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Vacation rentals in Berkshire County

Vacation rentals in Berkshire County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Berkshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private, Cozy Studio in the Berkshires
SUPERHOSTEntire guest suite · 3 guests · 1 bed · 1 bath
Private, Cozy Studio in the Berkshires

Bright, cheery, peaceful and cozy studio apartment in a quiet rural town, near the attractions of the Berkshires and close to the many private schools: Hotchkiss, Berkshire and Salisbury. "Impeccably clean, gorgeous space, outstanding attention to detail. Laurie and Michael’s spot has the feel of staying at a boutique hotel for a better price than you would ever find at one, especially in western CT. " - Ramon C. Private entry, full bath, queen bed, stove, coffee/tea. Private & peaceful.

What guests are saying:

“Mike and Laurie's place was fantastic. It was very clean and comfortable. We throughly enjoyed our stay. There was a small winter storm while we were staying here and they kindly cleaned off our vehicle and took care of the driveway. Highly recommended. Thank you.”

Guest Apt. Near MCLA & MASS MoCA
SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
Guest Apt. Near MCLA & MASS MoCA

My sunny, comfortable guest apartment is located on the 2nd floor of a Victorian house in the Cady Hill Historic District, one of the oldest neighborhoods in North Adams. It has a private entrance. Off-street parking is available for one vehicle. Free, wifi/wireless access is included. The apartment is quiet and modern. There is a small sitting room off of the entry hall that that is perfect for two. The full kitchen has new appliances (range/oven; refrigerator; microwave), a tea kettle and coffee maker, a table and chairs, and cupboards stocked with essentials for light cooking (dishes, flatware, etc.). The bedroom has a queen bed, a bookcase and easy chair. There is a full bath with a tub and shower next to the bedroom. I provide sheets, blankets, bath towels and kitchen towels. The house is close to MASS MoCA (ten minute walk), MCLA (five minute walk), and just a few blocks away from downtown coffee shops and restaurants. Natural Bridge State Park and Windsor Lake are a five minute drive away. Williams College, Clark Art Institute, WCMA and the Williamstown Theatre Festival are accessible by car (fifteen minutes).

What guests are saying:

“We had a really wonderful stay at Diane’s. The apartment is a lot larger than it looks in photos, plenty of space for 2 people! Everything was very clean, communication was easy and prompt, and the apartment was conveniently located. Diane was a lovely host that left us some guides for hiking in the area and some local tips on where to eat. I would definitely stay here again! Diana was very thoughtful and left us hand sanitizer, face masks, and wipes for us to use, great touches during covid.”

'Silo Studio' Cottage
SUPERHOSTEntire guesthouse · 2 guests · 1 bed · 1 bath
'Silo Studio' Cottage

Charming and romantic,' Round' Cottage on the Santarella Estate in the Berkshires in Western Massachusetts. Formerly, the cottage was sculptor Henry Hudson Kitson's summer studio on the Santarella Estate. The two-story cottage has a charming bedroom with 35 foot high conical ceiling with canopied bed upstairs with views through massive, multi-paned "mill windows" to the trees and sky and out to the lily pond. The downstairs sitting room looks out on the babbling brook and lovely gardens.

What guests are saying:

“The Santarella property is truly amazing! As soon as you arrive on the grounds, it feels like you’re walking into a fairy tale. The grounds are truly amazing with gorgeous perennials in bloom and trails throughout the property. Denise and Dennis were welcoming hosts who provided extensive recommendations of restaurants and activities in the area. Communication was extremely prompt and we felt welcome immediately. The Silo Studio is an amazing space and arranged in a way that truly maximizes the space of the unique design. The window seat was my favorite spot where you have a view of the pond and beautiful landscaping. You can watch chipmunks, bunnies and all kinds of beautiful birds enjoying the landscape. This is a beautiful, unique stay that allows you to disconnect from the business of life. Highly recommended!”

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Popular amenities for Berkshire County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Berkshire County

Waldtreff - quiet grand cabin
Entire cabin
Waldtreff - quiet grand cabin
Price:€ 211 / night
Romantic, Chic Interlaken Cottage Stockbridge
Entire cottage
Romantic, Chic Interlaken Cottage Stockbridge
Price:€ 238 / night
Sweet Brookside Cottage
SUPERHOSTEntire cottage
Sweet Brookside Cottage
Price:€ 94 / night
Hideaway with Spectacular Berkshire Views
SUPERHOSTEntire apartment
Hideaway with Spectacular Berkshire Views
Price:€ 118 / night
The Old Red Barn
SUPERHOSTEntire loft
The Old Red Barn
Price:€ 111 / night
Potter House
SUPERHOSTPrivate room
Potter House
Price:€ 80 / night
Comfortable living in 1870's house!
SUPERHOSTPrivate room
Comfortable living in 1870's house!
Price:€ 36 / night
Glass Cabin in the Woods
Entire cabin
Glass Cabin in the Woods
Price:€ 296 / night
The old sawmill from 1771
SUPERHOSTEntire house
The old sawmill from 1771
Price:€ 103 / night
Berkshire Get Away in GB
SUPERHOSTEntire apartment
Berkshire Get Away in GB
Price:€ 115 / night
Large guest suite w/private bath in the Berkshires
SUPERHOSTPrivate room
Large guest suite w/private bath in the Berkshires
Price:€ 60 / night
Rustic Barn Studio Apartment
SUPERHOSTEntire cabin
Rustic Barn Studio Apartment
Price:€ 106 / night
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