
Greenwater Pond, MA
10/10 – 10/18
$227/nighttotal: $1816 (8 )
A-frame Cabin W/ Furnished Deck In Becket!
2 2cabin , Becket
This Becket, Massachusetts cabin is conveniently located one mile from Pyramid Lake and two miles from Jacob's Pillow, offering easy access to other attractions like Iroquois Waterfront and Becket Quarry within six miles.
This 1100-square-foot vacation rental boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, a terrace, and a garden with barbecue grills.
This 1100-square-foot vacation rental boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, a terrace, and a garden with barbecue grills.

Greenwater Pond, MA
06/17 – 06/20
$398/nighttotal: $1194 (3 )
A Magical Spot On Little Robin Lake
1 2apartment , Becket
This secluded cottage is located in the Berkshires, near Becket, and is within a 5-minute drive of Jacob's Pillow Dance Festival, a 15-minute drive from the Dream Away Lodge, and a 25-minute drive from Shakespeare and Co and Tanglewood. It has earned excellent ratings for location, cleanliness, and user experience.
The cottage features a single-story open plan downstairs and a spacious second floor with a queen bedroom and a bathroom with granite countertops, accommodating up to 5 guests. Enjoy the lakeside fire pit, swimming in the lake, and relax in the cozy fireplace, jacuzzi, and sunroom.
The cottage features a single-story open plan downstairs and a spacious second floor with a queen bedroom and a bathroom with granite countertops, accommodating up to 5 guests. Enjoy the lakeside fire pit, swimming in the lake, and relax in the cozy fireplace, jacuzzi, and sunroom.

Greenwater Pond, MA
10/10 – 10/18
$511/nighttotal: $4088 (8 )
Waterfront Cottage Retreat By Evergreen Home
3 2apartment , Becket
This Becket, Massachusetts lakefront home sits on Shaw Pond, nine minutes from local shops and restaurants, and 25 minutes from Butternut and Bousquet ski resorts.
The three-bedroom, one-bathroom vacation rental sleeps six, features a full kitchen with modern appliances, a screened porch with lake and mountain views, kayaks, a paddle boat, and direct lake access with a private dock (summer).
The three-bedroom, one-bathroom vacation rental sleeps six, features a full kitchen with modern appliances, a screened porch with lake and mountain views, kayaks, a paddle boat, and direct lake access with a private dock (summer).

Greenwater Pond, MA
06/17 – 06/20
$331/nighttotal: $993 (3 )
Cozy Lake Side Cabin
1 2cabin , Becket
This lakefront cottage in Becket, MA, is located less than 15 minutes from the Massachusetts Turnpike and the town of Lee, offering easy access to area attractions.
The 2-bedroom, 1.5-bathroom retreat sleeps six, features a fully equipped kitchen with modern appliances, fiber optic internet, two fire pits, a canoe, kayaks, a pedal boat, and ample parking; enjoy a sunroom and bonus room for added living space.
The 2-bedroom, 1.5-bathroom retreat sleeps six, features a fully equipped kitchen with modern appliances, fiber optic internet, two fire pits, a canoe, kayaks, a pedal boat, and ample parking; enjoy a sunroom and bonus room for added living space.

Greenwater Pond, MA
08/19 – 08/26
$262/nighttotal: $1834 (7 )
Downtown Gateway To The Berkshires. Walk To Everything.
2 2apartment , Lee
This newly renovated two-bedroom apartment is located downtown in Lee, Massachusetts, steps from local dining and shopping, and within easy reach of the Berkshire Botanical Gardens, Bidwell House Museum, and Tanglewood.
This unit accommodates up to four guests with two bedrooms, one bathroom, and features a fully equipped eat-in kitchen, air conditioning, complimentary Wi-Fi, and is provided with linens and towels for convenience, offering access to biking, fishing, and hiking in the Berkshires.
This unit accommodates up to four guests with two bedrooms, one bathroom, and features a fully equipped eat-in kitchen, air conditioning, complimentary Wi-Fi, and is provided with linens and towels for convenience, offering access to biking, fishing, and hiking in the Berkshires.

Greenwater Pond, MA
10/10 – 10/18
$310/nighttotal: $2480 (8 )
The Meadows House @ Otis Ridge W/ 7-person Hot Tub
4 2apartment , Otis
This vacation home is located in the mountains, just half a mile from Otis Ridge and within a 6-mile radius of County Beach and Ashintully Gardens, offering a peaceful retreat surrounded by natural beauty. The property has received excellent user ratings, indicating a high level of satisfaction among previous guests. This 3-bedroom home offers 1650 square feet of space and comfortably accommodates up to 7 guests. The home features a fully equipped kitchen, a relaxing Jacuzzi, a private garden with barbecue grills, and stunning mountain views, providing everything you need for a comfortable and enjoyable stay.

Greenwater Pond, MA
06/18 – 06/21
$419/nighttotal: $1257 (3 )
Staycation At Private Lake Cottage Near Jacob’s Pillow And Tanglewood
1 1cottage , Becket
This family-friendly vacation rental is located on a lake in Becket, just two miles from Iroquois Waterfront and October Mountain State Forest and six miles from Becket Land Trust Historic Quarry and Pyramid Lake. The cottage has received excellent ratings for location, cleanliness, and user experience.
The 1510 square foot cottage features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a fireplace, a terrace or balcony, a garden, and parking, allowing for a relaxing and enjoyable stay.
The 1510 square foot cottage features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, a fireplace, a terrace or balcony, a garden, and parking, allowing for a relaxing and enjoyable stay.

Greenwater Pond, MA
06/17 – 06/20
$279/nighttotal: $837 (3 )
Gateway To The Berkshires - Renovated Downtown Apartment
1 2apartment , Lee
This Lee, Massachusetts apartment is conveniently located near the Lee Library, Animagic Museum of Animation, and Berkshire Mountain Country Store, with the Housatonic River and Greenock Country Club a short 15-minute drive away.
This one-bedroom, one-bathroom rental sleeps four guests and features a fully equipped kitchen with a refrigerator, oven, stovetop, microwave, and coffee/tea maker, plus free WiFi and air conditioning.
This one-bedroom, one-bathroom rental sleeps four guests and features a fully equipped kitchen with a refrigerator, oven, stovetop, microwave, and coffee/tea maker, plus free WiFi and air conditioning.

Greenwater Pond, MA
06/17 – 06/20
$382/nighttotal: $1146 (3 )
Misty Pines Cabin | Wood Stove • Sauna
1 2cabin , Monterey
This cabin is situated in Monterey, Massachusetts, offering proximity to Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This 3-bedroom, 3-bathroom lodge accommodates up to 8 guests and features an outdoor wood-fired sauna, a fully equipped kitchen, and a wood-burning stove, with easy access to Butternut Ski Area.
This 3-bedroom, 3-bathroom lodge accommodates up to 8 guests and features an outdoor wood-fired sauna, a fully equipped kitchen, and a wood-burning stove, with easy access to Butternut Ski Area.

Greenwater Pond, MA
06/18 – 06/21
$435/nighttotal: $1305 (3 )
Berkshire 4 Bed Historic Farmhouse Of Sir Kitson
1 1apartment , Tyringham
This Early American Colonial farmhouse sits on a 4-acre estate in the Santarella section of Tyringham, Massachusetts, offering easy access to Berkshire attractions and nearby lakes and hiking trails.
The 4-bedroom, 2-bathroom property sleeps 9 guests and features a renovated kitchen, spacious living room with stone fireplace, game room, gardens, a lily pond, and a fire pit.
The 4-bedroom, 2-bathroom property sleeps 9 guests and features a renovated kitchen, spacious living room with stone fireplace, game room, gardens, a lily pond, and a fire pit.

Greenwater Pond, MA
10/10 – 10/18
$218/nighttotal: $1744 (8 )
A-frame Cabin W/ Furnished Deck In Becket!
2 2cabin , Becket
This Becket, Massachusetts cabin rental boasts a secluded 4-acre wooded setting, a short walk from a community lake and near the Chester-Blandford State Forest.
The two-bedroom, one-bathroom house sleeps six guests comfortably, featuring fireplaces, a modern kitchen with appliances, a smart TV, EV charger, outdoor deck with grill, and pet-friendly accommodations (fee applies).
The two-bedroom, one-bathroom house sleeps six guests comfortably, featuring fireplaces, a modern kitchen with appliances, a smart TV, EV charger, outdoor deck with grill, and pet-friendly accommodations (fee applies).

Greenwater Pond, MA
10/10 – 10/18
$299/nighttotal: $2392 (8 )
Becket Contemporary Cottage In The Woods Overlooking A Private Spring Fed Pond
3 2apartment , Becket
This Becket apartment is located in the Berkshires, overlooking a spring-fed pond and just minutes away from Jacob's Pillow and the Appalachian Trail. The apartment has received excellent ratings for its location, cleanliness, and user experience.
This three-bedroom, three-bathroom home can accommodate up to six guests. The apartment features a private pond, walking trails, a master suite with a Jacuzzi, a guest bedroom with an ensuite bathroom, and a wrap-around deck.
This three-bedroom, three-bathroom home can accommodate up to six guests. The apartment features a private pond, walking trails, a master suite with a Jacuzzi, a guest bedroom with an ensuite bathroom, and a wrap-around deck.












