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Compare 36 Resorts in Cheshire with updated reviews, rates, and availability.

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
9.8 out of 10, Exceptional, (38)

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
10.0 out of 10, Exceptional, (3)

Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
9.6 out of 10, Exceptional, (4)

Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (2)

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
9.6 out of 10, Exceptional, (16)

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.8 out of 10, Excellent, (9)

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
9.6 out of 10, Exceptional, (4)
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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Other property types in Cheshire

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1792)
The price is SAR 446
SAR 531 total
includes taxes & fees
14 Apr - 15 Apr

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (925)
The price is SAR 503
SAR 552 total
includes taxes & fees
5 Apr - 6 Apr

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (240)
The price is SAR 563
SAR 859 total
includes taxes & fees
10 Apr - 11 Apr
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.
Recent reviews of Cheshire hotels
Recent reviews of Cheshire hotels

The Williams Inn
5/5 Excellent
"Nicest place in Williamstown. Excellent restaurant. Very comfortable room."
A verified traveler from Boston stayed at The Williams Inn
Posted 2 days ago
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