a town, while others are nestled in a more rustic setting near nature and hiking trails.

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

Lenox Airbnb's and rentals for Couples

Lenox is one of the most popular towns for couples looking for a romantic retreat. The town is small and charming with a quaint downtown area that's perfect for walks. You'll enjoy the historic New England architecture that gives the community its quintessential character. This town is also known for its local restaurants, health spas, and art venues as well as the Tanglewood Music Festival, which features the Boston Symphony Orchestra.

Nature lovers will enjoy the hiking trails in the area. There is also horseback riding that many couples enjoy.

There are a number of cute cottages and larger houses available for rent in Lenox. If you want space, you can spend more and have a villa to yourselves. There are also smaller cottages that are charming and more affordable for couples.

Historical Downtown 1-Bedroom

Lenox, Massachusetts
A popular place to stay for couples in Lenox is this roomy 1-bedroom, 1-bathroom apartment. This spot is perfect for a couples retreat when you need some privacy. Check out the photos! You'll be close to plenty of things to do because nearby you'll find shopping and restaurants along with Tanglewood Music Center, National Shrine of the Divine Mercy, Lee Prime Outlets, Zinc, and Haven.

You can either go out to eat or just stay in and cook all of your meals in the kitchen. The bedroom is a comfortable place to relax, too. At this apartment, you'll also have parking and internet.



Renovated Downtown 1-Bedroom in Lenox

Lenox, Massachusetts
This is a gorgeous 1-bedroom, 1-bathroom apartment that is spacious and delightful. With just the right amount of space, this apartment is a great option for a couple looking to explore the Berkshires. And with a nice bedroom, guests can unwind after a busy day. Plenty of other nice amenities are also included, so check it out.



Romantic 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. Another popular activity is 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 and it makes for a perfect date night.

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

There are a number of large houses available for rent near Stockbridge, as well as smaller cottages that couples enjoy. Below are a couple of our favorites.

One Block from Main St. in Stockbridge

Stockbridge, Massachusetts
This 2-bedroom, 2-bathroom house can fit up to 3 people. This property is a nice and affordable historic and charming house for a couple or smaller family. It also has a great location!



Villa with Access to 2 Pools

South Lee, Massachusetts
A popular vacation rental with modern amenities is this large 1-bedroom, 1-bathroom villa that offers plenty of comforts. This villa is perfect for couples getaway. The fully equipped kitchen has everything you need such as a refrigerator and microwave. The building's complex offers an indoor pool, game room, and other nice activities so that you can have fun in between exploring the towns of the Berkshires.



Completely Renovated Historic Home

Stockbridge, Massachusetts
People love this renovated historic home and it makes a great place to stay for your vacation in Stockbridge. The 2-bedroom, 2-bathroom vacation rental has room for a couple or even a small family. This house is perfect for couples getaway in Stockbridge. Each bedroom offers a comfortable place to relax. With a queen-sized bed, you'll sleep comfortably. Guests appreciate the convenience of this property's full kitchen. With a living room, dining area, and porch, there is enough space to relax and hang out.



Pittsfield - Classic Berkshire Airbnb's & VRBO's

Pittsfield is the largest city in the Berkshires, but it still has plenty of charm and character. For couples who enjoy keeping busy, this is a fun city to visit. 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 to enjoy. There are also some excellent restaurants in town.

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.

Berkshire Village Carriage House

Lanesborough, Massachusetts
This 1-bedroom, 1-bathroom place is a great option. It will quickly feel like a home away from home. This property has hundreds of reviews from other guests, it should be on your list because it has earned such an excellent rating. This is the perfect place for a couple looking for a romantic and affordable place to stay. The bedroom is a nice place to relax. The kitchen is convenient, well stocked, and of course has everything you need to cook all of your own meals. There's also the dining area offering more space to guests. You'll also find amenities such as parking, fire pit, internet, and a grill. Not too far away you'll find Jiminy Peak Mountain Resort, Berkshire Museum, Tanglewood Music Center, and Bousquet Ski Area.



Charming Berkshire Getaway with Scenic Lake Views

Pittsfield, Massachusetts
This house on the lake is a popular option in Pittsfield, as it has 2 bedrooms and 1 bathroom. This property is a nice and affordable house for a couple or smaller family. Both bedrooms are nicely furnished. The queen-sized bed will offer a comfortable night's sleep. The kitchen in this house is very nice, and with a microwave, oven, and refrigerator you'll be able to cook your meals, too. The location is very convenient because Berkshire Museum, Flavours of Malaysia, and Mission Bar & Tapas is less than three miles from here. Places like this get booked up quickly.



Exquisite Apartment in Grand Victorian

Pittsfield, Massachusetts
This is a 2-bedroom, 1-bathroom apartment in a historic home that is roomy and amazing. It can accommodate up 4 guests. This is an ideal spot for a couple because of its charm and ambiance. You'll find nice furnishings in both bedrooms. With a queen-sized bed, you'll sleep comfortably. Places like this get booked up quickly. It's also located right in the heart of town, close to shops and restaurants.



Historic Red Schoolhouse in Pittsfield

Pittsfield, Massachusetts
This historic schoolhouse has been featured on HGTV. It's renovated, updated, and modern but still retains its historic country charm. It's perfect for a couple or perhaps even a small family. The microwave, oven, refrigerator, and dishwasher in the full kitchen will let you cook all of your meals if you like. And with the nice living room and dining area where you can spread out, this house will let you relax and unwind. The bedroom is a nice place to relax, too. Also on the list for this house is parking and a grill. This is also a pet-friendly place to stay.



Great Barrington's Romantic Places to Stay

Great Barrington has one of the larger downtowns in the Berkshires. There are plenty of restaurants, shops and activities to choose from that make for great date nights. You can wander through the town's art galleries and pop into a number of charming stores.

There are also a number of great hikes, natural swimming spots, and skiing options in the area. Rental properties are a great way to fully experience this town. Some of our favorites are listed below.

Barn Apartment in Gorgeous Stonybrook Farm

Great Barrington, Massachusetts
With room for 2 people, this is a 1-bedroom mountain view apartment that makes for a perfect Great Barrington vacation rental. This apartment has all of the comforts a couple would need. The full kitchen is well stocked and convenient, and features a microwave and dishwasher. The well-furnished bedroom is a nice space to unwind. Enjoy meals or relaxing in this property's living room and dining area. This apartment is perfect for couples getaway in Great Barrington. Parking and internet are also included.



Romantic Berkshires Cottage

Great Barrington, Massachusetts
This cottage is a popular option in Great Barrington, as it has 1 bedroom and 1 bathroom. This cottage is perfect for couples getaway in Great Barrington. With a nice bedroom, guests can unwind after a busy day. The queen-sized bed is a nice touch. The microwave, oven, and refrigerator in the full kitchen will let you cook all of your meals if you like. You'll also be able to spread out through the living room and dining area.

The swimming pool is nice to have, too. Also on the list for this cottage is games, a grill, and parking. And you can bring the furry members of the family, as this place is pet-friendly. This location is also close to golf and tennis. Located less than five miles away you'll find Butternut Ski Resort, Allium, and Baba Louie's. It's hard to find a place like this, so check it out before it's booked up.



Near Main Street, Great Barrington

Great Barrington, Massachusetts
This mountain view apartment is a great place to base yourself as a couple during your time in Great Barrington. Featuring 1 bedroom and 1 bathroom, this is a nice spot with plenty of room for two. The kitchen is convenient, well stocked, and of course has everything you need to cook all of your own meals. With a nice bedroom, guests can unwind after a busy day. The queen-sized bed is a nice touch. Other amenities include parking and a fire pit. Staying here will make your trip to the Berkshires fun and convenient.



Williamstown - Unique Airbnb's & VRBO's for Couples

Williamstown is a charming college town in the northern part of the Berkshires. It's a great spot to escape for a romantic week or weekend. There's plenty of hiking and museums in the area, as well as the prestigious 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.

A number of great hiking areas are 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, as well as larger houses, which offer more room and outdoor space.

Cozy and Quaint Country Cottage

Williamstown, Massachusetts
For a small town getaway, check out this house. This is a 2-bedroom, 1-bathroom mountain view house that is an ideal spot for a couple. With a queen-sized bed, you'll sleep comfortably. This house also has a living room and dining area, which will let you relax comfortably on your trip. For those who enjoy cooking, there's a full kitchen. As an added bonus, your pets are welcome, too.

You'll be close to plenty of things to do because you can walk around town to the shops and restaurants. Also within five miles you'll find Williams College, Mass MoCA, Pera Mediterranean Bistro, and Spice Root Modern Indian Cuisine. This is a great spot to enjoy your next trip to Williamstown.



Lee - Charming Airbnb Rentals and VRBO Places to Stay

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, which are perfect for couples who enjoy unique dining experiences. Laurel Lake is another fun place to hang out and it offers a quintessential mountain experience.

There are a number of vacation rentals to choose from in Lee. Below are a just a few of our favorites.

Elegant 19th Century New England Vacation Rental

Lee, Massachusetts
Meet the friendly locals and enjoy the small town charm at this beautiful apartment in a historic house. Check out the photos! This is an ideal spot for a small family or a couple. The bedroom is a nice place to relax. And more amenities are found here such as parking, internet, and a grill. If you love vacationing with your dog, you'll appreciate that is a pet-friendly property as well.



Garfield House Studio

Lee, Massachusetts
Guests love this studio and it makes a great place to stay for your vacation in Lee. The 1-bedroom, 1-bathroom vacation rental has room for 2 people. Couples love this place. This studio is effeciently furnished as well The large king-sized bed is perfect for couples that enjoy space. The queen-sized bed will let you relax and enjoy your trip. The fully equipped kitchen has everything you need such as a microwave, oven, and refrigerator. This studio also has a porch, which will let you relax comfortably on your trip. The apartment also includes parking and internet. Places like this get booked up quickly. It's also pet-friendly, so bring your furry friend!



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, which many couples enjoy exploring. Art enthusiasts really enjoy the Massachusetts Museum of Contemporary Art, which is the largest contemporary art museum in the country. Also nearby are great hiking trails as well as Natural Bridge State Park.

Meadowhust Farm

Clarksburg, North Adams, Massachusetts
For a unique getaway in the Berkshires, couples can stay on this gorgeous rural property in this 1-bedroom, 1-bathroom house that has room for 2 people. This house is perfect for couples getaway in North Adams as you can take in the views, the rural atmosphere, the agricultural lifestyle, and more. It's hard to find a place like this, so check out the photos to see if it's right for you.

The full kitchen is well stocked and convenient, and features a microwave, oven, and refrigerator. Everyone can also relax in the living room and dining area. You'll enjoy a good night's sleep in the relaxing bedroom. Parking, internet, and games are also included.



For more ideas about places to stay in Berkshires, you might also be interested in The Best Airbnb's & VRBO's in the Berkshires.
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