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The Berkshires, MA accommodations
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4010 Lodgings in The Berkshires, MA

Best family friendly The Berkshires, MA lodging

Among the 4010 accommodations in The Berkshires, MA, here are the 4 best for families

Berkshire Retreat At Cantina 229 - The Berkshires, MA
10 18 reviews

Berkshire Retreat At Cantina 229

apartment, New Marlborough
This five-bedroom, three-bathroom house in New Marlborough, Berkshire, is situated on a five-acre plot, 24km from Great Barrington town centre.
The 2,584 sq ft property boasts a spacious layout sleeping up to 10 guests, offering a fully equipped kitchen, games room, and outdoor fire pit, with convenient parking and proximity to hiking and skiing in the Berkshires.
Light-filled Cottage - The Berkshires, MA
10 4 reviews

Light-filled Cottage

apartment, New Marlborough
This four-bedroom New Marlborough cottage, perfect for families, is situated in a secluded woodland setting near numerous lakes and waterfalls, offering easy access to local cafes and restaurants.
The self-catering property sleeps five, features a wood-burning stove, high-speed internet, a garden, and a fitness centre, and provides DVDs, books, and a sound system for guest entertainment.
Lake Front Retreat - Stylish Berkshire  Home - The Berkshires, MA
9.8 177 reviews

Lake Front Retreat - Stylish Berkshire Home

apartment, Becket
This renovated mid-century home is located on Long Bow Lake, a peaceful lake just 32 kilometres from Downtown Lee, with shops, hiking trails and the Otis Ridge ski area nearby. The property has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
This spacious split-level house sleeps six guests and includes four bedrooms and two bathrooms. The home has a fully equipped kitchen, a garden, a tennis court, a private dock, kayaks, a ping pong table, a Weber gas grill, and a screened-in porch, perfect for enjoying the beautiful scenery and outdoor activities.
Sunny Oasis In The Woods In Otis - The Berkshires, MA
10 15 reviews

Sunny Oasis In The Woods In Otis

apartment, Otis
This Berkshire County house, less than 1.6km from Route 23, offers easy access to Stockbridge, Great Barrington, and Lenox, placing guests near popular Berkshire attractions such as Tanglewood and Jacob's Pillow.
The three-bedroom, two-bathroom property sleeps six, boasting a contemporary open-plan living area, a first-floor den, and outdoor amenities including two kayaks and a mini frisbee golf course; all within a secluded wooded setting.

Best The Berkshires, MA accommodation with a fireplace

Hilltop Escape With Views & Hot Tub - The Berkshires, MA
9.2 24 reviews

Hilltop Escape With Views & Hot Tub

apartment, New Marlborough
This three-bedroom, two-bathroom Berkshire retreat is situated on a 1.4 hectare wooded plot near Great Barrington, Massachusetts, a 19km drive from its town centre and within 32-40km of Stockbridge and Lenox.
The property, sleeping six guests, boasts a chef's kitchen, jacuzzi, garden, parking, and a media room that doubles as a third sleeping area; nearby attractions include Tanglewood, Butternut Ski Resort, and Lake Buel.
Berkshire Wonderland Family Home 7 Acr Lake Access - The Berkshires, MA
9.9 81 reviews

Berkshire Wonderland Family Home 7 Acr Lake Access

apartment, Otis
This 4-bedroom apartment is situated in the Berkshire countryside, just 10km from a local lake and a short drive from Great Barrington and ski resorts. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a spacious and open layout, comfortably accommodating up to 11 guests. It includes a well-equipped kitchen, a cosy living room, a den with a TV, a library, and a wrap-around porch. Guests can enjoy access to the lake for swimming and fishing, as well as a canoe and kayak.
Lakefront Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews

Lakefront Retreat | Dock, Kayaks & Fire Pit

apartment, Becket
This lakeside chalet in Becket, Massachusetts is located just 8 kilometres from Jacob's Pillow, 40 kilometres from Tanglewood and 48 kilometres from Butternut ski resort.
The three-bedroom bungalow offers space for six guests and features a private dock, kayaks, a garden, parking, a terrace, a fully equipped kitchen and air conditioning.
Bosworth Tap Room - The Berkshires, MA
9.9 100 reviews

Bosworth Tap Room

apartment, Sandisfield
This historic house is located in the southeast corner of the Berkshires, around 48 kilometres from the nearest shopping centre, offering a peaceful retreat in the beautiful countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The house has four bedrooms and one bathroom, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a garden, and air conditioning, alongside modern amenities while retaining its authentic colonial charm.

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Best The Berkshires, MA accommodation with a balcony

Treetop Hideaway In Tyringham - The Berkshires, MA
9.2 11 reviews

Treetop Hideaway In Tyringham

apartment, Tyringham
This log cabin, nestled in the district of Monterey bordering Tyringham, is located within a short drive of attractions like Greenock Country Club, Otis Ridge, Ashintully Gardens, and Berkshire Scenic Railway Museum. This secluded dwelling, situated on 35+ acres of woodland, offers a peaceful retreat with stunning views of the Tyringham Valley, a spacious living area with vaulted ceilings and a fireplace, a modern kitchen, a screen porch with a hot tub, and a wraparound deck.
Forest Hollow | Waterfront  Kayaks  Wood Stove - The Berkshires, MA
9.4 11 reviews

Forest Hollow | Waterfront Kayaks Wood Stove

apartment, Monterey
This three-bedroom lakefront property in Monterey, Massachusetts, within the Berkshires, offers direct access to Lake Garfield, with two docks and kayaks, and is approximately 0.8 km from the Bidwell House Museum and the Mahaiwe Performing Arts Centre.
The 185 square metre house features a cosy open-plan living area with a fireplace, a downstairs den/games room, a spacious deck, parking for three cars, and sleeps up to six guests, including children accommodated in trundle beds.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey
This luxurious four-bedroom lakeside property near Lake Garfield in the Berkshires offers uninterrupted views and is within driving distance of attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort.
Sleeping up to twelve guests, this three-story house boasts a fully equipped kitchen, a second kitchenette, hot tub, sauna, and access to a seasonal dock, alongside various indoor games including ping pong and pool, making it ideal for families or large groups.
Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires, MA
10 1 review

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
This lakeside property in Monterey, Massachusetts, offers a private dock on Lake Garfield, convenient access to Otis Ridge, Les Trois Emme Winery, McLennan Reservation, and Dry Hill (distances unspecified).
The 375 square metre (approximately 4030 square feet) dwelling comprises a spacious main house with a basement TV room, a separate guest house with a wood stove sleeping two, four bedrooms, three bathrooms, and can accommodate up to ten guests, benefiting from a garden, terrace, parking, internet access, and a fully equipped kitchen including a fridge, microwave, and dishwasher.

Best The Berkshires, MA accommodation with a kitchen

All-season Berkshires Escape: Ski, Hike, Swim - The Berkshires, MA
10 8 reviews

All-season Berkshires Escape: Ski, Hike, Swim

apartment, New Marlborough
This New Marlborough property offers a tranquil escape along the Konkapot River, bordering protected land and the Beartown State Forest, and is situated less than 8 kilometres from Gedney Farm, Lake Garfield Beach, and Butternut Ski Area.
This spacious four-bedroom holiday home accommodates up to eight guests with its open-plan living area, modern farmhouse decor, and a fully equipped kitchen, complemented by an outdoor entertainment space featuring a balcony, deck, gas grill, and ample seating, ideal for exploring the nearby Appalachian Trail.
Cozy Escape In The Trees Of The Berkshires - The Berkshires, MA
9.5 23 reviews

Cozy Escape In The Trees Of The Berkshires

apartment, New Marlborough
This five-bedroom apartment is situated in New Marlborough, a short drive from scenic hiking trails, swimming lakes, and winter skiing. It has received excellent ratings for user experience, location, and cleanliness.
The apartment has two bathrooms and can comfortably accommodate up to ten guests. It features a fully equipped kitchen, a garden, parking, internet access, and a range of amenities for both indoor and outdoor relaxation, including a fireplace, a porch, a trampoline, a tire swing, and a soccer net.
Steepletop - Nature Lovers Paradise With Rec Room - The Berkshires, MA
8.8 15 reviews

Steepletop - Nature Lovers Paradise With Rec Room

apartment, New Marlborough
Steepletop Lodge is a woodland retreat in New Marlborough, Massachusetts, a short drive from the Berkshires and an hour from Springfield. It has excellent user, location, and cleanliness ratings.
The lodge has four bedrooms and two bathrooms, accommodating up to eight guests. It offers a range of amenities, including a fully equipped kitchen, a screened porch with a fireplace, a private balcony, a fitness area, a dedicated workspace, and a dining table crafted from a repurposed bowling lane.
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires, MA
9.6 134 reviews

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

cabin, Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
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