Chatham Hotels from ₹6,322

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6 Dec - 7 Dec
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7 Dec - 8 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Top 10 Chatham hotels and places to stay

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 ₹8,411
₹9,395 total
includes taxes & fees
16 Dec - 17 Dec
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is ₹8,030
₹8,970 total
includes taxes & fees
16 Dec - 17 Dec
The Yankee, Trademark Collection by Wyndham
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (703)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is ₹9,627
₹10,754 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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
8.0 out of 10, Very good, (8)
"The room was very nice, and the staff was great"
United States
Kienan
The price is ₹21,054
₹27,858 total
includes taxes & fees
28 Dec - 29 Dec
Pocketbook Hotel and Bath
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 ₹11,787
₹13,166 total
includes taxes & fees
15 Dec - 16 Dec
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is ₹9,711
₹10,653 total
includes taxes & fees
8 Dec - 9 Dec
Shaker Mill Inn
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, (981)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₹8,261
₹9,228 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ₹7,660
₹8,557 total
includes taxes & fees
15 Dec - 16 Dec
Berkshire Inn
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, (1002)
"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 ₹9,106
₹10,171 total
includes taxes & fees
16 Dec - 17 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (778)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Exterior
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

2.5 star property
West Coxsackie
8.4 out of 10, Very good, (978)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
The price is ₹7,469
₹8,067 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2165)
"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 ₹8,009
₹9,933 total
includes taxes & fees
7 Dec - 8 Dec
Vacation Village in the Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very good, (1000)
"clean warm room. breakfast was small but good enough to start the day. coffee was delicious. quiet which was nice and also very close to the town center with shops so that was convenient "
United States
Gisselle
The price is ₹6,808
₹7,604 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is ₹13,718
₹19,344 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Red Lion Inn
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ₹9,287
₹10,374 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Berkshires-Lenox
Premium bedding, memory-foam beds, individually decorated
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"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 ₹10,369
₹12,029 total
includes taxes & fees
7 Dec - 8 Dec
Nautical Nest
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is ₹7,108
₹7,940 total
includes taxes & fees
7 Dec - 8 Dec
Howard Johnson by Wyndham Lenox
Porch
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is ₹13,496
₹15,116 total
includes taxes & fees
17 Dec - 18 Dec
Changing Times Boutique Country Lodging
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"so quiet"
robert 7-night trip
Posted 5 days ago
Vacation Village in the Berkshires

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 ₹8,598 per night from 4 Jan to 5 Jan
₹8,598
₹9,544 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,001 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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