Holiday Rentals in Great Barrington, MA

The Ponds at Foxhollow by Capital Vacations is located in Lenox, Massachusetts, just a short drive from Tanglewood and the Tanglewood Musical Center, making it a great choice for music lovers and those looking to explore the scenic Berkshires. The resort enjoys excellent location and cleanliness ratings, with guests consistently praising its comfortable and well-maintained accommodation.
Each apartment features a fully equipped kitchen and a dining and seating area with a TV, providing everything you need for a relaxing stay. Guests can enjoy a range of amenities, including a seasonal outdoor pool and hot tub, an indoor pool, sauna, fitness center, and tennis court, as well as free bicycle use, fishing, and canoeing opportunities.

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 chalet is situated in a secluded mountainside location in West Stockbridge, just 10 kilometres from hiking trails, boating, swimming, skiing, and shopping. It has received excellent ratings for its location, cleanliness, and overall experience.
The spacious chalet can comfortably accommodate up to 12 guests, offering a modern kitchen, dining area, and a cozy fireplace. Amenities include a ping pong table, board games, a flatscreen TV, a gas grill, and a fire pit, ensuring entertainment for all ages.

This two-bedroom apartment near Copake Lake, New York, is situated approximately 3.2 kilometres from Hillsdale Town Hall, Catamount Aerial Adventure Park, and the community library, and 4.8 kilometres from the Catamount Ski Area and Taconic State Park.
The self-catering flat sleeps four, offering a sofa bed, refrigerator, microwave, stovetop, coffee maker, TV, and dedicated workspace; on-site parking and Wi-Fi are also provided.

This Hillsdale flat, located near the Berkshires and Hudson Valley, is under 16 kilometres from Catamount Aerial Adventure Park and Catamount Ski Area, offering convenient access to outdoor pursuits and local attractions.
This three-bedroom residence accommodates up to six guests, featuring a fully equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and a wood-burning fireplace, perfect for enjoying movie nights with its projector setup or evenings around the outdoor fire pit.

This family-friendly holiday home is situated in the mountains, just 20 kilometres from Catamount Aerial Adventure Park, Catamount Ski Area, and Omi International Arts Center. The property has received excellent user reviews, highlighting its comfortable and relaxing atmosphere.
This one-bedroom house can accommodate up to six guests and features a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy the spa, jacuzzi, and outdoor barbecue facilities, as well as free Wi-Fi and air conditioning.

This four-bedroom woodland cabin is situated in the foothills of the Appalachian Trail, just a short distance from the centre of Great Barrington and its attractions. The property offers a range of amenities including a swimming pool, garden, and parking, as well as climate control in each bedroom and a central air system downstairs, perfect for a family getaway.

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 self-contained apartment is located 1.6 km from the town centre, a short drive from Catamount and Butternut ski resorts, and under 25 minutes from Tanglewood.
The studio features a queen bed, a pull-out sofa bed, a fully equipped kitchen with oven and fridge, a full bathroom, and a washer/dryer; it comfortably sleeps four guests and offers backyard access.

This five-bedroom apartment is situated in New Marlborough, a short drive from scenic hiking trails, swimming lakes, and winter skiing. It has received excellent ratings for user experience, location, and cleanliness.
The apartment has two bathrooms and can comfortably accommodate up to ten guests. It features a fully equipped kitchen, a garden, parking, internet access, and a range of amenities for both indoor and outdoor relaxation, including a fireplace, a porch, a trampoline, a tire swing, and a soccer net.

This secluded lodge near Ghent offers a private 106-hectare estate, located 24-32 kilometres from the Catamount and Butternut Mountain ski resorts.
This four-bedroom, three-bathroom holiday home accommodates seven guests, featuring two kitchens, air conditioning, Wi-Fi, a garden, parking, a fireplace, and access to hiking trails, a pond for swimming, and fishing opportunities.

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.