Places to stay in The Berkshires, MA

This three-bedroom, two-bathroom Berkshire retreat is situated on a 1.4 hectare wooded plot near Great Barrington, Massachusetts, a 19km drive from its town centre and within 32-40km of Stockbridge and Lenox.
The property, sleeping six guests, boasts a chef's kitchen, jacuzzi, garden, parking, and a media room that doubles as a third sleeping area; nearby attractions include Tanglewood, Butternut Ski Resort, and Lake Buel.

This two-bedroom apartment is situated in the Sherwood Forest district of Becket, just 0.6 kilometres from the Sherwood Shoppe and within an 8-kilometre radius of Jacob's Pillow.
The 76 square metre property boasts a private backyard with a fire pit, a screened porch, and access to canoes, paddleboards, and life vests for exploring the lake, accommodating up to 7 guests.

This Becket holiday let is situated in a rural, mountainous area, 970 metres from the Becket Land Trust Historic Quarry and 1.1 kilometres from Iroquois Waterfront Beach.
This 93 square metre apartment sleeps five and offers two bedrooms, one bathroom, a living and dining area with a sofa bed, a fully equipped kitchen, air conditioning, complimentary Wi-Fi, a private garden, and a terrace, with nearby access to cultural sites and ski resorts.

This upscale log cabin is located in the Berkshire Mountains, just 24 kilometres from Butternut Ski Mountain and the town of Great Barrington, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for location, cleanliness, and user experience.
The spacious five-bedroom property can accommodate up to 15 guests, making it ideal for families or groups of friends. The cabin is fully equipped with modern amenities including a full kitchen, Wi-Fi, a wood-burning stove, a gas BBQ, and air conditioning in several rooms. Guests can enjoy a range of activities in the surrounding area, including hiking, fishing, boating, and exploring the charming towns of Lenox and Lee.

This historic house is located in the southeast corner of the Berkshires, around 48 kilometres from the nearest shopping centre, offering a peaceful retreat in the beautiful countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has four bedrooms and one bathroom, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a garden, and air conditioning, alongside modern amenities while retaining its authentic colonial charm.

This rustic modern apartment is located in Otis, Massachusetts, just 5 kilometres from Otis Ridge Ski Area and within a 15-kilometre radius of Butternut and Catamount ski resorts, perfect for a winter getaway. The property has received excellent ratings for its cleanliness, location and overall experience.
The apartment can accommodate up to 6 guests and features a spacious layout with a modern kitchen, a cosy fireplace and a large garden. Guests can enjoy the convenience of a fully equipped kitchen, a washer and dryer, and a wrap-around deck with a gas grill, as well as access to a range of activities in the surrounding area, including skiing, hiking and exploring the Berkshires.

This lakefront flat in Otis, Massachusetts, offers direct access to the Otis Reservoir within the scenic Berkshires mountains, boasting stunning lake views and a private dock for watercraft.
This family-friendly dwelling sleeps six, featuring two bedrooms and convertible twin beds, a fully equipped kitchen with fridge, freezer and microwave, a garden with a fire pit and covered deck, plus provided kayaks and WiFi, all within a 5-6 vehicle capacity driveway.

This Sherwood Forest Community flat in Becket is situated in a woodland setting, offering lake access and a 29-kilometre drive to downtown Lee.
This apartment accommodates up to seven guests with three bedrooms, a fully equipped kitchen featuring a microwave and dishwasher, air conditioning, and fibre optic internet, plus it includes a Level 2 EV charger and bicycles for exploring the area.

This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

This Berkshire property offers a peaceful retreat in Becket, situated 25.75 kilometres from Cranwell Spa & Golf Club and 29 kilometres from Tanglewood Musical Center, with Norman Rockwell Museum 30.5 kilometres away and Bradley International Airport 64.37 kilometres distant.
This detached house, spanning 270 square metres, accommodates up to 23 guests with one bedroom, two bathrooms, a fully equipped kitchen, air conditioning, a terrace, and complimentary WiFi and parking.

This four-bedroom apartment is situated in Otis, right on the water in a cove, with a road separating the front yard from the water's edge. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
The self-catering property sleeps up to eight guests and features a fully-equipped kitchen, two bathrooms, and a spacious deck. Guests can enjoy a private dock, boat rentals, and a peaceful garden, all within a safe and child-friendly environment.

This three-bedroom flat in Monterey is located in a district perfect for outdoor pursuits, a 5-minute walk from Lake Garfield beach and a short drive to ski resorts and the cultural hubs of Great Barrington, Lee, Stockbridge, and Lenox.
This property accommodates six guests and features a wood-burning fireplace, a screened-in porch, complimentary kayaks and a paddleboard, and a record collection, with internet, kitchen, and parking provided.