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Check prices for these dates

Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar
In one month
20 Mar - 22 Mar
In two months
17 Apr - 19 Apr
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
Renovated house. Built in 1890s. No neighbors in sight.
Fridge, microwave, oven, stovetop

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Loved our stay! Beautiful place and the hosts were very nice. Thank you!"
United States
Kate C.
HunnyHAUS: Deluxe TINY*private spa*walk to town
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,003 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is SAR 316
SAR 353 total
includes taxes & fees
1 Mar - 2 Mar
Quality Inn Lee - Lenox South
Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is SAR 219
SAR 241 total
includes taxes & fees
17 Feb - 18 Feb
Pleasant Valley Motel West Stockbridge
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, (1,000 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is SAR 360
SAR 402 total
includes taxes & fees
1 Mar - 2 Mar
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, (153 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is SAR 411
SAR 606 total
includes taxes & fees
23 Feb - 24 Feb
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (18 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is SAR 521
SAR 582 total
includes taxes & fees
22 Feb - 23 Feb
Element Lenox Berkshires
Exterior

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.6 out of 10, Excellent, (1,002 reviews)
"I have stayed here many times and have had good experiences always."
United States
Scott
The price is SAR 379
SAR 421 total
includes taxes & fees
28 Feb - 1 Mar
Comfort Inn & Suites East Greenbush - Albany
Lobby

Fairfield Inn & Suites Albany East Greenbush

Fairfield Inn & Suites Albany East Greenbush
3.0 star property
East Greenbush
8.6 out of 10, Excellent, (1,001 reviews)
"Breakfast was good, hotel was quiet, liked the water and tea in the lobby."
United States
Lily
The price is SAR 379
SAR 421 total
includes taxes & fees
6 Mar - 7 Mar
Fairfield Inn & Suites Albany East Greenbush
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is SAR 374
SAR 411 total
includes taxes & fees
2 Mar - 3 Mar
Shaker Mill Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (87 reviews)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
The price is SAR 392
SAR 436 total
includes taxes & fees
9 Mar - 10 Mar
Gregory House Country Inn
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, (822 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,003 reviews)
"Clean room, great location"
United States
Andrea
The price is SAR 284
SAR 317 total
includes taxes & fees
1 Mar - 2 Mar
Quality Inn Great Barrington
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, (93 reviews)
"clean place - would stay there again"
United States
Andradys
The price is SAR 335
SAR 362 total
includes taxes & fees
26 Feb - 27 Feb
Spark by Hilton West Coxsackie
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (856 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is SAR 453
SAR 506 total
includes taxes & fees
18 Feb - 19 Feb
Berkshires Untold
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (841 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is SAR 427
SAR 561 total
includes taxes & fees
17 Feb - 18 Feb
Berkshire Mountain Lodge
Signature Apartment | Private kitchen | Shared fridge, espresso maker, coffee/tea maker, electric kettle

Howard Hotel

Howard Hotel
2.0 star property
Hudson
10.0 out of 10, Exceptional, (117 reviews)
"Awesome hotel!"
United States
michael
Howard Hotel
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (831 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is SAR 259
SAR 289 total
includes taxes & fees
17 Feb - 18 Feb
Howard Johnson by Wyndham Lenox
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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Top Chatham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Incredible. The cabin was so cozy, clean, and the amenities were great! The host was so easy to communicate with and so responsive. We had an incredible view from our cabin, and just had the most relaxing time all round. "
Jessica 2-night trip
Posted 4 days ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Frequently asked questions

What can I expect from a resort vacation in Chatham?
You deserve a break, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Chatham. One of the comfortable resort hotels in the surrounding area might be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chatham?
Here are our top-rated resorts around Chatham: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY. - Ski resort right by Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Vacation Village In The Berkshires 5 Star Resort - Suite B - Family-friendly resort, 5-minute walk from Jiminy Peak Mountain Resort. 20.7 mi (33.3 km) from Chatham. Amenities include a fitness center, a car charging station, and a garden. Bentley Brook the perfect home base for exploring nearby Berkshire County - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 20.5 mi (33 km) from Chatham. Access to ski-in/ski-out access, a sauna, and a fitness center.
What can I do in Chatham?
Experience the local theater scene at The Mac-Haydn Theatre, or bring the kids to Berkshire Botanical Garden for some family fun. In the area, other attractions include Martin Van Buren National Historic Site and Kinderhook Lake.
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.
What's the best way to get to and around Chatham?
Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.