Find hotels in Chatham, NY from 1.839.871 ₫

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2 Dec - 3 Dec
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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, (1006)
"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 2.577.570 ₫
2.879.146 ₫ total
includes taxes & fees
22 Dec - 23 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, (1014)
"Great stay!"
United States
Ann
The price is 1.647.153 ₫
1.839.871 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2159)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is 2.149.591 ₫
2.690.318 ₫ total
includes taxes & fees
3 Dec - 4 Dec
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, (1000)
"Room was spotless, staff very friendly."
United States
amber
The price is 2.548.564 ₫
2.828.907 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Comfort Inn & Suites East Greenbush - Albany
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is 2.890.843 ₫
3.229.072 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Berkshires Untold
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, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is 2.615.408 ₫
2.921.410 ₫ total
includes taxes & fees
27 Dec - 28 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, (794)
"Place was great!"
United States
Benjamin
The price is 2.807.873 ₫
3.504.448 ₫ total
includes taxes & fees
9 Dec - 10 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, (1004)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is 3.734.114 ₫
5.201.901 ₫ total
includes taxes & fees
21 Dec - 22 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, (1004)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is 3.955.350 ₫
5.596.292 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Red Lion Inn
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, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is 2.404.488 ₫
2.685.812 ₫ total
includes taxes & fees
14 Dec - 15 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, (856)
"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 2.510.329 ₫
2.786.464 ₫ total
includes taxes & fees
5 Dec - 6 Dec
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (776)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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 3.599.376 ₫
4.067.296 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Howard Hotel
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 3.691.660 ₫
4.134.658 ₫ total
includes taxes & fees
3 Dec - 4 Dec
the Alander
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 3.132.162 ₫
3.633.307 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Nautical Nest
Free daily continental breakfast
St. Charles Hotel

St. Charles Hotel

2.0 star property
Hudson
6.8 out of 10, (853)
"The breakfast and proximity to everything. "
United States
Mary-Linda
The price is 2.891.361 ₫
3.267.383 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
St. Charles Hotel
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, (544)
"Close to Warren street, friendly staff, pet friendly and clean. We will stay again! "
United States
Carell
The price is 5.356.050 ₫
6.052.336 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Wick, Hudson, A Tribute Portfolio Hotel
Corner Studio | In-room safe, blackout curtains, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.8 out of 10, Excellent, (6)
"The room was very nice, and the staff was great"
United States
Kienan
The price is 6.169.410 ₫
8.163.131 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Pocketbook Hotel and Bath
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 3.425.868 ₫
3.837.162 ₫ total
includes taxes & fees
9 Dec - 10 Dec
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.
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Stay near popular Chatham attractions

The Mac-Haydn Theatre

This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labour Day.
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Everything was anazing. There were a couple touches needed to be finishished in our room though. But they just opened "
hans 1-night trip
Posted 6 days ago
Pocketbook Hotel and Bath

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 2.548.564 ₫ per night from 1 Jan to 2 Jan
2.548.564 ₫
2.828.907 ₫ total
1 Jan - 2 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)

Hotels in Chatham with star rating

Frequently asked questions

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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