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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, (243)
The price is SAR 563
SAR 859 total
includes taxes & fees
3 May - 4 May

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is SAR 2,059
SAR 3,882 total
includes taxes & fees
30 Apr - 1 May

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

Lakeside Oasis Just You, The Lake & The View!
Lakeside Oasis Just You, The Lake & The View!
9.8 out of 10, Exceptional, (70)

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)

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, (70)
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, (1800)
The price is SAR 475
SAR 562 total
includes taxes & fees
11 May - 12 May

Postcard Cabins Eastern Catskills
Postcard Cabins Eastern Catskills
8.6 out of 10, Excellent, (10)
The price is SAR 469
SAR 648 total
includes taxes & fees
30 Apr - 1 May

Micosta Leisure Inn
Micosta Leisure Inn
9.2 out of 10, Wonderful, (96)
The price is SAR 487
SAR 526 total
includes taxes & fees
13 May - 14 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 Chatham hotels
Recent reviews of Chatham hotels

Comfort Inn & Suites East Greenbush - Albany
5/5 Excellent
"It was very nice just walking into the hotel. The breakfast varieties are also appreciated. Rooms are spacious."
A verified traveler stayed at Comfort Inn & Suites East Greenbush - Albany
Posted 20 hours ago
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