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28 Nov - 29 Nov
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29 Nov - 30 Nov
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Top 10 Chatham hotels and places to stay

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, (1005)
"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 ฿3,423
฿3,824 total
includes taxes & fees
18 Dec - 19 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1011)
"Great stay!"
United States
Ann
The price is ฿2,013
฿2,249 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (803)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ฿2,985
฿3,334 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Untold
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
The price is ฿2,386
฿3,019 total
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires
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, (1003)
"Room was spotless, staff very friendly."
United States
amber
The price is ฿3,258
฿3,617 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn & Suites East Greenbush - Albany
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, (972)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ฿2,992
฿3,342 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property amenity
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 ฿3,431
฿4,282 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ฿4,150
฿5,895 total
includes taxes & fees
30 Nov - 1 Dec
The Cornell Inn, Lenox & The Berkshires
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ฿4,898
฿6,910 total
includes taxes & fees
21 Dec - 22 Dec
The Red Lion Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (769)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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, (62)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ฿3,067
฿3,426 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Free buffet breakfast
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

2.5 star property
Rensselaer
8.8 out of 10, Excellent, (855)
"Friends visiting our church stayed here -- and they thought it was great! Treated very nicely by the staff; great view of Albany's skyline."
United States
Nicholas
The price is ฿2,938
฿3,261 total
includes taxes & fees
5 Dec - 6 Dec
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Front of property
Howard Hotel

Howard Hotel

2.0 star property
Hudson
10.0 out of 10, Exceptional, (101)
"Lovely hotel in a very good location near to many shops and dining options. The room Was clean with comfortable beds. "
United States
Sandra
The price is ฿4,399
฿4,971 total
includes taxes & fees
10 Dec - 11 Dec
Howard Hotel
Free daily continental breakfast
St. Charles Hotel

St. Charles Hotel

2.0 star property
Hudson
6.8 out of 10, (848)
"The breakfast and proximity to everything. "
United States
Mary-Linda
The price is ฿5,175
฿5,848 total
includes taxes & fees
1 Dec - 2 Dec
St. Charles Hotel
Premium bedding, memory-foam beds, individually decorated
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (123)
"We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. "
United States
Robin
The price is ฿3,828
฿4,440 total
includes taxes & fees
1 Dec - 2 Dec
Nautical Nest
American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (184)
"Very nice clean place in a beautiful area. "
United States
Wayne
The price is ฿5,154
฿5,772 total
includes taxes & fees
3 Dec - 4 Dec
the Alander
Hiking
The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel

4.0 star property
Hudson
8.8 out of 10, Excellent, (540)
"Very nice hotel Great staff, clean and modern Unique restoration of an old candle factory Highly recommend if you're in Hudson NY "
United States
Thomas
The price is ฿6,544
฿7,395 total
includes taxes & fees
29 Dec - 30 Dec
The Wick, Hudson, A Tribute Portfolio Hotel
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is ฿4,186
฿4,688 total
includes taxes & fees
1 Dec - 2 Dec
Micosta Leisure Inn
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is ฿4,298
฿4,801 total
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Double Room | Egyptian cotton sheets, premium bedding, memory-foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (116)
"Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx"
United States
Savannah
The Brooks Motel
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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Stay near popular Chatham attractions

The Mac-Haydn Theatre

You can make plans for a show at The Mac-Haydn Theatre during your trip to Chatham. Stroll along this trendy area's riverfront or simply enjoy its cafes.
See properties

Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

See all hotels in Chatham
Tracy Memorial Village Hall, Chatham, New York

Top Chatham Hotel Reviews

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

10/10 Excellent
"Great"
Vanessa 1-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Chatham

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY
The price is ฿3,258 per night from 29 Dec to 30 Dec
฿3,258
฿3,617 total
29 Dec - 30 Dec
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)

Frequently asked questions

What's the best place to stay in Chatham?
Located 20.8 mi (33.5 km) from the heart of Chatham, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chatham.
If I need to cancel my hotel reservation in Chatham, will I receive a refund?
Yes! Most hotel room reservations are refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chatham.
What are some accommodation options with pools in Chatham?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Chatham.
What is staying in Chatham like?
Visitors can enjoy all that Chatham has to offer, including the theatres and restaurants. This city also attracts tourists with its welcoming locals. In Chatham, there are 25 hotels and other accommodation options to choose from. Find out more about Chatham.
What are the top places to visit in Chatham?
A favourite place to visit is The Mac-Haydn Theatre. You'll also find Martin Van Buren National Historic Site and Kinderhook Lake in the area. Take a look at what more there is to see and do in Expedia's Chatham guide.
What's the seasonal weather 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.

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