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Compare 545 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, (245)
The price is AED 551
AED 837 total
includes taxes & fees
14 May - 15 May

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,016
AED 3,810 total
includes taxes & fees
14 May - 15 May

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

Stay Lakeside This Summer!
Stay Lakeside This Summer!
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!
9.2 out of 10, Wonderful, (23)

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, (72)
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, (1804)
The price is AED 434
AED 525 total
includes taxes & fees
14 May - 15 May

Postcard Cabins Eastern Catskills
Postcard Cabins Eastern Catskills
8.8 out of 10, Excellent, (11)
The price is AED 621
AED 809 total
includes taxes & fees
14 May - 15 May

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (929)
The price is AED 488
AED 545 total
includes taxes & fees
15 May - 16 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

Hotel On North
5/5 Excellent
"We loved this boutique hotel!"
A verified traveler stayed at Hotel On North
Posted 1 day ago
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