Vacation rentals in Great Barrington, MA

This spacious home is located in the "Hill" neighborhood of Great Barrington, a short walk from Lake Mansfield and a quick drive to downtown shops and restaurants. The apartment has received excellent ratings for its amenities and location.
This 5000 square foot home comfortably accommodates up to 12 guests with five bedrooms and five bathrooms. It features a gourmet kitchen, a screened porch, a private patio with a hot tub, a tennis court, and a playset for children.

This charming cottage-style apartment in Lee, Massachusetts is conveniently located near Greenock Country Club, Wyndhurst Golf & Club, and McLennan Reservation. Guests consistently rate this property as "very good", making it a popular choice for travelers. This home offers five bedrooms, including a primary suite, and can comfortably accommodate up to 12 guests. Enjoy a spacious kitchen, a relaxing fire pit, a hammock for lounging, and a yard perfect for outdoor games.

This Stockbridge vacation home offers a central location, within a 10-minute walk of Schantz Galleries, the Housatonic River, and Mission House, and less than a mile from the Berkshire Theatre Festival and Naumkeag Museum.
This five-bedroom, two-bathroom house sleeps twelve guests and includes amenities such as free WiFi, a fully equipped kitchen with a refrigerator and dishwasher, a fireplace, and a washing machine; housekeeping is available upon request.

This family-friendly vacation home is located just 20 kilometers from Catamount Aerial Adventure Park, Catamount Ski Area, and Omi International Arts Center, offering a peaceful mountain retreat near popular attractions. The house has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
This one-bedroom, one-bathroom house can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities, including a fully equipped kitchen, a spa tub, a fireplace, a terrace, a garden, and parking, ensuring a relaxing and enjoyable stay.

This secluded 4-bedroom, 3-bathroom cabin is located in the foothills of East Mountain, offering privacy and natural beauty just a short distance from the Great Barrington town center.
This spacious accommodation accommodates up to 8 guests and features a seasonal swimming pool, private hiking trails connecting to the State Forest, expansive 30-foot ceilings with skylights, a wood-burning fireplace, and multiple outdoor areas for enjoying the Berkshires.

This pet-friendly vacation home in Copake Falls offers immediate access to winter sports, situated just a 1-minute walk from Catamount Ski Area and 11 minutes from Catamount Aerial Adventure Park.
This 3-bedroom, 2-bathroom apartment accommodates up to 7 guests and features a full kitchen, air conditioning, Wi-Fi, a swimming pool, and a garden, with on-site parking available.

This pet-friendly vacation home in Copake Falls offers immediate access to winter sports, situated just a 1-minute walk from Catamount Ski Area and 11 minutes from Catamount Aerial Adventure Park.
This 3-bedroom, 2-bathroom apartment accommodates up to 7 guests and features a full kitchen, air conditioning, Wi-Fi, a swimming pool, and a garden, with on-site parking available.

The Ponds at Foxhollow By Capital Vacations is located in Lenox, Massachusetts, just 2.5 miles from the renowned Tanglewood music venue. The resort has received very good user ratings, with excellent ratings for its location and very good ratings for cleanliness.
The resort offers a variety of accommodations, including villas and apartments. Guests can enjoy a range of amenities, including indoor and outdoor pools, a fitness center, a sauna, and free bicycle rentals.

Undermountain Lodge is a short drive from Mount Washington's cultural attractions like Ashley House and Mahaiwe Performing Arts Center, and sits between two natural spring lakes in Sheffield, offering a serene escape. The lodge has earned excellent user ratings.
The four-bedroom cabin comfortably sleeps 12 guests and features a spacious living room, dining room, and well-equipped kitchen. Guests can enjoy the expansive deck, covered porch, and firepit, as well as amenities like free Wi-Fi and a full kitchen with modern appliances.

This Scandivian-inspired house is located in Egremont, Massachusetts, a short walk from a country store and park, and minutes from Great Barrington and Hillsdale for dining and exploring.
This five-bedroom, four-bathroom home sleeps ten guests and boasts a great room, recreation room, extensive amenities including a terrace with firepit, and gigabit internet; enjoy contactless check-in and 24/7 support.

This five-bedroom, three-bathroom home in New Marlborough, Massachusetts, is a beautifully restored 1911 house situated on five private acres, 15 minutes from Great Barrington and adjacent to the farm-to-table restaurant Cantina 229.
The 2,584-square-foot residence boasts a spacious layout, accommodating up to 10 guests and featuring a fully equipped kitchen, a basement with games and laundry facilities, and access to outdoor amenities including a fire pit and expansive lawns; nearby activities include hiking and skiing in the Berkshires.

This Hillsdale rental is located near the Berkshires and Hudson Valley, offering 3 bedrooms and 2 bathrooms for up to 6 guests.
Enjoy a wood-burning fireplace, projector, outdoor fire pit, and fast WiFi in this modern mid-century designed home, perfect for exploring nearby hiking trails and nature.