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Compare 539 Vacation Homes in Chatham with updated reviews, rates, and availability.

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 838 total
includes taxes & fees
16 Apr - 17 Apr

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is SAR 2,060
SAR 3,882 total
includes taxes & fees
28 Mar - 29 Mar

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)

Lakeside Retreat Just You, The Lake & The View!
Lakeside Retreat Just You, The Lake & The View!
9.8 out of 10, Exceptional, (69)

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (25)
The price is SAR 596
SAR 1,248 total
includes taxes & fees
27 Apr - 28 Apr

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
9.0 out of 10, Wonderful, (22)

Secluded Lux Mansion Pool Home with Amazing Views
Secluded Lux Mansion Pool Home with Amazing Views
10.0 out of 10, Exceptional, (1)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (69)
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, (1792)
The price is SAR 484
SAR 572 total
includes taxes & fees
1 Apr - 2 Apr

Postcard Cabins Eastern Catskills
Postcard Cabins Eastern Catskills
8.4 out of 10, Very Good, (5)
The price is SAR 657
SAR 709 total
includes taxes & fees
2 Apr - 3 Apr

Micosta Leisure Inn
Micosta Leisure Inn
9.2 out of 10, Wonderful, (94)
The price is SAR 487
SAR 526 total
includes taxes & fees
15 Apr - 16 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

Vacation Village in the Berkshires
5/5 Excellent
"The location to jimney peak was great."
A verified traveler stayed at Vacation Village in the Berkshires
Posted 13 hours ago
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