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

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires, MA
9.7 126 reviews
The Berkshires, MA
11/20 – 11/23
$373/nighttotal: $1119 (3 )

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

4 5
cabin, Sandisfield
This cabin is located in a peaceful and serene area of Sandisfield, within a short distance of Otis Ridge, Ashintully Gardens, and McLennan Reservation. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 1980 square feet and can accommodate up to 10 guests in its 4 bedrooms. It features a spacious garden, a barbecue grill, a cozy fireplace, a fully equipped kitchen, a comfortable sofa bed, a DVD player, a spa, a tennis court, and parking.
Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow - The Berkshires, MA
10 126 reviews
The Berkshires, MA
09/20 – 09/23
$723/nighttotal: $2169 (3 )

Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow

4 2
apartment, Monterey
This family-friendly vacation home is located on a lake in Monterey, within 2 miles of Beartown State Forest and Bidwell House Museum. It has excellent user, location, and cleanliness ratings.
The house has 4 bedrooms and 3100 square feet of floor area. It includes a patio, DVD player, fireplace, kitchen with refrigerator and oven, and a smoke-free environment. Guests can also enjoy a garden with barbecue grills, a fitness center, and parking.
Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington - The Berkshires, MA
10 11 reviews
The Berkshires, MA
08/18 – 08/25
$1247/nighttotal: $8729 (7 )

Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington

5 7
apartment, Monterey
This five-bedroom Monterey vacation home is located near the Bidwell House Museum (1.7 miles) and within six miles of McLennan Reservation, Ashintully Gardens, Dry Hill, and Lake Buel.
This 2450-square-foot house sleeps up to 14 guests and boasts a fully equipped kitchen, a fitness center, a jacuzzi, and a terrace, offering convenient access to Monterey attractions.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.2 11 reviews
The Berkshires, MA
07/10 – 07/11
$1047/nightfor 1 night

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.
Light-filled Gb Oasis, Trails, Lake, Fireplace - The Berkshires, MA
The Berkshires, MA
09/20 – 09/23
$481/nighttotal: $1443 (3 )

Light-filled Gb Oasis, Trails, Lake, Fireplace

3 2
house, Monterey
This vacation home in Great Barrington is 11 miles from the Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club, offering access to trails and a lake.
This 1710 square foot house accommodates up to 15 guests with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, air conditioning, a fireplace, and free private parking.
Forget-me-not By Avantstay - The Berkshires, MA
The Berkshires, MA
08/18 – 08/25
$1545/nighttotal: $10815 (7 )

Forget-me-not By Avantstay

5 7
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.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
8.9 19 reviews
The Berkshires, MA
07/08 – 07/12
$637/nighttotal: $2548 (4 )

Hilltop Escape With Views & Hot Tub

3 4
apartment, New Marlborough
This three-bedroom, two-bathroom Berkshire retreat is situated on 3.5 acres of wooded land near Great Barrington, Massachusetts, a 12-minute drive from town and within easy reach of Stockbridge and Lenox.
This New Marlborough vacation rental boasts a chef's kitchen with high-end appliances, a seven-person hot tub, a gas fireplace, and a media room, comfortably accommodating six guests with stunning mountain views.
Berkshire Treehouse Retreat - The Berkshires, MA
9.8 154 reviews
The Berkshires, MA
07/08 – 07/12
$317/nighttotal: $1268 (4 )

Berkshire Treehouse Retreat

3 4
cabin, New Marlborough
This charming treehouse cabin is located in the woods near Great Barrington, Massachusetts, offering a peaceful escape just a short drive from the town center. The cabin consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The two-level treehouse features a unique design with a live tree running through its interior, accommodating up to 5 guests. Enjoy the outdoors with amenities like a gas grill, a solo stove, and an outdoor dish station, perfect for a glamping experience.
Berkshire Lakefront Lighthouse Getaway - The Berkshires, MA
9.8 73 reviews
The Berkshires, MA
08/08 – 08/10
$434/nighttotal: $868 (2 )

Berkshire Lakefront Lighthouse Getaway

1 2
apartment, Otis
This Otis, Massachusetts lighthouse rental sits on the shores of East Otis Reservoir, offering easy access to Berkshire's fall foliage and water activities.
The 450-square-foot dwelling features one bedroom, one bathroom, sleeps four, includes a kitchen with a fridge and microwave, and boasts an 800-square-foot deck and shared dock for swimming, fishing, and kayaking.
Berkshires Modern Cabin With Babbling Brook - The Berkshires, MA
10 14 reviews
The Berkshires, MA
07/08 – 07/12
$571/nighttotal: $2284 (4 )

Berkshires Modern Cabin With Babbling Brook

3 4
apartment, Sandisfield
The Cabin is a secluded accommodation in Otis, Massachusetts, with a unique location amid a serene forest with a babbling brook and expansive forest views. It has excellent user, location, and cleanliness ratings.
The Cabin has a cozy and modern interior with cream, green, and wood accents, a fully stocked kitchen open to living and dining areas, an outdoor deck with a dining table, patio lights, and BBQ, 3 bedrooms, 2 bathrooms, and a guest capacity of 7. The 24-acre swimming lake, heated outdoor pool, and tennis courts are within a 5-minute walk, and cultural venues like Tanglewood and Jacobs Pillow are nearby.
Contemporary Modern Mountain Retreat - The Berkshires, MA
10 1 review
The Berkshires, MA
09/20 – 09/23
$390/nighttotal: $1170 (3 )

Contemporary Modern Mountain Retreat

1 2
apartment, Monterey
This Monterey home provides a secluded woodland setting with mountain ridge views, situated half a mile from Lake Garfield and its hiking trails, and a 10-minute drive to Great Barrington for skiing, dining, and shopping. This 4-bedroom, 3-bathroom house accommodates up to 10 guests and features a fully equipped kitchen, air conditioning, a screened-in porch, a spacious deck with a fire pit, and a primary king bedroom with an ensuite jacuzzi tub.
The Owl And Firefly – A Cabin For Families - The Berkshires, MA
10 6 reviews
The Berkshires, MA
11/20 – 11/23
$438/nighttotal: $1314 (3 )

The Owl And Firefly – A Cabin For Families

1 5
apartment, Otis
This apartment in Otis offers a secluded woodland escape, nestled deep within the pine forests and stone walls of the southern Berkshires, providing 6 acres of private property.
This 3-bedroom, 3-bathroom cabin accommodates up to 10 guests with 7 beds, featuring a fully equipped kitchen, an indoor climbing wall, a record player, and a 65" Roku TV, with two pack-n-play cribs available.

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.

Serene Berkshires Home On 5+ Acres, Rustic & Chic - The Berkshires, MA
9.5 70 reviews
The Berkshires, MA
07/16 – 07/18
$1009/nighttotal: $2018 (2 )

Serene Berkshires Home On 5+ Acres, Rustic & Chic

5 2
apartment, Otis
Otis apartment is a spacious retreat nestled in the heart of the Berkshires, offering a secluded sanctuary surrounded by breathtaking natural beauty. This highly-rated apartment features five bedrooms, three bathrooms, and dedicated spaces for every need, ensuring comfort and privacy for up to 10 guests.
With its exquisite artwork and furnishings by local Berkshires artists, this apartment creates a warm and inviting atmosphere that celebrates the region's creative spirit. Guests can enjoy a variety of entertainment options, including a game room with shuffleboard and arcade games, a home gym, and a screened porch with picturesque views. The outdoor dining area, fire pit, and games allow guests to fully embrace the beauty of the Berkshires while enjoying the fresh mountain air.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.5 62 reviews
The Berkshires, MA
09/20 – 09/23
$1083/nighttotal: $3249 (3 )

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 2
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.
Lakefront Berkshire Retreat! - The Berkshires, MA
10 40 reviews
The Berkshires, MA
07/08 – 07/12
$581/nighttotal: $2324 (4 )

Lakefront Berkshire Retreat!

1 4
apartment, Becket
This Becket, Massachusetts waterfront rental boasts three bedrooms, one bathroom, and sleeps six, offering stunning lake views and proximity to Jacob's Pillow (5 minutes), Becket State Forest (5 minutes), and Lee Premium Outlets (15 minutes).
The open-concept home features a fully equipped kitchen with dishwasher, air conditioning, a large deck perfect for BBQs, and access to kayaks, a paddleboat, and other seasonal water activities.
Sleek Butternut Ski Chalet Lakefront Hottub Sauna - The Berkshires, MA
9.8 13 reviews
The Berkshires, MA
07/08 – 07/12
$1099/nighttotal: $4396 (4 )

Sleek Butternut Ski Chalet Lakefront Hottub Sauna

1 4
chalet, Monterey
This luxurious 5-bedroom, 4-bathroom chalet is located on Lake Garfield in the Berkshires, a 7-minute drive from Butternut Ski Resort and a 15-minute drive from Catamount Ski Resort, offering easy access to Great Barrington.
This spacious home comfortably sleeps 14 guests and boasts a chef's kitchen, two living rooms, a year-round hot tub, a fire pit, two decks, and access to kayaks and paddleboards in the summer, making it perfect for family vacations or group getaways near Monterey.

Best The Berkshires, MA accommodation with a fireplace

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits! - The Berkshires, MA
10 8 reviews
The Berkshires, MA
07/08 – 07/12
$470/nighttotal: $1880 (4 )

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

3 4
apartment, Monterey
This Monterey mountain home is located 0.4 miles from Lake Buel and within 3 miles of Dry Hill and Les Trois Emme Winery, offering easy access to outdoor recreation and wine tasting.
This three-bedroom, one-bathroom vacation rental sleeps six, features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, a patio, free WiFi, and a fireplace.
Lakeside Berkshires Chalet | Sauna & Fireplace - The Berkshires, MA
The Berkshires, MA
11/20 – 11/23
$466/nighttotal: $1398 (3 )

Lakeside Berkshires Chalet | Sauna & Fireplace

3 5
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.
Iconic Lodge In The Berkshires - The Berkshires, MA
9.7 61 reviews
The Berkshires, MA
09/20 – 09/23
$1273/nighttotal: $3819 (3 )

Iconic Lodge In The Berkshires

4 2
cabin, Sandisfield
This Sandisfield cabin is located in the Berkshires, a scenic region of western Massachusetts, just a short drive from popular destinations like Stockbridge, Great Barrington, and Tanglewood. The cabin has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travelers seeking a comfortable and enjoyable stay.
This charming home features four bedrooms, two lofts, and a spacious layout, accommodating up to 12 guests. Amenities include a massive stone fireplace, a modern kitchen, a billiards lounge, an indoor swimming pool, a yoga room, and a private setting with ample parking.
Direct To Lake Garfield: Summer Dates Available! - The Berkshires, MA
9.9 22 reviews
The Berkshires, MA
11/13 – 11/16
$485/nighttotal: $1455 (3 )

Direct To Lake Garfield: Summer Dates Available!

3 5
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.

Frequently Asked Questions about accommodations in The Berkshires, MA

Destinations nearby

Best The Berkshires, MA accommodation with a balcony

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
11/13 – 11/16
$1382/nighttotal: $4146 (3 )

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

4 5
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.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
The Berkshires, MA
07/08 – 07/12
$822/nighttotal: $3288 (4 )

Hilltop Escape With Views & Hot Tub

3 4
house, New Marlborough
This hilltop house in New Marlborough offers expansive views and is located 10 miles from Great Falls and the Canaan Village Historic District, with Haystack Mountain State Park 11 miles away and the Norman Rockwell Museum and Tanglewood Musical Center within a 20-mile radius.
This 2370 square foot residence accommodates up to 11 guests with 3 bedrooms, 3 bathrooms, air conditioning, a Jacuzzi, a full kitchen, and a terrace, all featuring free private parking.
Lakeside Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews
The Berkshires, MA
07/08 – 07/12
$851/nighttotal: $3404 (4 )

Lakeside Retreat | Dock, Kayaks & Fire Pit

3 4
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.
Beautiful Berkshire Family Home - The Berkshires, MA
9.4 3 reviews
The Berkshires, MA
09/20 – 09/23
$642/nighttotal: $1926 (3 )

Beautiful Berkshire Family Home

5 2
apartment, Monterey
This secluded 2500 sq ft post and beam house in Monterey offers a private woodland setting, just 5 minutes from the village and lake, and 12-15 miles from Butternut Skiing and the Appalachian Trail.
This family-friendly 5-bedroom, 3-bathroom lodge accommodates up to 12 guests with amenities including a cathedral living room, wood-burning stove, full kitchen with Whirlpool fridge and Bosch dishwasher, a separate family room, and outdoor dining options, with pets welcome.

Best The Berkshires, MA accommodation with a kitchen

Peaceful, Post And Beam Loft, Sleeps 9 - The Berkshires, MA
9.7 116 reviews
The Berkshires, MA
07/08 – 07/12
$301/nighttotal: $1204 (4 )

Peaceful, Post And Beam Loft, Sleeps 9

1 4
apartment, New Marlborough
This New Marlborough apartment is a short drive from popular Berkshire attractions like Ski Butternut, Dry Hill, and Tanglewood, offering a tranquil setting for a relaxing getaway. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartment features a spacious living area, a well-equipped kitchen, and comfortable sleeping arrangements for up to nine guests, including a private bedroom, a loft, and a queen-size air bed. Guests can enjoy amenities like a washer and dryer, parking for six, and a luxurious bathroom with a double-headed shower and a two-person Jacuzzi tub.
Cozy Cabin Retreat In The Berkshires - The Berkshires, MA
8.7 14 reviews
The Berkshires, MA
07/24 – 07/26
$381/nighttotal: $762 (2 )

Cozy Cabin Retreat In The Berkshires

1 4
cabin, Otis
This beautiful two-bedroom cabin is situated in the Berkshires at Big Pond in Otis, Massachusetts. It is within walking distance of the lake and close to local restaurants and shops. The cabin is located in a peaceful and secluded area, yet it is within driving distance of several major tourist attractions in Otis, including the Norman Rockwell Museum (10 miles) and the Otis Reservoir (5 miles).
The cabin has a user rating of "very good" and a location rating of "very good". It has two bedrooms, one bathroom, and a guest capacity of 8. The cabin has a fully equipped kitchen, a dining room, and a living room. It also has a stone fireplace and is decorated in a rustic style.
Scribe's Stable | A/c • Screened Porch • Sleeps 6 - The Berkshires, MA
9.9 57 reviews
The Berkshires, MA
07/08 – 07/12
$332/nighttotal: $1328 (4 )

Scribe's Stable | A/c • Screened Porch • Sleeps 6

1 4
farm, Monterey
This Monterey County renovated barn, perfect for a Monterey getaway, offers a 2-bedroom, 1-bathroom rental sleeping up to 6 guests with a small kitchenette, private patio, and Wi-Fi.
The property features an open layout with vaulted ceilings and exposed beams, plus amenities including parking, a garden, and pet-friendliness, making it ideal for exploring the Monterey Peninsula.
Little Longbow Lakefront Chalet - The Berkshires, MA
9.8 26 reviews
The Berkshires, MA
09/20 – 09/23
$684/nighttotal: $2052 (3 )

Little Longbow Lakefront Chalet

2 2
chalet, Becket
This Becket waterfront cabin is located within two miles of Pyramid Lake, Jacob's Pillow Dance Festival, and October Mountain State Forest, offering easy access to swimming, boating, hiking, and world-class dance performances.
The 2-bedroom, 2-bathroom house sleeps five, features a private garden, terrace, spa, and on-site barbecue grills, plus amenities like air conditioning, internet, and a fully equipped kitchen including a microwave and refrigerator.
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