Find hotels in Chatham, NY from ￥12,992

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Dec 13 - Dec 14
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Dec 14 - Dec 15
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Chatham hotels

Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (650)
Set in Lee, this motel offers fun mini golf on the property and free continental breakfast each morning. Just a short drive from Greenock Country Club and shopping at Lee Premium Outlets, guests appreciate the attentive staff and convenient free parking.
"The room was clean and the service adequate"
United States
David
The price is ￥9,800
￥10,947 total
includes taxes & fees
Dec 28 - Dec 29
Econo Lodge Lee - Great Barrington
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1002)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Center. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.
"Room was clean and comfortable; location was good with a breakfast restaurant next door. The in-house breakfast was OK, but we preferred an upgrade. Receptionist staff member was professional and pleasant. "
United States
Patrick
The price is ￥13,800
￥15,415 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn Lee - Lenox South
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
Relax at this inviting lodge near Catamount Ski Area featuring a seasonal outdoor pool and restaurant. After adventures, unwind in the sauna or garden, or sip drinks at the bar while enjoying free breakfast, WiFi, and parking.
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat Lodge
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

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, (804)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Center and Berkshire Theatre Festival.
"Place was great!"
United States
Benjamin
The price is ￥15,972
￥20,887 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Dinner served, American cuisine
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (188)
Discover tranquility at this countryside lodge featuring the North Star restaurant serving American cuisine for dinner. Enjoy free WiFi and parking while exploring nearby Undermountain Golf Course and Copake Town Park. Rooms offer rainfall showerheads for extra comfort.
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is ￥21,769
￥24,382 total
includes taxes & fees
Dec 16 - Dec 17
the Alander
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (788)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"This place is so peaceful and the staff is always helpful "
United States
Leona
The price is ￥15,377
￥20,658 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Berkshire Mountain Lodge
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Center. After working out in the 24-hour fitness center, savor Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"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 ￥15,736
￥17,577 total
includes taxes & fees
Dec 23 - Dec 24
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥28,130
￥32,992 total
includes taxes & fees
Dec 19 - Dec 20
Lakehouse Inn
Exterior
Chatham Travel Lodge

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (211)
Peaceful countryside motel offers daily housekeeping, free WiFi, and complimentary parking. Explore nearby attractions like The Mac-Haydn Theatre or Shaker Museum, with convenient access to Hudson Station and airport.
" Nice"
United States
Katherine
The price is ￥18,035
￥20,199 total
includes taxes & fees
Dec 20 - Dec 21
Chatham Travel Lodge
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (986)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transportation Center, this hotel offers peaceful accommodations with an indoor pool. Enjoy the fitness center, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theater.
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,443
￥16,133 total
includes taxes & fees
Dec 15 - Dec 16
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant
voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG
3.5 star property
Coxsackie
9.2 out of 10, Wonderful, (327)
Serene Coxsackie retreat offers peaceful riverfront ambiance, full-service spa, and 3 bars for relaxation. Enjoy the fitness center before exploring nearby Mcquade park. Travelers praise the helpful staff and convenient train station access.
"Beautiful room and very clean"
United States
Mariam
The price is ￥20,369
￥21,999 total
includes taxes & fees
Jan 4 - Jan 5, 2026
voco James Newbury Hudson Valley by IHG
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
Discover this charming motel in Lee with free WiFi and parking. The helpful staff ensures a welcoming stay while the seasonal outdoor pool provides refreshment. Nearby attractions include Lee Library and Tanglewood Music Center, with hiking trails waiting for exploration.
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is ￥13,994
￥15,632 total
includes taxes & fees
Dec 20 - Dec 21
Sunset Inn
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Center. Close to Colonial Theater and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.
"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 ￥12,702
￥14,188 total
includes taxes & fees
Dec 23 - Dec 24
Berkshire Inn
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness center or enjoy nearby skiing options. Tanglewood Music Center and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is ￥14,661
￥16,377 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Plus Berkshire Hills Inn & Suites
Front of property - evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
Minutes from Barrington Stage Company and Berkshire Athenaeum, this hotel offers comfortable rooms and attentive service. Just a 2-minute walk from Pittsfield Intermodal Transportation Center, enjoy room service and the convenient downtown location.
"Clean room and staff was super friendly"
United States
Yuen
The price is ￥23,168
￥25,878 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel On North
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness center. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is ￥16,079
￥17,960 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Lenox Pittsfield
Lobby
Pilgrim Inn

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332)
Experience countryside tranquility at this golf-adjacent hotel in Lee, where free WiFi and parking enhance your stay. Explore nearby Lee Library and Animagic Museum, or embrace seasonal activities like cross-country skiing and snowboarding.
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is ￥12,480
￥13,940 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Pilgrim Inn
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
Experience tranquility at this peaceful B&B in Lee, where deep-tissue massages and aromatherapy await. Just a 10-minute drive from Tanglewood Music Center, guests enjoy access to a hot tub, terrace, and snack bar while exploring nearby Berkshire attractions.
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Breakfast and dinner served, American cuisine
Four Points by Sheraton Albany

Four Points by Sheraton Albany

Four Points by Sheraton Albany
3.0 star property
Albany
9.0 out of 10, Wonderful, (546)
Modern Albany hotel near Crossgates Mall with an indoor pool and Best Brew Restaurant serving American cuisine. Business travelers appreciate the 24-hour fitness center, bar, and proximity to Albany International Airport, plus free WiFi and parking.
"Great stay. Highly recommend. "
United States
Robert
The price is ￥17,451
￥19,982 total
includes taxes & fees
Dec 22 - Dec 23
Four Points by Sheraton Albany
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥13,885
￥15,510 total
includes taxes & fees
Dec 23 - Dec 24
The Central Downtown Inn & Suites
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Chatham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA
The price is ￥11,631 per night from Dec 24 to Dec 25
￥11,631
￥12,992 total
Dec 24 - Dec 25
includes taxes & fees
9/10 Wonderful! (1,000 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 Comfort Inn Glenmont - Albany South and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chatham.
What are some of the best vacation home rentals in Chatham?
Pet Friendly Riverfront Home in Great Barrington: You might want to consider this vacation home rental near Chatham, which 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 vacation with amenities like 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! 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. Comfort Inn Glenmont - Albany South and Holiday Inn & Suites Pittsfield-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 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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