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The Berkshires, MA accommodations
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2574 Lodgings in The Berkshires, MA

Popular Family Lodgings in The Berkshires, MA

These family-friendly lodgings in The Berkshires, MA offer plenty of room with trails and fresh air right outside your door.

Berkshires Cedar Cabin/4 Acres Woods/private Idyll - The Berkshires, MA
10 6 reviews
The Berkshires, MA
08/26 – 09/02
$266/nighttotal: $1862 (7 )

Berkshires Cedar Cabin/4 Acres Woods/private Idyll

1 1
cabin , Otis
This cedar lodge is situated on four private acres in the Berkshires, a short distance from Otis Reservoir, hiking trails, ski resorts, organic farms, Jacob's Pillow, and Tanglewood.
This family-friendly, pet-friendly cabin accommodates up to six guests with three bedrooms, two bathrooms, air conditioning on both floors, a well-stocked kitchen, and a sunroom featuring an electric fireplace, offering a tranquil natural escape with immersive forest views.
Berkshire Lakefront Cabin With Modern Luxuries - The Berkshires, MA
10 78 reviews
The Berkshires, MA
08/31 – 09/03
$627/nighttotal: $1881 (3 )

Berkshire Lakefront Cabin With Modern Luxuries

1 2
apartment , Otis
This newly renovated lakefront cabin is located on Massachusetts' largest recreational lake, just a 25-minute drive from major Berkshire attractions. The cottage has received excellent ratings for its cleanliness, location, and overall user experience.
The cabin offers a unique layout with a separate studio/office space, ideal for families or groups of up to six guests. Enjoy the lakefront location with its stunning sunset views, private hot tub, and access to kayaks, docks, and state forest trails.
The Owl And Firefly  A Cabin For Families - The Berkshires, MA
10 1 review
The Berkshires, MA
08/26 – 09/02
$687/nighttotal: $4809 (7 )

The Owl And Firefly A Cabin For Families

3 1
apartment , Otis
This Otis cabin, set among pines and stone walls, is located a short drive from the Appalachian Trail and Otis Reservoir, offering a secluded experience with proximity to Hayes Pond (10560 feet) and Otis Reservoir (13 minutes).
This 1920 sq ft, 3-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and internet, ideal for families seeking outdoor activities and après-ski relaxation near Jacob's Pillow and Bidwell House Museum.
Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires! - The Berkshires, MA
10 5 reviews
The Berkshires, MA
10/23 – 10/25
$332/nighttotal: $664 (2 )

Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires!

2 2
apartment , Becket
This dog-friendly A-frame rental in Sherwood Forest, Becket, offers easy access to a lake with beach access and is close to the Bidwell House Museum and Berkshire Theatre Festival.
The two-bedroom, one-bathroom home sleeps four and includes a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, and a garden; guests can enjoy on-site spa facilities and parking.

Best The Berkshires, MA accommodation with a fireplace

Massachusetts Lake House W/ Dock - Pets Welcome! - The Berkshires, MA
9.2 38 reviews
The Berkshires, MA
10/23 – 10/25
$819/nighttotal: $1638 (2 )

Massachusetts Lake House W/ Dock - Pets Welcome!

4 2
house , New Marlborough
This renovated lakefront home in New Marlborough is conveniently located just 16 miles from both Cranwell Spa & Golf Club and Tanglewood Musical Center, offering easy access to popular attractions. The house consistently receives excellent user ratings for its location, cleanliness, and overall experience.
The 1400 square foot house comfortably sleeps up to 8 guests in its 4 bedrooms. Guests can enjoy a fully equipped kitchen, air conditioning, a balcony with lake views, a fitness center, a garden, and a private dock for swimming, fishing, or relaxing by the water.
Picturesque Cottage House With Nearby Lake And Cafe - The Berkshires, MA
The Berkshires, MA
09/22 – 09/25
$374/nighttotal: $1122 (3 )

Picturesque Cottage House With Nearby Lake And Cafe

2 2
apartment , New Marlborough
This New Marlborough rental house is located 17 miles from Haystack Mountain State Park and 13 miles from Lake Buel, offering convenient access to natural attractions like Cookson State Forest and Campbell Falls State Park, as well as cultural sites such as Infinity Music Hall and Bistro and Bidwell House Museum.
This 1500 square foot apartment accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen with a dishwasher and oven, a fireplace, a barbecue, an in-unit washer and dryer, and on-site parking.
Forget-me-not By Avantstay - The Berkshires, MA
The Berkshires, MA
08/26 – 09/02
$1451/nighttotal: $10157 (7 )

Forget-me-not By Avantstay

5 1
house , Monterey
This Monterey vacation rental is located 14 miles from Cranwell Spa & Golf Club and 15 miles from the Norman Rockwell Museum, offering easy access to area attractions. The home provides a peaceful retreat in a tranquil setting.
The house has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a fireplace, a jacuzzi, and a lakefront location.
The Lake House - The Berkshires, MA
9.9 35 reviews
The Berkshires, MA
08/31 – 09/03
$362/nighttotal: $1086 (3 )

The Lake House

1 2
apartment , Sandisfield
This Sandisfield-area lake house rental in Otis, MA, offers a peaceful lakeside setting a short walk from a lake perfect for swimming and boating.
The three-bedroom, one-bathroom home comfortably sleeps six guests and includes a fireplace, fire pit, pet-friendly environment, self check-in, and parking for two vehicles.

Frequently Asked Questions about accommodations in The Berkshires, MA

Destinations nearby

Best The Berkshires, MA accommodation with a balcony

Lakeside Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews
The Berkshires, MA
08/26 – 09/02
$686/nighttotal: $4802 (7 )

Lakeside Retreat | Dock, Kayaks & Fire Pit

3 1
apartment , Becket
This lakeside chalet rental in Becket, Massachusetts, is located near Long Bow Lake, five minutes from Jacob's Pillow Dance Festival, 25 minutes from Tanglewood, and 30 minutes from Butternut Ski Area.
The three-bedroom, two-bathroom home offers guests a private dock, kayaks, a deck with a grill, a breakfast/work nook, and a ping pong table, comfortably accommodating up to six people.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.2 11 reviews
The Berkshires, MA
08/14 – 08/17
$831/nighttotal: $2493 (3 )

Treetop Hideaway In Tyringham

4 2
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.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
08/26 – 09/02
$1464/nighttotal: $10248 (7 )

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay

4 1
apartment , Monterey
This Monterey apartment is a Berkshires retreat located on the shores of Lake Garfield, offering stunning lake views and easy access to the region's natural beauty and cultural attractions. The property has earned a very good user rating, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
The home has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities, including a private hot tub, sauna, tennis court, and access to the lake for swimming, fishing, and kayaking.
Lakeside Berkshires Chalet | Sauna & Fireplace - The Berkshires, MA
The Berkshires, MA
08/26 – 09/02
$409/nighttotal: $2863 (7 )

Lakeside Berkshires Chalet | Sauna & Fireplace

3 1
apartment , Becket
This Becket chalet offers a private waterfront location on motorboat-free Longbow Lake, just minutes from Jacob's Pillow and a 25-mile drive to Tanglewood.
This 1390 sq ft residence accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring a wood-burning fireplace, a spacious deck, on-site sauna, and direct dock access for lake activities.

Best The Berkshires, MA accommodation with a kitchen

353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.5 62 reviews
The Berkshires, MA
08/26 – 09/02
$1381/nighttotal: $9667 (7 )

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 1
house , Monterey
This luxurious lakefront home in the Berkshires offers stunning, uninterrupted views of Lake Garfield and is conveniently located near attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort, though precise distances aren't specified.
The four-bedroom, four-bathroom residence sleeps up to twelve guests and boasts a spacious layout including a main living area, a second living room with kitchenette, a sunroom, and a large deck with a BBQ grill; amenities include a swimming pool, hot tub, sauna, and various games.
Private Mountain Retreat - 5 Acres Close To Lakes - The Berkshires, MA
10 14 reviews
The Berkshires, MA
08/14 – 08/17
$674/nighttotal: $2022 (3 )

Private Mountain Retreat - 5 Acres Close To Lakes

1 2
apartment , Otis
This Berkshire County rental is located near the Monterey/Tyringham town line, a 15-20 minute drive from Great Barrington, Lenox, and Tanglewood.
This four-bedroom, three-bathroom Otis apartment sleeps eight guests, boasting a spacious, newly renovated layout with a fully equipped kitchen, luxurious bathrooms, and ample indoor/outdoor space.
Charming Cottage W/ Gorgeous Views. - The Berkshires, MA
9.9 362 reviews
The Berkshires, MA
09/22 – 09/25
$206/nighttotal: $618 (3 )

Charming Cottage W/ Gorgeous Views.

1 2
apartment , Monterey
This accommodation is a private cottage in Monterey, overlooking Lake Garfield and the Berkshire Hills. It is close to summer Arts venues and cultural attractions, and has excellent user, location, and cleanliness ratings.
The cottage has 2 bedrooms, 2 bathrooms, and can accommodate 4 guests. It has a fully equipped kitchen, air conditioning, a garden, and parking. Guests can enjoy stunning views, a serene and private setting, outdoor amenities, high-speed internet, and seasonal activities.
Cozy Berkshire Cottage - The Berkshires, MA
10 1 review
The Berkshires, MA
08/31 – 09/03
$334/nighttotal: $1002 (3 )

Cozy Berkshire Cottage

1 2
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.
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