Places to stay in The Berkshires, MA

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The Berkshires, MA place to stay
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4010 Best places to stay 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

Converted Berkshire Schoolhouse On A Quiet River - The Berkshires, MA
9.9 172 reviews

Converted Berkshire Schoolhouse On A Quiet River

apartment, New Marlborough
This charming cottage is located in the Berkshires, just a short distance from the Butternut ski resort and the town of Great Barrington, offering easy access to both outdoor adventures and cultural attractions. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage features three bedrooms, comfortably accommodating up to five guests. Enjoy a fully equipped kitchen, a spacious garden, a private terrace, and a host of amenities including a BBQ, a coffee grinder, a DVD collection, and a unique "sign the walls" tradition in the bathroom.
East Otis Reservoir Cabin W/ Porch - Walk To Lake! - The Berkshires, MA
9.0 23 reviews

East Otis Reservoir Cabin W/ Porch - Walk To Lake!

cabin, Otis
The East Otis Reservoir Cabin with Porch - Walk to Lake! is located in East Otis, just a short walk from the reservoir and within a 25-mile radius of attractions like Cranwell Spa & Golf Club, Tanglewood, and Norman Rockwell Museum. This charming dwelling has received very good user ratings and excellent scores for location and cleanliness.
The cabin is a comfortable 67 square metres with two bedrooms and one bathroom, sleeping up to four guests. It offers a fully equipped kitchen with a fridge and microwave, air conditioning, a terrace, a garden, parking, and direct access to the reservoir for swimming, fishing, and kayaking.
Berkshires Modern Cabin With Babbling Brook - The Berkshires, MA
10 14 reviews

Berkshires Modern Cabin With Babbling Brook

apartment, Sandisfield
The Cabin is located in the Berkshires, a short walk from a community lake and amenities, and a short drive (around 10km) to popular ski resorts like Otis Ridge and Ski Butternut. It has received excellent ratings for location, cleanliness and overall user experience.
The accommodation has a spacious and open floor plan, ideal for families, and can comfortably sleep up to 7 guests. It offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a wood-burning stove, and a dedicated kids' play area, as well as easy access to hiking trails, cultural attractions, and winter sports.
Beautiful, Private Berkshires Retreat W Magic View! 5min To Lake Garfield Beach - The Berkshires, MA
9.8 149 reviews

Beautiful, Private Berkshires Retreat W Magic View! 5min To Lake Garfield Beach

chalet, Monterey
This spacious apartment, perfect for families and groups, is located in the picturesque Berkshires, within easy reach of popular attractions like Ski Butternut and Great Barrington. The accommodation has consistently received excellent ratings for its cleanliness, location and overall experience.
The apartment is spread over 167 square metres and comfortably sleeps eight guests, featuring three bedrooms and two bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a fitness centre, Wi-Fi, and parking.

Best The Berkshires, MA accommodations with a fireplace

Direct To Lake Garfield: Summer Dates Available! - The Berkshires, MA
No reviews

Direct To Lake Garfield: Summer Dates Available!

apartment, Monterey
This waterfront holiday home in Monterey offers direct access to Lake Garfield, with Ski Butternut less than 10 kilometres away and Great Barrington approximately 15 kilometres distant.
This 171 square metre apartment sleeps eight guests and features three bedrooms and three bathrooms, a gourmet kitchen with a Viking range, multiple living spaces including a bonus room with a gas fireplace, and private outdoor entertaining areas with a fire pit and Adirondack chairs.
Peace And Quiet On The Lake - The Berkshires, MA
9.6 284 reviews

Peace And Quiet On The Lake

apartment, Becket
This charming house is located in Sherwood Forest, just 3.5 kilometres from Pyramid Lake and within 10 kilometres of both Iroquois Waterfront and October Mountain State Forest, offering a peaceful escape from the hustle and bustle. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This comfortable dwelling features two bedrooms, comfortably accommodating up to six guests. The kitchen is equipped with a refrigerator, oven, stovetop, microwave, and dishwasher, while the private garden provides a relaxing outdoor space with a barbecue grill.
Beautiful Berkshire Family Home - The Berkshires, MA
9.6 4 reviews

Beautiful Berkshire Family Home

apartment, Monterey
This private Berkshire post and beam house is located in a secluded woodland setting, offering privacy yet situated only 5 kilometres from Monterey village amenities, 19 kilometres from Butternut Family Skiing and Lake Garfield, and 16 kilometres from the Appalachian Trail.
This spacious 232 square metre dwelling, ideal for up to 12 guests across its 5 bedrooms and 3 bathrooms, boasts a well-equipped kitchen, throughout-house Wi-Fi, a wood-burning stove, and is pet-friendly, with outdoor recreation including swings and hammocks available.
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.7 212 reviews

The Meadows House @ Otis Ridge W/ 7-person Hot Tub

apartment, Otis
This three-bedroom apartment is situated in a peaceful neighbourhood near Otis Ridge Ski Area, a short walk from the slopes and a scenic drive from Great Barrington, Tanglewood, and Jacob's Pillow. The apartment has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment comfortably sleeps up to seven guests and features a well-equipped kitchen, a private garden, a hot tub with mountain views, a spacious deck, and a fireplace. Guests can enjoy a range of activities including skiing, exploring the surrounding mountains, and visiting nearby cultural attractions.

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Best The Berkshires, MA accommodations with a balcony

Lakeside 3-br Berkshires Residence - The Berkshires, MA
9.6 8 reviews

Lakeside 3-br Berkshires Residence

apartment, Becket
This Becket lakeside property offers direct Pyramid Lake access and is located 3.7km from Jacob's Pillow dance centre.
The 149 square metre house sleeps six, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a jacuzzi, terrace, garden, parking, and on-site hot tub.
Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes - The Berkshires, MA
10 1 review

Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes

apartment, Otis
This apartment in Otis is located by a river, offering a secluded woodland experience close to Hayes Pond (200 metres) and within 13 kilometres of Otis Reservoir and the Appalachian Trail.
This 178 square metre dwelling accommodates up to 10 guests with 3 bedrooms and 3 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace or balcony, and garden access, with pets and families welcome.
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.
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.

Best The Berkshires, MA accommodations with a kitchen

Sky Light Lighthouse Unique Getaway In Berkshires - The Berkshires, MA
9.8 35 reviews

Sky Light Lighthouse Unique Getaway In Berkshires

apartment, New Marlborough
This lighthouse-style house in New Marlborough, Massachusetts, is within walking distance of the Joffe Nature Sanctuary and Umpachene Falls, and a short drive from hiking trails around York Lake.
The property, sleeping up to two guests, offers a modern interior with an octagonal kitchen/living room, upstairs bedroom and bathroom, a rooftop deck, and a large three-season screened porch; high-speed internet and pet-friendly facilities are also available.
Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires, MA
9.9 186 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

cabin, New Marlborough
This one-bedroom cabin in New Marlborough is situated beside the Umpachene River, a short distance from the Appalachian Trail and the town centre.
The cabin is equipped with a well-equipped kitchen, a private sauna, and an outdoor shower, comfortably accommodating up to four guests.
Sailor & Queen: Artist-inspired Berkshire Home - The Berkshires, MA
10 5 reviews

Sailor & Queen: Artist-inspired Berkshire Home

apartment, Otis
This garden-level suite in Otis is located in the Berkshires, offering a secluded natural setting with artist-crafted touches.
This 2-bedroom, 1-bathroom flat accommodates up to 4 guests, featuring a kitchen, garden, and parking, ideal for a peaceful retreat in the Berkshires.
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.8 47 reviews

The Meadows House @ Otis Ridge W/ 7-person Hot Tub

apartment, Otis
This house is located just half a mile from Otis Ridge, offering easy access to hiking trails and scenic views. It is also within a short drive of County Beach, Ashintully Gardens, Otis Reservoir, and Jacob's Pillow, making it a great base for exploring the area. The property has received excellent user ratings, suggesting a comfortable and enjoyable stay.
The house has three bedrooms, three bathrooms, and can accommodate up to seven guests, with a total floor area of 153 square metres. It features a fully equipped kitchen, a fireplace, a spa tub, a garden, barbecue grills, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
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