Holiday Rentals in The Berkshires

This four-bedroom lodge is situated in the Berkshires, a scenic region of Western Massachusetts, about 48 kilometres from Stockbridge, Great Barrington, and Otis Reservoir. The property has received excellent ratings for location, cleanliness, and user experience.
The lodge is spacious and can accommodate up to 12 guests. It offers a range of amenities, including an indoor pool, a billiards lounge, a large dining room, a well-equipped kitchen, and a private garden.

This family-friendly holiday home is situated near Monterey, within a 3km radius of Beartown State Forest and Bidwell House Museum, and within 10km of Ashintully Gardens and McLennan Reservation. The property has received excellent ratings for its cleanliness, location and user experience.
The accommodation has four bedrooms and a floor area of 288 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a fireplace, a patio with a barbecue grill, a fitness centre, and a garden.

This charming cabin in Otis is situated just one lot away from the lake, offering a shared dock and access to the water. The peaceful surroundings provide a tranquil escape from the everyday hustle and bustle.
The two-bedroom cabin can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, air conditioning, and a screened porch, perfect for enjoying the beautiful sunsets.

This secluded apartment in Otis, nestled deep within the southern Berkshires' pine forests and stone walls, offers a tranquil escape on a private 6-acre property, providing a convenient base for exploring the region.
This 3-bedroom, 3-bathroom dwelling accommodates up to 10 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and indoor entertainment including a climbing wall and playroom, all within a cabin experience designed for family adventures.

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 renovated lakeside property is located in New Marlborough, just 26 kilometres from both Cranwell Spa & Golf Club and Tanglewood Musical Center, offering a peaceful retreat close to popular attractions. The house has received excellent user and location ratings, and a very good cleanliness rating.
This four-bedroom home spans 130 square metres and comfortably accommodates eight guests. Enjoy a range of amenities, including a fully equipped kitchen, a terrace with lake views, a fitness centre, and a private dock for swimming, fishing, or simply relaxing by the water.

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 log cabin, nestled in the district of Monterey bordering Tyringham, is located within a short drive of attractions like Greenock Country Club, Otis Ridge, Ashintully Gardens, and Berkshire Scenic Railway Museum. This secluded dwelling, situated on 35+ acres of woodland, offers a peaceful retreat with stunning views of the Tyringham Valley, a spacious living area with vaulted ceilings and a fireplace, a modern kitchen, a screen porch with a hot tub, and a wraparound deck.

This luxurious five-bedroom chalet is situated on Lake Garfield in the Berkshires, approximately 11km from Butternut and 24km from Catamount ski resorts, near Great Barrington.
Sleeping up to 14 guests, this modern property boasts a fully equipped chef's kitchen, four bathrooms, two living rooms, a hot tub, and access to kayaks and paddleboards (summer season only), offering a perfect base for exploring the Berkshires.

This luxurious apartment is located in the picturesque Berkshires of western Massachusetts, 32 kilometres from Great Barrington, a town known for its cultural experiences, restaurants, and shops. The apartment offers a range of amenities including a hot tub, steam room, radiant heated floors, three fireplaces, a fully equipped chef's kitchen, a gym, a 2-car heated garage, a children's nook with books and games, a dedicated kids room with 6 queen over queen bunk beds, accommodating up to 12 guests, and a great room with a pool table, foosball, darts, arcade games, an 85” TV, and a wet bar with a wine fridge and a kegerator.

This Monterey lodge is located among tall pines, a short distance from Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This three-bedroom, three-bathroom holiday home accommodates eight guests and features a fully equipped kitchen, a wood-fired sauna, a garden, and parking, with a rustic log cabin feel and an outdoor wood-fired sauna for relaxation.

This apartment is located in the Berkshires, a region in western Massachusetts, just 160 kilometers from Monterey, offering stunning views of Lake Garfield. It has received excellent ratings for its location, cleanliness and overall guest experience.
The property is a spacious home with a modern design, suitable for up to 12 guests. Enjoy a range of amenities, including a hot tub, sauna, a fully equipped kitchen, a large deck with a BBQ grill, a ping pong table, and a pool table for entertainment.

This charming cabin is situated in Great Barrington, Massachusetts, just a short drive from attractions like the Norman Rockwell Museum and Tanglewood Musical Center, offering a peaceful escape in a picturesque setting. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The four-bedroom, two-bathroom lodge provides ample space for up to 10 guests, with a total floor area of 153 square metres. The cabin offers a range of amenities, including a fully equipped kitchen, a spacious deck, a garden, air conditioning, and free Wi-Fi, making it ideal for families or groups looking for a comfortable and relaxing stay.

This three-bedroom cottage is situated on the shores of Otis Reservoir, Massachusetts' largest recreational lake, just 40 kilometres from the Berkshire Hills.
The property offers direct lake access with two docks, a spacious deck with sunset views, a private hot tub, and complimentary kayaks for exploring the scenic surroundings.

This Monterey mountain property is situated 0.6km from Lake Buel, and within 5km of Dry Hill, Les Trois Emme Winery, Ski Butternut, and Beartown State Forest.
This three-bedroom house, sleeping six, boasts a fully equipped kitchen, private patio, fireplace, free Wi-Fi, and is ideal for families or groups enjoying nearby water sports, wine tasting, skiing, or forest walks.

This three-bedroom apartment is situated in a peaceful neighbourhood near Otis Ridge Ski Area, a short walk from the slopes and a scenic drive from Great Barrington, Tanglewood, and Jacob's Pillow. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment comfortably sleeps up to seven guests and features a well-equipped kitchen, a private garden, a hot tub with mountain views, a spacious deck, and a fireplace. Guests can enjoy a range of activities including skiing, exploring the surrounding mountains, and visiting nearby cultural attractions.