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Compare 42 Resorts in Chatham 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
8.6 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 Chatham

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1794)
The price is SAR 409
SAR 490 total
includes taxes & fees
14 Apr - 15 Apr

Postcard Cabins Eastern Catskills
Postcard Cabins Eastern Catskills
8.0 out of 10, Very Good, (7)
The price is SAR 657
SAR 709 total
includes taxes & fees
10 Apr - 11 Apr

Micosta Leisure Inn
Micosta Leisure Inn
9.2 out of 10, Wonderful, (94)
The price is SAR 487
SAR 527 total
includes taxes & fees
18 Apr - 19 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 Chatham hotels
Recent reviews of Chatham hotels

The Red Lion Inn
5/5 Excellent
"The staff was absolutely amazing, very accommodating and friendly. Overall we had a wonderful experience!! "
A verified traveler stayed at The Red Lion Inn
Posted 8 hours ago
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