Treetop Hideaway In Tyringham
apartment, Tyringham
This secluded log cabin is located in Lee, offering expansive views of the Tyringham Valley and bordering conservation land in Monterey, a short drive from Greenock Country Club and Otis Ridge.
This spacious retreat features a recently renovated kitchen, a screened porch with a hot tub, a wraparound deck, and over 35 acres of private woods, accommodating up to 8 guests with 4 bedrooms and 1 bathroom.
This spacious retreat features a recently renovated kitchen, a screened porch with a hot tub, a wraparound deck, and over 35 acres of private woods, accommodating up to 8 guests with 4 bedrooms and 1 bathroom.
Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer!
apartment, New Marlborough
This 6-bedroom, 4-bathroom apartment is located in Great Barrington, 10 minutes from the town center and less than 10 minutes from Ski Butternut, with proximity to Bidwell House Museum and Mahaiwe Performing Arts Center.
This spacious rental accommodates 14 guests and features a chef's kitchen with high-end appliances, a 45' x 19' heated seasonal pool, a year-round hot tub, a game room, a bocce field, and a fire pit.
This spacious rental accommodates 14 guests and features a chef's kitchen with high-end appliances, a 45' x 19' heated seasonal pool, a year-round hot tub, a game room, a bocce field, and a fire pit.
Cozy Berkshire Cottage
apartment, Otis
This lake access cottage in the Berkshires is located near cultural attractions and four ski areas, all within a 45-minute drive.
This peaceful retreat offers 1 bedroom, 1 bathroom, and can accommodate up to 6 guests, featuring a fully equipped kitchen, gas fireplace, high-speed Wi-Fi, and seasonal amenities like kayaks and a swim dock.
This peaceful retreat offers 1 bedroom, 1 bathroom, and can accommodate up to 6 guests, featuring a fully equipped kitchen, gas fireplace, high-speed Wi-Fi, and seasonal amenities like kayaks and a swim dock.
Overflow Cabin Retreat On Otis Reservoir
cabin, Otis
This cabin is located in the Berkshires, offering direct access to Otis Reservoir and a private boat ramp within a family-owned campground.
This pet-friendly cottage accommodates four guests with two bedrooms, one bathroom, a full kitchen, air conditioning, and internet, plus access to shared amenities like a beach and playgrounds.
This pet-friendly cottage accommodates four guests with two bedrooms, one bathroom, a full kitchen, air conditioning, and internet, plus access to shared amenities like a beach and playgrounds.
Quaint & Cozy Loft
apartment, Stockbridge
This Stockbridge loft apartment offers stunning views of Norman Rockwell's home and the village street, providing easy access to local attractions.
The one-bedroom, one-bathroom unit features a galley kitchen, fireplace, hardwood floors, and accommodates two guests, perfect for exploring Stockbridge's historical sites and charming village.
The one-bedroom, one-bathroom unit features a galley kitchen, fireplace, hardwood floors, and accommodates two guests, perfect for exploring Stockbridge's historical sites and charming village.
Ridge House At Otis Ridge Ski Area
apartment, Otis
The Ridge House is located right next to the Otis Ridge Ski Area, making it perfect for winter sports enthusiasts. This apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment features a spacious open-plan layout with three bedrooms and can accommodate up to six guests. Amenities include a fully equipped kitchen, a cozy fireplace, a private deck with a grill, and Wi-Fi access.
The apartment features a spacious open-plan layout with three bedrooms and can accommodate up to six guests. Amenities include a fully equipped kitchen, a cozy fireplace, a private deck with a grill, and Wi-Fi access.
Rustic Berkshire Getaway
apartment, Becket
This top-floor apartment is located in the Berkshires, just a short distance from the renowned Jacobs Pillow dance center, numerous lakes and ponds, hiking and biking trails, and skiing opportunities. The apartment has excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen with a fridge and dishwasher, air conditioning, a garden, parking, and a digital guidebook to help you explore the area.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen with a fridge and dishwasher, air conditioning, a garden, parking, and a digital guidebook to help you explore the area.
Berkshires Lodge | Pool, Hot Tub & Fire Pit
apartment, Becket
This spacious 6-bedroom lodge is located in Becket, Massachusetts, just a short drive from Jacob's Pillow and Tanglewood, offering a peaceful escape in the Berkshires. The accommodation has received excellent ratings for location, cleanliness, and overall user experience.
This modern lodge features a fully equipped kitchen, a dedicated study with a twin bed, and a private yard with a hot tub and fire pit. Guests can enjoy the tranquility of the rural setting, explore the nearby Becket Woods, or relax with entertainment options like ping pong and a smart lock for convenient access.
This modern lodge features a fully equipped kitchen, a dedicated study with a twin bed, and a private yard with a hot tub and fire pit. Guests can enjoy the tranquility of the rural setting, explore the nearby Becket Woods, or relax with entertainment options like ping pong and a smart lock for convenient access.
Direct On Lake Garfield: Book Fall Weekends!
apartment, Monterey
This lakefront apartment is located near Lake Garfield, just a short drive from Butternut and Great Barrington. It boasts excellent user, location, and cleanliness ratings, making it a top choice for travelers. The three-bedroom home comfortably sleeps up to six guests and features a large screened-in porch with lake views, a fully equipped kitchen with high-end appliances, and a private dock for swimming, paddleboarding, kayaking, and more.
Enjoy the beautiful scenery and the many amenities, including a gas fireplace, outdoor fire pit, central air conditioning, and high-speed internet.
Enjoy the beautiful scenery and the many amenities, including a gas fireplace, outdoor fire pit, central air conditioning, and high-speed internet.
Misty Pines Cabin | Wood Stove Sauna
cabin, Monterey
This secluded log lodge in Monterey, MA, offers a Berkshire escape minutes from Beartown State Forest, Lake Garfield, and Steadman Pond, with the Bidwell House Museum also nearby. This pet-friendly cabin accommodates up to 8 guests with 3 bedrooms, 3 bathrooms, a full kitchen with a fridge and dishwasher, internet, a garden, parking, and a wood-fired outdoor sauna for relaxation.
Converted Berkshire Schoolhouse On A Quiet River
apartment, New Marlborough
This charming New Marlborough cottage is situated near Great Barrington, offering easy access to Butternut ski resort and the Berkshires' cultural attractions. It consistently receives excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom cottage accommodates up to five guests and features a well-equipped kitchen, a relaxing terrace, and a private garden. Guests can enjoy amenities like a fire pit, a lawn for croquet, and a DVD collection, ensuring a comfortable and enjoyable stay.
The three-bedroom cottage accommodates up to five guests and features a well-equipped kitchen, a relaxing terrace, and a private garden. Guests can enjoy amenities like a fire pit, a lawn for croquet, and a DVD collection, ensuring a comfortable and enjoyable stay.
Berkshires! Walk To Lake, Kayaks, Dog Friendly.
cabin, Becket
This dog-friendly A-frame cottage in Becket, Massachusetts, is located in a private lake community with beach access, a short drive from Lee, Stockbridge, Lenox, and Tanglewood, and near the Appalachian Trail.
The one-bedroom, one-bathroom home sleeps four, features a fully equipped kitchenette (no oven), a private deck, outdoor fire pit, and grill, and provides amenities for canine guests.
The one-bedroom, one-bathroom home sleeps four, features a fully equipped kitchenette (no oven), a private deck, outdoor fire pit, and grill, and provides amenities for canine guests.
