Places to stay in The Berkshires, MA

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The Berkshires, MA place to stay
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2574 Best places to stay in The Berkshires, MA

Best family friendly The Berkshires, MA lodging

Among the 2574 accommodations in The Berkshires, MA, here are the 4 best for families

Lakes & Leisure: Spacious Berkshire Getaway - The Berkshires, MA
10 6 reviews
The Berkshires, MA
24/07 – 26/07
694 €/nighttotal: 1388 € (2 )

Lakes & Leisure: Spacious Berkshire Getaway

4 4
apartment , Becket
This spacious Berkshire apartment in Becket offers easy access to nearby lakes perfect for kayaking and swimming.
Sleeping up to 12 guests, this four-bedroom, two-bathroom property boasts a well-equipped kitchen, multiple smart TVs, a garden, parking for three cars, and pet-friendly accommodation (maximum two dogs, £40 fee).
Cozy Guesthouse Minutes Away From Hiking! - The Berkshires, MA
9.8 212 reviews
The Berkshires, MA
31/08 – 03/09
177 €/nighttotal: 531 € (3 )

Cozy Guesthouse Minutes Away From Hiking!

1 2
house , New Marlborough
This charming guesthouse is situated in Southfield, a small village just 10km from Great Barrington, offering a peaceful retreat in the heart of the Berkshire countryside. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The guesthouse has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a king-size bed, a claw-foot bath, and a loft-style bedroom, making it ideal for a relaxing getaway. Guests can enjoy a range of nearby attractions, including Ski Butternut, hiking trails, and local restaurants, all within easy reach.
The Owl And Firefly  A Cabin For Families - The Berkshires, MA
10 1 review
The Berkshires, MA
26/08 – 02/09
594 €/nighttotal: 4158 € (7 )

The Owl And Firefly A Cabin For Families

3 1
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.
Little Longbow Lakefront Chalet - The Berkshires, MA
9.8 25 reviews
The Berkshires, MA
26/08 – 02/09
526 €/nighttotal: 3682 € (7 )

Little Longbow Lakefront Chalet

2 1
chalet , Becket
This Becket lakeside lodge is situated within 3.2km of Pyramid Lake, Jacob's Pillow Dance Festival, and 3km from October Mountain State Forest, offering easy access to swimming, boating, hiking and world-class dance performances.
Sleeping five guests, this two-bedroom, two-bathroom property boasts a private garden, terrace, spa, air conditioning, Wi-Fi, and barbecue facilities, perfect for a family getaway.

Best The Berkshires, MA accommodations with a fireplace

Mid-century Glass Octagon In The Berkshires - The Berkshires, MA
9.9 466 reviews
The Berkshires, MA
31/08 – 03/09
387 €/nighttotal: 1161 € (3 )

Mid-century Glass Octagon In The Berkshires

1 2
chalet , Otis
This charming chalet is located in a secluded woodland setting in Otis, Massachusetts, just 20 kilometres from Great Barrington and close to cultural attractions like Tanglewood and Jacob's Pillow. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The chalet has one bedroom and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a modern wood-burning fireplace, a fully equipped kitchen, an expansive deck with a fire pit, and a unique octagonal design offering stunning views of the surrounding woodlands.
Sailor & Queen: Artist-inspired Berkshire Home - The Berkshires, MA
10 1 review
The Berkshires, MA
14/08 – 16/08
299 €/nighttotal: 598 € (2 )

Sailor & Queen: Artist-inspired Berkshire Home

1 2
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.
Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires, MA
9.8 66 reviews
The Berkshires, MA
31/08 – 03/09
1115 €/nighttotal: 3345 € (3 )

Forget-me-not By Avantstay | Bold Lakefront Escape

1 2
apartment , Monterey
This apartment is located in the Berkshires, a region in western Massachusetts, just 160 kilometers from Monterey, offering stunning views of Lake Garfield. It has received excellent ratings for its location, cleanliness and overall guest experience.
The property is a spacious home with a modern design, suitable for up to 12 guests. Enjoy a range of amenities, including a hot tub, sauna, a fully equipped kitchen, a large deck with a BBQ grill, a ping pong table, and a pool table for entertainment.
Becket Home With 3-season Porch Walk To Lake Access - The Berkshires, MA
8.0 1 review
The Berkshires, MA
14/08 – 17/08
269 €/nighttotal: 807 € (3 )

Becket Home With 3-season Porch Walk To Lake Access

2 2
house , Becket
This Becket holiday home is situated near lake access, approximately 29-30km from Tanglewood and the Norman Rockwell Museum.
The 76 square metre property offers two bedrooms, one bathroom, and sleeps up to 13 guests, boasting a fully equipped kitchen, free Wi-Fi, a three-season porch, and a fireplace; nearby attractions include Cranwell Spa & Golf Club (26km away).

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Best The Berkshires, MA accommodations with a balcony

Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires, MA
10 4 reviews
The Berkshires, MA
26/08 – 02/09
284 €/nighttotal: 1988 € (7 )

Scribe`s Stable | A/c Screened In Porch Sleeps 6

2 1
farm , Monterey
This renovated barn, a short drive (less than 2km) from Monterey Town Beach in Monterey, Massachusetts, provides easy access to Tanglewood, Butternut Ski Area, and the Appalachian Trail.
The 167 square metre property features two bedrooms, one bathroom, sleeping up to six guests, and includes a kitchen with microwave, air conditioning, a terrace, garden, parking, and Wi-Fi.
Lakes & Leisure! Spacious Berkshire Getaway - The Berkshires, MA
The Berkshires, MA
31/08 – 03/09
568 €/nighttotal: 1704 € (3 )

Lakes & Leisure! Spacious Berkshire Getaway

1 2
house , Becket
This Berkshire property offers a peaceful retreat in Becket, situated 25.75 kilometres from Cranwell Spa & Golf Club and 29 kilometres from Tanglewood Musical Center, with Norman Rockwell Museum 30.5 kilometres away and Bradley International Airport 64.37 kilometres distant.
This detached house, spanning 270 square metres, accommodates up to 23 guests with one bedroom, two bathrooms, a fully equipped kitchen, air conditioning, a terrace, and complimentary WiFi and parking.
The Meadows House @ Otis Ridge W/ 7-person Hot Tub - The Berkshires, MA
9.8 44 reviews
The Berkshires, MA
20/11 – 23/11
321 €/nighttotal: 963 € (3 )

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

4 5
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.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.5 62 reviews
The Berkshires, MA
20/11 – 23/11
1033 €/nighttotal: 3099 € (3 )

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 5
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.

Best The Berkshires, MA accommodations with a kitchen

Hartsville Barn In The Berkshires - The Berkshires, MA
9.9 36 reviews
The Berkshires, MA
31/08 – 03/09
261 €/nighttotal: 783 € (3 )

Hartsville Barn In The Berkshires

1 2
farm , New Marlborough
Hartsville Barn, a renovated 1860s post-and-beam property near New Marlborough, Massachusetts, offers easy access to the Appalachian Trail (under 4km away) and is within a short drive of Great Barrington (under 7km).
This self-catering property sleeps four guests in two king bedrooms, one on the ground floor and one in a loft, and features a fully equipped kitchen, a clawfoot bath, fiber wifi, and a fire pit in its large garden.
Simple, Rustic, Cozy Get Away - The Berkshires, MA
9.4 32 reviews
The Berkshires, MA
31/08 – 03/09
190 €/nighttotal: 570 € (3 )

Simple, Rustic, Cozy Get Away

1 2
cabin , Otis
This charming cabin in Otis is situated just one lot away from the lake, offering a shared dock and access to the water. The peaceful surroundings provide a tranquil escape from the everyday hustle and bustle.
The two-bedroom cabin can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, air conditioning, and a screened porch, perfect for enjoying the beautiful sunsets.
Fantastic Cottage In The Berkshire Mountains - The Berkshires, MA
9.9 300 reviews
The Berkshires, MA
13/11 – 16/11
466 €/nighttotal: 1398 € (3 )

Fantastic Cottage In The Berkshire Mountains

1 5
cabin , Monterey
This four-bedroom lodge is located just a short drive from the Appalachian Trail, Beartown State Forest, and Lake Garfield, offering a peaceful retreat in the heart of the Berkshire Mountains. It has received excellent ratings for its location, cleanliness, and overall experience.
The 232 square metre property features a fully equipped kitchen, two fireplaces, a hot tub, and a screened porch. Guests can enjoy hiking trails, kayaking, swimming, and access to a fire pit, as well as a selection of DVDs, games, and books.
Cozy Cabin In The Berkshires - The Berkshires, MA
9.7 426 reviews
The Berkshires, MA
26/08 – 02/09
190 €/nighttotal: 1330 € (7 )

Cozy Cabin In The Berkshires

2 1
cabin , Otis
This charming cottage in Otis, Massachusetts is just minutes from Jacob's Pillow, lakes, ponds, hiking trails, and biking paths, offering a peaceful retreat in a beautiful setting. It has consistently received excellent ratings for location, cleanliness, and user experience.
The two-bedroom property sleeps up to four guests and features an open-plan living area with a full kitchen, washer and dryer, a wood-burning stove, and auxiliary heating. Guests can enjoy the surrounding nature with plenty of opportunities for hiking, biking, swimming, and exploring, or work remotely with the provided Wi-Fi and good cell phone reception.
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