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This apartment is located in Great Barrington, a short 10-15 minute drive from the town center, with Monument Mountain nearby. It's rated excellent for location, cleanliness, and user experience.
This 4-bedroom, 4-bathroom home comfortably sleeps 8 guests. The apartment has a fully equipped kitchen, a swimming pool, a garden, a fitness center, and a Tesla EV charger.

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 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 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 waterfront Cape Cod-style house is situated in the heart of Lenox, within walking distance of the Edith Wharton Estate and a short drive from Lee's cultural attractions and outdoor activities. The house has an excellent user rating.
The house has a floor area of 2700 square feet and can accommodate up to 14 guests. It has 5 bedrooms, 3 bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a jacuzzi, a garden, and parking. The house also offers amenities such as a pool table, HD Smart TVs, wood-burning fireplaces, a wine cooler, a hot tub, an outdoor barbecue, a tennis court, kayaks, canoes, and a rowboat.

This story-rich apartment in a rural area of Great Barrington offers convenient access to Ski Butternut (3 miles), downtown Great Barrington (8 miles), and significant Black History landmarks like the W.E.B. Du Bois Boyhood Homesite (15 miles).
This 1750 square foot residence accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, Wi-Fi, a washer/dryer, an indoor gas fireplace, and an outdoor dining area.

This historic brick house is located in the Berkshires of Western Massachusetts, just minutes from Great Barrington and close to the Connecticut and New York borders, offering a peaceful retreat in a picturesque setting. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious home features 4 bedrooms and can accommodate up to 8 guests, providing ample space for families or groups of friends. The home offers a variety of amenities, including a swimming pool, tennis court, fitness center, and a studio building with an art library and living room, making it perfect for relaxation, recreation, and entertainment.

This beautifully restored 1800s colonial house in New Marlborough, Massachusetts, is conveniently located near cultural attractions like Tanglewood, Jacob's Pillow, and Kripalu.
This four-bedroom, two-bathroom home sleeps eight guests and features a spacious open-plan kitchen, dining area, living room with a cathedral ceiling, a full kitchen with dishwasher, laundry facilities, Wi-Fi, a wood-burning stove, and extensive outdoor space with a garden.

This newly remodeled farmhouse is located in a quiet neighborhood on the north side of Great Barrington, just a 5-minute drive from downtown and Butternut Ski Mountain. The home features a spacious open floor plan with a chef's kitchen, a dining room table that seats many, and a comfortable living room, perfect for family gatherings. The farmhouse comfortably sleeps 9 guests and offers a large fenced yard with a stone patio, fire pit, and BBQ for summer cookouts. Modern amenities include a Viking stove, farmer's sink, dishwasher, radiant heated floors, and a dedicated workspace in the primary bedroom.

This historic 1815 barn apartment in South Lee, MA, offers direct access to the Appalachian Trail and is located 2 miles from Stockbridge and 3 miles from downtown Lee, with Goose Pond and October Mountain State Forest 6 miles away.
This 900 sq ft, 1-bedroom loft studio accommodates up to 4 guests with a king bed and futon, featuring a kitchenette, air conditioning, Wi-Fi, a laptop-friendly workspace, and mountain and river views, with pets allowed for an additional fee.

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 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 four-bedroom cabin is located in the foothills of the Appalachian Trail, a short drive from the center of Great Barrington, Massachusetts.
The cabin offers a spacious and modern design with 30-foot ceilings, a refinished swimming pool, and multiple patios, decks, and balconies for outdoor enjoyment.

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 2-bedroom apartment offers a prime location at the base of the ski resort, just 5 miles from Hillsdale and Copake, NY, and Egremont, MA, with Great Barrington, MA, 15 miles away.
This pet-friendly rental accommodates up to 7 guests with two queen beds and a bunk with trundle beds, featuring a full kitchen, air conditioning, and a garden, making it ideal for families seeking ski resort access and proximity to local towns.

This house in Great Barrington is conveniently located within walking distance of the Mahaiwe Performing Arts Center, the Housatonic River Walk, and the Housatonic River, placing you right in the heart of the town's cultural and recreational scene. The home has received excellent ratings for location, cleanliness, and overall user experience.
This 1500 square foot house has 3 bedrooms, 2 bathrooms, and can comfortably accommodate up to 11 guests. The property includes a fully equipped kitchen, a garden, a fireplace, and a barbecue grill, making it perfect for relaxing and enjoying the outdoors.