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Compare 1,593 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chatham hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₩175,230
₩195,731 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1003)
"Wonderful place to stay"
The price is ₩173,086
₩193,342 total
includes taxes & fees
Sep 21 - Sep 22
The Yankee, Trademark Collection by Wyndham
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (692)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is ₩222,259
₩248,264 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold
Comfort Inn & Suites East Greenbush - Albany
Lobby

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
8.4 out of 10, Very Good, (1003)
"Room was great,great breakfast, great place to stay with convenient access to highway"
The price is ₩146,300
₩162,393 total
includes taxes & fees
Sep 2 - Sep 3
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1967)
"Beautiful location!"
The price is ₩149,867
₩182,580 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ₩176,656
₩251,415 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (527)
"Great place , love it, will return"
The price is ₩206,485
₩230,643 total
includes taxes & fees
Sep 15 - Sep 16
The Constance by the Lenox Collection
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Loved our visit"
The price is ₩275,332
₩369,360 total
includes taxes & fees
Sep 7 - Sep 8
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (703)
"Pleasant stay"
The price is ₩126,611
₩160,744 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (585)
"Amazing place to stay. Can’t wait to go again. "
The price is ₩106,197
₩149,532 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (863)
"Consistently a clean room with welcoming staff."
The price is ₩150,810
₩168,454 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
St. Charles Hotel
Free daily continental breakfast

St. Charles Hotel

2.0 star property
6.8 out of 10, (787)
"Very nice staff and comfy stay"
The price is ₩222,272
₩251,175 total
includes taxes & fees
Aug 27 - Aug 28
St. Charles Hotel
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (767)
"Close to our target event a plus"
The price is ₩98,373
₩109,884 total
includes taxes & fees
Sep 7 - Sep 8
FairBridge Inn Express
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Free buffet breakfast

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

2.5 star property
8.8 out of 10, Excellent, (822)
"Very nice accommodations; very clean & affordable pricing! "
The price is ₩175,715
₩195,043 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (20)
"Really enjoyed my stay here, definitely need a car to get around"
The price is ₩186,991
₩208,870 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
the Alander
Dinner served, American cuisine

the Alander

2.5 star property
9.0 out of 10, Wonderful, (155)
"Loved our stay, staff very attentive and helpful!! "
The price is ₩221,373
₩247,938 total
includes taxes & fees
Aug 24 - Aug 25
the Alander
Howard Hotel
Front of property

Howard Hotel

2.0 star property
10.0 out of 10, Exceptional, (63)
"Nice location, easy walk to dining & boutiques."
The price is ₩188,887
₩213,443 total
includes taxes & fees
Sep 1 - Sep 2
Howard Hotel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (625)
"It was lovely!"
The price is ₩88,203
₩98,522 total
includes taxes & fees
Sep 7 - Sep 8
Econo Lodge Lee - Great Barrington
The Wick, Hudson, A Tribute Portfolio Hotel
Hiking

The Wick, Hudson, A Tribute Portfolio Hotel

4.0 star property
8.8 out of 10, Excellent, (532)
"Gorgeous hotel next to the adorable historic district "
The price is ₩297,470
₩336,142 total
includes taxes & fees
Sep 2 - Sep 3
The Wick, Hudson, A Tribute Portfolio Hotel
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (60)
"Really beautiful place to enjoy nature with family!!"
The price is ₩233,825
₩304,830 total
includes taxes & fees
Aug 24 - Aug 25
Postcard Cabins Eastern Catskills
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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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

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
"This place is it's own oasis in the Berkshires. Very nice place which was clean and the folks we talked to at the front desk were very very nice and helpful! It would be tough for someone who has any mobility issues, no elevator and even we had a really hard time getting into and out of the tub/shower and we don't have mobility issues."
Holly 2-night trip
Posted 22 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 traveler data. Other good options for your trip to the area are Berkshire Mountain Lodge and FairBridge Inn Express. 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! The majority of hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chatham.

Where can I learn more about changing or cancelling my trip to Chatham?

To access more information about rescheduling or cancelling your trip to Chatham, head over to our customer service page.

Where is the best place to stay close to The Mac-Haydn Theatre?

Charming Farm House on 460 Acre Working Farm is one of the top choices for your stay based on our traveler data, and this property features in-room kitchens and private patios. It's located 2.6 mi (4.1 km) from The Mac-Haydn Theatre. Other good choices within 5 miles include Chatham Travel Lodge and Mile Hill B&B.

What are some accommodations 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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG are a couple of other choices with an onsite pool. View all hotels with pools in Chatham.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What is staying in Chatham like?

Visitors can enjoy all that Chatham has to offer including the theaters and restaurants. This city also attracts tourists with its welcoming locals. In Chatham, there are 23 hotels and other accommodations to choose from. Find out more about Chatham.

What should I do while I'm visiting Chatham?

A favorite place to visit is The Mac-Haydn Theatre. You'll also find Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site in the area. Check out what more to see and do in Expedia's Chatham guide.

What's the seasonal weather like in Chatham?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.