Find Family Hotels in Chatham, NY

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Check availability on Chatham Family Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Chatham Family Hotels

Lobby sitting area
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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is SAR 351
SAR 392 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is SAR 364
SAR 406 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Restaurant
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, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 345
SAR 385 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is SAR 492
SAR 549 total
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires
Exterior
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, (1003)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is SAR 380
SAR 424 total
includes taxes & fees
18 Dec - 19 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is SAR 976
SAR 1,216 total
includes taxes & fees
17 Dec - 18 Dec
Prospect Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds
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 SAR 281
SAR 314 total
includes taxes & fees
9 Dec - 10 Dec
Travelodge by Wyndham Great Barrington Berkshires
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat Lodge
Lobby
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, (1006)
"Room was spotless, staff very friendly."
United States
amber
The price is SAR 355
SAR 394 total
includes taxes & fees
8 Jan - 9 January 2026
Comfort Inn & Suites East Greenbush - Albany
Indoor pool
Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

2.5 star property
West Coxsackie
7.6 out of 10, Good, (76)
"Great staff "
United States
John
The price is SAR 327
SAR 353 total
includes taxes & fees
14 Dec - 15 Dec
Spark by Hilton West Coxsackie
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.
View all properties

Top Chatham Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Staff is absolutely amazing "
Mitchell 2-night trip
Posted 12 hours ago
Comfort Inn & Suites East Greenbush - Albany

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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 Tanglewood Music Center 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 Catamount Ski Area and FASNY Museum of Firefighting.