Berkshire County Holiday Rentals
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Our top choices for Berkshire County holiday rentals
Condo in Williamstown
Vacation Village in the Berkshires8.8 out of 10, Excellent, (2181)
"Awesome for ski"
Lazar
The price is HK$809
HK$989 total
includes taxes & fees
4 Jan - 5 Jan 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 HK$1,704
HK$1,903 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
Fred W.
The price is HK$1,205
HK$2,006 total
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is HK$1,134
HK$2,910 total
includes taxes & fees
22 Dec - 23 Dec
Apartment in Hancock
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
Carrie C.
The price is HK$1,144
HK$2,251 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Home in Sherwood Forest
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
James D.
The price is HK$1,247
HK$3,009 total
includes taxes & fees
22 Dec - 23 Dec
Apartment in Hancock
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor10.0 out of 10, Exceptional, (3)
"Stayed one night at one of my favorite ski spots. Will be back again!"
Neil J.
The price is HK$1,144
HK$2,251 total
includes taxes & fees
22 Dec - 23 Dec
Holiday 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 HK$1,430
HK$2,638 total
includes taxes & fees
23 Dec - 24 Dec
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
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
