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)
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)
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)
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)
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)
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)
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)
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)
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
















































































