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8 Dec - 9 Dec
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Top hotels and accommodation in Chatham

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)
"Very clean rooms and excellent staff."
United States
Kenneth R.
Travelling for leisure
The price is AU$157
includes taxes & fees
10 Dec - 11 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, (1005)
"the rooms were really nice and clean"
United States
Devin
Travelling with partner
The price is AU$150
includes taxes & fees
15 Dec - 16 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, (705)
"It is conveniently located just a short drive from Great Barrington"
United States
Sudhendu
Travelling with family
The price is AU$172
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Corner Studio
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.0 out of 10, Very good, (8)
"Lovely room and great products in the room."
United States
Crys
Travelling solo
The price is AU$466
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 AU$220
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)
"Very cute and clean room."
United States
Karen
Travelling for leisure
The price is AU$171
includes taxes & fees
10 Dec - 11 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, (983)
"Our room was very spacious, clean and comfortable."
United States
Priscilla
The price is AU$154
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Room, 1 Queen Bed, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (804)
"White bathroom was very clean"
United States
Evelyn
Travelling with partner
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)
"But overall it was good, convenient location"
United States
Karen
The price is AU$133
includes taxes & fees
28 Dec - 29 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, (1003)
"the rooms were clean and comfortable"
United States
Elisabeth
Travelling for leisure and business
The price is AU$170
includes taxes & fees
17 Dec - 18 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, (781)
"Comfortable bed, spacious rooms, nice kitchenette and appliances, friendly staff, nice pool, wi-fi excellent, and great price."
United States
Denis
Travelling with partner
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, (979)
"The room was nice and clean."
United States
Ashley
Travelling for leisure
The price is AU$135
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, (2168)
"Very clean, lots of amenities, and spacious rooms!"
United States
Sandra
Travelling with partner
The price is AU$166
includes taxes & fees
9 Dec - 10 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)
"Room was clean and comfortable"
United States
Richard
Travelling with partner
The price is AU$127
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)
"My wife and I are both 76 and able to get around very nicely"
United States
Armand
Travelling with partner
The price is AU$318
includes taxes & fees
8 Jan - 9 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)
"Was looking forward to relaxing in the pool"
United States
Mark
Travelling for leisure
The price is AU$174
includes taxes & fees
21 Dec - 22 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)
"Very pleasant and nicely decorated room."
United States
Debra
Travelling for leisure
The price is AU$199
includes taxes & fees
6 Jan - 7 Jan 2026
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)
"The room was clean and spacious."
United States
Karen
Travelling for leisure
The price is AU$133
includes taxes & fees
9 Dec - 10 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)
"This is a quaint B&B, very conveniently located;"
United States
Ellen
Travelling with partner
The price is AU$253
includes taxes & fees
9 Dec - 10 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

Recent Reviews in Chatham

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"We loved our stay at the brand new Pocketbook Hotel! Our room was lovely and the bed/pillows were great."
Marla 2-night trip
Posted 2 days ago
Pocketbook Hotel and Bath

More cheap accommodation in Chatham

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY
The price is AU$158 per night from 8 Jan to 9 Jan
AU$158
8 Jan - 9 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.
What are some of the best holiday rentals that Chatham has to offer?
Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Chatham is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all 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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