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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)

Lg 1 Bd - Vacation Village in the Berkshires
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

COZY CABIN IN BERKSHIRES RESORT
COZY CABIN IN BERKSHIRES RESORT
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
8.6 out of 10, Excellent, (10)

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, (1799)
The price is SAR 409
SAR 490 total
includes taxes & fees
29 Apr - 30 Apr

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (928)
The price is SAR 503
SAR 562 total
includes taxes & fees
28 Apr - 29 Apr

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
The price is SAR 841
SAR 940 total
includes taxes & fees
9 May - 10 May
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
5/5 Excellent
"Great for Family Vacation...will be back!"
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Posted 2 days ago
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