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Check availability on Chatham Family-Friendly Hotels

Tonight
26 Nov - 27 Nov
Tomorrow
27 Nov - 28 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chatham Family-Friendly Hotels

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 3.454.601 ₫
3.858.789 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
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, (1002)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is 2.465.161 ₫
2.753.585 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Best Western Plus Berkshire Hills Inn & Suites
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, (971)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.354.492 ₫
2.629.967 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.616.003 ₫
2.922.075 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (1004)
"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 2.801.919 ₫
3.129.743 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
In-room safe, desk, free cots/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, (560)
"The staff were very friendly and accommodating "
United States
Tom
The price is 1.977.825 ₫
2.209.362 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Travelodge by Wyndham Great Barrington Berkshires
Indoor pool
Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

2.5 star property
West Coxsackie
7.6 out of 10, Good, (72)
"Refreshed property with welcoming check in. Comfortable work night stay."
United States
Sean
The price is 2.299.551 ₫
2.483.515 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Spark by Hilton West Coxsackie
Egyptian cotton sheets, premium bedding, down duvets, minibar
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (14)
"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 6.856.460 ₫
8.542.358 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Prospect Berkshires
Arcade
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, (790)
"Place was great!"
United States
Benjamin
The price is 2.808.512 ₫
3.505.246 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (1002)
"Room was spotless, staff very friendly."
United States
amber
The price is 2.667.427 ₫
2.960.844 ₫ total
includes taxes & fees
20 Dec - 21 Dec
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.
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Top Chatham Hotel Reviews

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Frequently asked questions

What's Chatham like for family-friendly holidays?
If you've been thinking about a trip with your children, the welcoming destination of Chatham is a good choice. The theatres and restaurants are just a couple of things that make this the ideal place for a family holiday. 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 centre.
When's the best time to book a family-friendly holiday in Chatham?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm 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 that you and your family will enjoy exploring while you are staying in Chatham. Make sure that you have lots of time for activities such as Tanglewood Music Center and Catamount Ski Area.