
Lake Onota, MA
06/20 – 07/02
$429/nighttotal: $5148 (12 )
Cozy Home In Lenox
2 2apartment , Lenox
This Lenox house rental sleeps three guests in two bedrooms and one bathroom, offering a smoke-free environment ideal for allergy sufferers.
The property includes a fully equipped kitchen with refrigerator, microwave, oven, and stovetop, in-unit laundry, a smart TV, coffee/tea maker, and housekeeping is available upon request; further details on the precise location within Lenox and proximity to attractions are needed.
The property includes a fully equipped kitchen with refrigerator, microwave, oven, and stovetop, in-unit laundry, a smart TV, coffee/tea maker, and housekeeping is available upon request; further details on the precise location within Lenox and proximity to attractions are needed.

Lake Onota, MA
10/15 – 10/25
$208/nighttotal: $2080 (10 )
Charming Historic Cottage On Scenic Road To Mt. Greylock
2 2cottage , Lanesborough
This Lanesborough cottage is located in the mountains, just a mile from Mount Greylock State Reservation and within 3 miles of both the Mount Greylock State Reservation Visitor Center and Jiminy Peak Mountain Resort. The 1,600 square foot cottage features two bedrooms, one bathroom, and can accommodate up to five guests, offering modern amenities like free WiFi, a DVD player, and a fully equipped kitchen.

Lake Onota, MA
08/22 – 09/03
$351/nighttotal: $4212 (12 )
Stone School Cottage
1 4apartment , Lanesborough
This Lanesborough studio, located on the scenic road to Mount Greylock midway between Williamstown and Lenox, is a former one-room schoolhouse dating back to 1832.
The two-bedroom studio, perfect for families or groups of up to five, features a large loft space with a queen bed, daybed, floor mattresses, and a sitting/dining area, plus amenities like air conditioning, a Keurig coffee maker, and a TV with streaming services.
The two-bedroom studio, perfect for families or groups of up to five, features a large loft space with a queen bed, daybed, floor mattresses, and a sitting/dining area, plus amenities like air conditioning, a Keurig coffee maker, and a TV with streaming services.

Lake Onota, MA
08/22 – 09/03
$418/nighttotal: $5016 (12 )
Berkshire's Sweet Spot 2-pool And Spa
3 4apartment , Pittsfield
This Pittsfield duplex is conveniently located in central Berkshire County, within walking distance of downtown Pittsfield, Tanglewood, and the Mahaiwe Performing Arts Center. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The home features three bedrooms and a queen-sized sofa bed, comfortably sleeping up to eight guests. Enjoy a private backyard with a seasonal pool, a year-round hot tub, a fully equipped kitchen, and modern amenities like smart TVs.
The home features three bedrooms and a queen-sized sofa bed, comfortably sleeping up to eight guests. Enjoy a private backyard with a seasonal pool, a year-round hot tub, a fully equipped kitchen, and modern amenities like smart TVs.

Lake Onota, MA
08/22 – 09/03
$694/nighttotal: $8328 (12 )
Berkshires Chalet Mins To Tanglewood/lenox
1 4apartment , Richmond
This Richmond rental is located approximately 4 miles from Tanglewood and offers convenient access to Berkshire attractions, including skiing, swimming, boating, hiking, summer theater, and dining. This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a new kitchen with stainless steel appliances, a screened porch, central air conditioning, and a covered outdoor hot tub.

Lake Onota, MA
08/22 – 09/03
$374/nighttotal: $4488 (12 )
3 Bedroom , 2 Bath, Beautifully Appointed Home
1 4apartment , Pittsfield
This Pittsfield home is conveniently located near popular attractions like Tanglewood, the Norman Rockwell Museum, and Mass MOCA, making it a great base for exploring the city. The home has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and a fitness center, ensuring a comfortable and enjoyable stay.
This 3-bedroom, 2-bathroom house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and a fitness center, ensuring a comfortable and enjoyable stay.

Lake Onota, MA
08/22 – 09/03
$424/nighttotal: $5088 (12 )
Friendly Hills | Passive Home Ev Charger
3 4apartment , Hancock
This mid-century modern vacation rental in Pittsfield, near Hancock Shaker Village, offers easy access to Pittsfield attractions like Bousquet Ski Area and the Berkshire Museum.
The three-bedroom, two-bathroom home features a fully equipped kitchen with a fridge, microwave, and dishwasher; high-speed Wi-Fi; air conditioning; and parking, all within a unique design inspired by Frank Lloyd Wright on six private acres with hiking trails and ponds.
The three-bedroom, two-bathroom home features a fully equipped kitchen with a fridge, microwave, and dishwasher; high-speed Wi-Fi; air conditioning; and parking, all within a unique design inspired by Frank Lloyd Wright on six private acres with hiking trails and ponds.

Lake Onota, MA
08/22 – 09/03
$134/nighttotal: $1608 (12 )
Heart Of The Berkshires
1 4apartment , Pittsfield
This Pittsfield apartment is conveniently located in a safe neighborhood, just a short walk from a bakery, coffee shop, and other amenities and approximately 2 miles from the site that inspired Herman Melville's "Moby Dick." The apartment consistently receives excellent ratings for cleanliness, location, and overall user experience.
The apartment has 3 bedrooms and 1 bathroom, comfortably accommodating up to 5 guests. Enjoy a fully equipped kitchen, allergy-friendly features, private access, a shared deck with a grill, DirectTV, ample off-street parking, and easy access to various attractions like Tanglewood, Berkshire Theatre, and Jiminy Peak.
The apartment has 3 bedrooms and 1 bathroom, comfortably accommodating up to 5 guests. Enjoy a fully equipped kitchen, allergy-friendly features, private access, a shared deck with a grill, DirectTV, ample off-street parking, and easy access to various attractions like Tanglewood, Berkshire Theatre, and Jiminy Peak.

Lake Onota, MA
10/15 – 10/25
$169/nighttotal: $1690 (10 )
Spacious 2 Bedroom Downtown Very Nice Area!
1 2apartment , Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.

Lake Onota, MA
10/15 – 10/25
$300/nighttotal: $3000 (10 )
Cantabile Life In The Berkshires
1 2apartment , Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.

Lake Onota, MA
08/22 – 09/03
$630/nighttotal: $7560 (12 )
The Oliver Wendell Holmes Guesthouse @ Holmesdale
1 4apartment , Pittsfield
Historic Holmesdale Cottage is situated on 16 acres of a private estate on the Pittsfield/Lenox border, offering tranquility amidst the Berkshires. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom cottage accommodates up to four guests, featuring a king-size bed and a spiral staircase.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.

Lake Onota, MA
10/15 – 10/25
$261/nighttotal: $2610 (10 )
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
2 2farm , Lenox
This Lenox, Massachusetts farmhouse rental is located on a mountainside, within 2 miles of the Housatonic River, Arrowhead, and the Arrowhead Museum.
This 2-bedroom, 1-bathroom vacation home sleeps 6, features a garden, air conditioning, Wi-Fi, and a kitchen with a refrigerator and microwave; nearby attractions include Guido's Marketplace and the Pleasant Valley Wilderness Sanctuary.
This 2-bedroom, 1-bathroom vacation home sleeps 6, features a garden, air conditioning, Wi-Fi, and a kitchen with a refrigerator and microwave; nearby attractions include Guido's Marketplace and the Pleasant Valley Wilderness Sanctuary.













