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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Chatham Resorts

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Other property types in Chatham

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1794)
"The location to jimney peak was great."
The price is CA $147
CA $177 total
includes taxes & fees
Apr 16 - Apr 17
Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very good, (7)
"We always live these cabins & we've been coming for years!"
The price is CA $249
CA $269 total
includes taxes & fees
Apr 10 - Apr 11
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (94)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is CA $183
CA $198 total
includes taxes & fees
Apr 20 - Apr 21
Micosta Leisure Inn
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.

Frequently asked questions

What can I expect from a resort vacation in Chatham?
You deserve a break, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Chatham. One of the comfortable resort hotels in the surrounding area might be just what you’re looking for, whether you’re hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chatham?
Here are our top-rated resorts around Chatham: All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Situated just a 5-minute walk from Jiminy Peak Mountain Resort. 20.5 mi (33 km) from Chatham. Features a sauna. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Amenities include ski-in/ski-out access, a fitness center, and a garden. SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires! - Ski resort steps from Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Access to ski-in/ski-out access, a fitness center, and beach sun loungers.
What can I do in Chatham?
Experience the local theater scene at The Mac-Haydn Theatre, or bring the kids to Berkshire Botanical Garden for some family fun. In the area, other attractions include Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site.
What's the seasonal weather like in Chatham?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Chatham?
Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.