Romantic Airbnbs in the Berkshires for a Couple's Weekend Away (March 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 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 Airbnbs 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.

Charming Lenox Cottage - an Airbnb in the Heart of Town

Full Kitchen, Outdoor Space
This cute cottage is perfectly located for couples who want to explore everything that Lenox has to offer. It has a well equipped kitchen and a lovely garden.

Romantic Stockbridge Airbnbs

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.

Stockbridge Airbnb Vacation Home

Entire House
This house is a nice option for couples who want a bit more space. It's well located and has a large yard and a beautiful setting.

Hideaway in the Woods - a Classic Berkshire Cabin

3 Bedroom Cabin
This house offers a romantic setting for couples who want to escape to the mountains. There's even a waterfall near the backyard!

Cozy Cottage by the Brook

1 Bedroom, Full Kitchen
This cozy and affordable cottage makes a great retreat for couples who enjoy hiking and natural settings.

Pittsfield - Classic Berkshire Airbnbs

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.

Heart Of The Berkshires - a Pittsfield Airbnb

3 Bedrooms

This apartment is impressively clean and well located. In particular, couples enjoy passing time on the porch.

4-Bedroom Berkshires Home

4 Bedrooms, 2 Bathrooms
For couples who want a lot of space and a large backyard, then this house is a nice option.

Great Barrington's Romantic Airbnbs

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.

Great Barrington Apartment Getaway

Close to Town and Trails
This is a charming cottage apartment with a sunroom and a nice outdoor space. It makes a great base for exploring the town and hiking trails that are nearby.

Pittsfield Modern Apartment

1 Bedroom, Kitchenette
This apartment offers a nice retreat for couples who want to enjoy the natural beauty of the Berkshires. It's a clean but modest space with a small kitchen (no full stove, just a hot plate). If you want to enjoy peaceful walks by the lake, then this is the place for you.

Williamstown - Unique Airbnbs 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 Riverside Cottage

2 Bedroom, Full Kitchen
This adorable cottage offers the quintessential Berkshires experiences. The a babbling brook in the backyard and it's close to everything that Williamstown has to offer.

Cozy Barn Apartment

1 Bedroom, Full Kitchen
This rustic barn apartment has river access, a great yard, and access to all of the best sights around Williamstown.

Modern Loft Apartment

2 Bedroom
This loft apartment offers a trendy atmosphere by a pristine river. It's the perfect place for couples who want to combine luxury living with natural beauty.

Lee - Charming Airbnb Rentals

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.

Cozy Townehouse in the Berkshires

Close to Town
This lovely townhome is perfect for couples who want to enjoy some hiking then head into town for a romantic dinner. It's well maintained, clean, and comfortable.

Charming Renovated Home - A Berkshires Vacation Rental

4 Bedrooms, 2 Bathrooms
For couples that want a bit more space, this home is the perfect place. It's surrounded by nature but also near everything. The kitchen is well appointed if you enjoy cooking, or there are plenty of nearby restaurants to choose from if you're looking for a fun date night.

Private Room in a Charming Berkshires House

Private Bedroom
For an affordable option, this private room is in a charming house. The hosts are wonderful, the location is great, and the setting couldn't be better.

North Adams Airbnbs

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.

Eagle Street Apartment

1 Bedroom
This charming apartment is in a great location that's very walkable, quiet, and convenient. Couples enjoy its accessibility to everything and it's clean and comfortable setting.

The Green House

Secluded Private Apartment
This apartment is perfect for couples. It's in an old Victorian home and it has a quirky and fun style, an open layout, and lots of activities.

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