Vacation Rentals in Great Barrington, MA

This Great Barrington flat offers a private upstairs suite with excellent user ratings, situated a short drive from cultural attractions such as Tanglewood, Shakespeare & Co, the Norman Rockwell Museum, Jacob's Pillow, and Ski Butternut, and within walking distance of the Mahaiwe Performing Arts Centre and the W.E.B. Du Bois Boyhood Homesite.
This 28 square metre, one-bedroom, one-bathroom apartment accommodates two guests and features on-site amenities including a coffee and tea bar, games, a flatscreen television, air conditioning, and parking, with a stylish bathroom boasting a rain head shower and heated floor.

This renovated mid-century motel is located a mile and a half from the centre of Great Barrington, making it an ideal base for exploring the town's shops, restaurants and cultural attractions. The Mahaiwe Performing Arts Centre is just a short walk away.
This apartment, which can accommodate two guests, is ideal for a relaxing getaway. It features a king-size bed, a fully equipped kitchen, a swimming pool, and high-speed internet. Guests can also enjoy nearby skiing at Butternut Ski Resort.

This five-bedroom home is situated on a quiet cul-de-sac just a short walk from the centre of Great Barrington, offering easy access to shops, restaurants, and cultural attractions. The property has received excellent ratings for its cleanliness, location, and overall experience.
The spacious apartment has four bathrooms and can comfortably accommodate up to 12 guests. It offers a range of amenities, including a chef's kitchen, a hot tub, a large screened porch, a private stone patio with a BBQ, and a well-stocked library.

This one-bedroom apartment is located in Great Barrington, just a short drive from the town centre and the Mahaiwe Performing Arts Centre, making it an ideal base for exploring the Berkshires. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is comfortably furnished to accommodate two guests and features a stylish modern design. Enjoy the convenience of a well-equipped kitchen, a private garden, and access to a swimming pool and high-speed internet.

This Great Barrington apartment, a stylish mid-century modern unit in a renovated motel, is situated 2.4km from the town centre, 2.1km from the Mahaiwe Performing Arts Centre, and within easy driving distance of Butternut Ski Resort and Tanglewood.
The self-catering flat offers a king-size bed, SMEG coffee maker, mini-fridge, high-speed internet, a 58" TV with Hulu Live, and accommodates two guests, perfect for exploring the Berkshires.

This stylishly renovated apartment is located in Great Barrington, just a short walk from the town centre and the Mahaiwe Performing Arts Centre, making it a great base for exploring the area. The apartment has consistently received excellent ratings from guests for its cleanliness, location and overall experience.
The apartment can comfortably accommodate two guests in a king-sized bed and features a modern design with local artwork and amenities such as a 58-inch TV with Hulu Live, high-speed internet, and a SMEG coffee maker with local coffee, cream and sugar. Guests can also enjoy access to a shared space with a microwave, ice and water dispenser, and luggage storage.

This Great Barrington apartment, a stylish mid-century modern flat, is situated 2.4 kilometres from the town centre and 2.1 kilometres from the Mahaiwe Performing Arts Centre.
The self-catering unit sleeps two guests and boasts a king-size bed, SMEG coffee maker, 58-inch TV with Hulu Live, high-speed internet, and a shared guest area with microwave and ice/water facilities.

This four-bedroom apartment, a tastefully redesigned 1900 factory conversion, enjoys a riverfront location in Great Barrington, Massachusetts, approximately 8km from Butternut, 16km from Catamount, and 48km from Bousquet ski resorts.
The self-catering property sleeps eight guests and features two bathrooms (one with a bath), a fully equipped kitchen including a dishwasher, a grand piano, a fenced garden, on-site parking for six cars, and a full-size washer/dryer; dogs are welcome.

This stylish studio apartment is situated just a short walk from downtown Great Barrington, with easy access to restaurants, shops and the Mahaiwe Performing Arts Centre. It consistently receives excellent ratings for its location, cleanliness and overall experience.
This modern studio sleeps two guests comfortably and features a king-sized bed, a 58-inch TV with streaming services, high-speed internet, a desk with a window view and a shared space with a microwave, ice and water dispenser. Guests can enjoy local coffee, cream and sugar, and benefit from flexible check-in and check-out times.

This four-bedroom house in Great Barrington, Berkshire County, enjoys a central location offering easy access to the town's shops and restaurants.
The 4-bedroom, 3-bathroom property sleeps six guests and boasts a private swimming pool, fully equipped kitchen, and ample space for family gatherings, all within a peaceful setting.

This stylish one-bedroom apartment is located just 1.6 kilometres from the centre of Great Barrington and 2.1 kilometres from the Mahaiwe Performing Arts Centre, offering easy access to restaurants, shops, and cultural attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment is ideal for couples, offering a comfortable king-size bed with high-quality linens. Guests can enjoy amenities such as air conditioning, a garden, a swimming pool, parking, and high-speed internet.

This spacious five-bedroom house is located in the Hill neighbourhood of Great Barrington, just 1.6 kilometres from Lake Mansfield and 2.4 kilometres from the town centre. It has received excellent reviews from previous guests.
The house spans 465 square metres and comfortably accommodates up to 12 guests. It offers a range of amenities, including a gourmet kitchen, a Jacuzzi, a garden, a spa, a tennis court, and parking.