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Compare 492 Vacation Homes in Old 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 AED 551
AED 833 total
includes taxes & fees
31 Mar - 1 Apr

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,197
AED 4,030 total
includes taxes & fees
1 Apr - 2 Apr

Romantic Villa
Romantic Villa
10.0 out of 10, Exceptional, (21)

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 AED 584
AED 1,221 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)
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 Old Chatham

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! ASK ABOUT FANTASTIC DISCOUNT!
9.6 out of 10, Exceptional, (85)

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1792)
The price is AED 474
AED 560 total
includes taxes & fees
1 Apr - 2 Apr

Micosta Leisure Inn
Micosta Leisure Inn
9.2 out of 10, Wonderful, (94)
The price is AED 477
AED 516 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 Old Chatham hotels
Recent reviews of Old 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 1 day ago
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