Vacation Rentals in Berkshire County
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Our top choices for Berkshire County vacation rentals
Condo in Williamstown
Vacation Village in the Berkshires8.8 out of 10, Excellent, (2184)
"Awesome for ski"
Lazar
The price is ￥16,213
￥19,821 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Condo resort in Hancock
Jiminy Peak Mountain Resort8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
Huang
The price is ￥33,468
￥37,383 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Vacation Home in Florida
Florida Mountain Log Cabin10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is ￥31,970
￥57,082 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cabin in Sheffield
Guesthouse Cabin vacation rentals in Berkshire County10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
deborah d.
The price is ￥61,284
￥105,208 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vacation Home in Monterey
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
Kim H.
The price is ￥132,407
￥276,832 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Camping in Williamstown
Huttopia Berkshires10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
Cammie
The price is ￥31,578
￥35,273 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Vacation Home in Great Barrington
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
Roberta
The price is ￥88,278
￥198,415 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Apartment in Adams
Penthouse Apartment on Park Street9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
judy r.
The price is ￥18,112
￥38,196 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
Top Berkshire County Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about Berkshire County
Vacation Apartments in Berkshire County
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