Find Family Hotels in Chatham, NY

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Check availability on Chatham Family Hotels

Our top choices for Chatham family-friendly hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1001)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NT$3,163
NT$3,534 total
includes taxes & fees
Jan 8 - 2026/1/9
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is NT$3,836
NT$4,902 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (989)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is NT$2,923
NT$3,265 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,388
NT$2,667 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Plus Berkshire Hills Inn & Suites

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is NT$4,257
NT$4,755 total
includes taxes & fees
Jan 19 - 2026/1/20
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Four Points by Sheraton Albany

Four Points by Sheraton Albany
3.0 star property
Albany
9.0 out of 10, Wonderful, (548)
"Great stay. Highly recommend. "
United States
Robert
The price is NT$3,532
NT$4,044 total
includes taxes & fees
Dec 22 - Dec 23
Four Points by Sheraton Albany

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is NT$2,365
NT$2,642 total
includes taxes & fees
Dec 21 - Dec 22
Travelodge by Wyndham Great Barrington Berkshires

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (650)
"The room was clean and the service adequate"
United States
David
The price is NT$1,901
NT$2,123 total
includes taxes & fees
Jan 5 - 2026/1/6
Econo Lodge Lee - Great Barrington

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (13)
"New hotel very nice"
United States
joel
The price is NT$4,258
NT$4,756 total
includes taxes & fees
Jan 4 - 2026/1/5
Element Lenox Berkshires

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.4 out of 10, Very Good, (1000)
"Great location and easy off/on thruway 90 as well as many food, shopping options."
United States
Gail
The price is NT$3,023
NT$3,355 total
includes taxes & fees
Jan 11 - 2026/1/12
Comfort Inn & Suites East Greenbush - Albany
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.

Top Chatham Hotel Reviews

Frequently asked questions

What's Chatham like for family-friendly vacations?
If you've been thinking about a trip with your kids, the welcoming destination of Chatham is a good choice. The theaters and restaurants are just a few things that make this the ideal place for a family vacation. Arrange a flight into Hudson, NY (HCC-Columbia County), which is the closest airport, or Pittsfield, MA (PSF-Pittsfield Municipal), which is located 16 mi (25.8 km) from the city center.
When's the best time to book a family-friendly vacation 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 there to see and do with your family in Chatham?
The Mac-Haydn Theatre, Hudson Opera House, and Max and Lillian Katzman Theater are interesting attractions you and your family will enjoy exploring while you are staying in Chatham. Make sure you have lots of time for activities like Tanglewood Music Center and Catamount Ski Area.

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