A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

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Our top choices for Berkshire County holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,768 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is ฿2,685
฿3,366 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,219 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is ฿2,892
฿3,977 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

3. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is ฿27,278
฿38,951 total
includes taxes & fees
22 Oct - 23 Oct
Mayas Shangrila
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

4. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (190 reviews)
"Great stay"
United States
George
The price is ฿3,315
฿3,713 total
includes taxes & fees
1 Nov - 2 Nov
Micosta Leisure Inn
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ฿7,487
฿18,522 total
includes taxes & fees
31 Oct - 1 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

6. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is ฿4,903
฿13,528 total
includes taxes & fees
11 Nov - 12 Nov
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Berkshire County Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."
Rita 1-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Berkshire County

Vacation Apartments in Berkshire County

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