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Our top choices for Chatham hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

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, (1,005 reviews)
  • cleanliness
    Tranquil Berkshire hideaway near Tanglewood with complimentary amenities.
"Very friendly and good Breakfast."
United States
Jesse
The price is ￥14,681
￥16,399 total
includes taxes & fees
Feb 9 - Feb 10
Best Western Plus Berkshire Hills Inn & Suites
View from property

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (135 reviews)
  • cleanliness
    Rustic cabins with patios nestled in the picturesque Eastern Catskills.
"I loved every single part of the stay "
United States
Srijana
The price is ￥18,528
￥26,736 total
includes taxes & fees
Jan 27 - Jan 28
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Experience a peaceful stay near Mahaiwe Performing Arts Center.
"Great place to stay for a night in Great Barrington. Walk to everything in town "
United States
robert
The price is ￥11,779
￥13,157 total
includes taxes & fees
Feb 9 - Feb 10
Quality Inn Great Barrington
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, (727 reviews)
  • cleanliness
    Unwind in the Berkshires with indoor pool and free hot breakfast each morning.
"Great property, very accommodating. "
United States
Shanice
The price is ￥16,660
￥18,609 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
  • cleanliness
    Relax in the Berkshires with pool access and complimentary breakfast daily.
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ￥21,642
￥24,175 total
includes taxes & fees
Feb 1 - Feb 2
Element Lenox Berkshires
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Enjoy views of the Berkshires at this comfortable retreat with seasonal outdoor pool.
"Very friendly staff comfy beds!"
United States
Giselle
The price is ￥14,426
￥16,114 total
includes taxes & fees
Feb 4 - Feb 5
The Yankee, Trademark Collection by Wyndham
In-room safe, blackout drapes, iron/ironing board, free WiFi

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.4 out of 10, Very Good, (17 reviews)
  • cleanliness
    Stay steps away from Hudson Station at this boutique hotel with spa services.
"The front desk was very helpful in making sure we had a good stay. "
United States
Mark
The price is ￥25,152
￥35,459 total
includes taxes & fees
Feb 17 - Feb 18
Pocketbook Hotel and Bath
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (818 reviews)
"Unbelieveably clean for the price."
United States
Micah
Monument Mountain Motel
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, (1,001 reviews)
  • cleanliness
    Serene retreat in Pittsfield with indoor pool and tranquil rooms near Tanglewood.
"Staff was very courteous and rooms clean."
United States
Steven
The price is ￥15,535
￥17,353 total
includes taxes & fees
Jan 30 - Jan 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
  • cleanliness
    Serene lakeside escape with water activities and complimentary perks.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥22,421
￥26,296 total
includes taxes & fees
Feb 7 - Feb 8
Lakehouse Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (444 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ￥16,069
￥17,628 total
includes taxes & fees
Jan 25 - Jan 26
Shaker Mill Inn
Lake

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, (1,001 reviews)
  • cleanliness
    Modern lakeside retreat with 24-hour fitness and scenic Tanglewood location.
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ￥15,757
￥17,600 total
includes taxes & fees
Feb 4 - Feb 5
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Serene Lee retreat a short drive from Tanglewood Music Center and local sights.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ￥13,102
￥14,635 total
includes taxes & fees
Feb 7 - Feb 8
Quality Inn Lee - Lenox South
Suite, Multiple Beds (2 Queen Beds with Sofa bed) | Pillowtop beds, in-room safe, desk, iron/ironing board

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, (990 reviews)
  • cleanliness
    Escape to the charming town of West Coxsackie with easy access to outdoor adventures.
"Great little property for travelers needing a short stay. Not too much to do in the immediate area but rooms were clean and everything was fresh and updated."
United States
Vincent
The price is ￥15,414
￥16,646 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (844 reviews)
  • cleanliness
    Experience Berkshires charm with onsite American dining and attentive service.
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is ￥13,747
￥15,356 total
includes taxes & fees
Jan 27 - Jan 28
Berkshires Untold
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ￥11,678
￥13,045 total
includes taxes & fees
Jan 26 - Jan 27
Travelodge by Wyndham Great Barrington Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (549 reviews)
  • cleanliness
    Explore scenic Great Barrington with free perks and helpful staff at this cozy motel.
"Perfect for pets "
United States
Maria
The price is ￥17,127
￥19,132 total
includes taxes & fees
Jan 26 - Jan 27
The Little Lion
Free daily continental breakfast

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
7.8 out of 10, Good, (90 reviews)
"clean place - would stay there again"
United States
Andradys
The price is ￥13,916
￥15,030 total
includes taxes & fees
Feb 1 - Feb 2
Spark by Hilton West Coxsackie
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (818 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cozy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is ￥15,366
￥20,642 total
includes taxes & fees
Feb 3 - Feb 4
Berkshire Mountain Lodge
Lobby

Fairfield Inn & Suites Albany East Greenbush

Fairfield Inn & Suites Albany East Greenbush
2.5 star property
East Greenbush
8.6 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Convenient Albany access with free breakfast and 24-hour fitness center.
"Breakfast was good, hotel was quiet, liked the water and tea in the lobby."
United States
Lily
The price is ￥15,361
￥17,049 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites Albany East Greenbush
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 Labor 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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Beautiful unique property! Very clean room and very friendly staff"
Iolanda 1-night trip
Posted 2 days ago
Berkshires Untold

More cheap stays in Chatham

Quality Inn

Quality Inn

170 Housatonic Street Lee MA
The price is ￥13,102 per night from Feb 7 to Feb 8
￥13,102
￥14,635 total
Feb 7 - Feb 8
includes taxes & fees
8.2/10 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 traveler data. Other good options for your trip to the area are Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chatham.
What are some of the best vacation home rentals in Chatham?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chatham vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all 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 Comfort Inn Glenmont - Albany South 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 25 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 Martin Van Buren National Historic Site and Kinderhook Lake 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.

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