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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Resorts in Chatham

No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"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.
The price is AED 790
AED 1,325 total
includes taxes & fees
18 Nov - 19 Nov
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, (6)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
United States
Melissa D.
The price is AED 790
AED 1,325 total
includes taxes & fees
17 Nov - 18 Nov
BLUSH: Boutique TINY home*private spa*walk to town
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"From the moment we walked in, the HunnyHaus felt like home—only better! Every detail was thoughtfully provided, from the fully stocked kitchen to cozy touches that made our stay so comfortable and relaxing. My husband and I kept saying throughout our trip that this was the perfect vacation. We were in the area for the John Williams Film Concert at Tanglewood performed by the Boston Pops, and the location was ideal. The hosts were incredible—friendly, responsive, and always ready with fantastic...
United States
Corey A.
HunnyHAUS: Deluxe TINY*private spa*walk to town
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)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 275
AED 307 total
includes taxes & fees
20 Nov - 21 Nov
Best Western Plus Berkshire Hills Inn & Suites
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, (693)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
The price is AED 393
AED 439 total
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (958)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
The price is AED 324
AED 362 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Great stay!"
United States
Ann
The price is AED 364
AED 406 total
includes taxes & fees
15 Dec - 16 Dec
The Yankee, Trademark Collection by Wyndham
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
The price is AED 320
AED 358 total
includes taxes & fees
1 Dec - 2 Dec
Quality Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
The price is AED 384
AED 422 total
includes taxes & fees
18 Nov - 19 Nov
Shaker Mill Inn
Room, 1 Queen Bed, 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, (787)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
Monument Mountain Motel
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, (558)
"I loved the stay people were nice loved the pool and internet was great "
United States
Jennifer
The price is AED 275
AED 308 total
includes taxes & fees
17 Nov - 18 Nov
Travelodge by Wyndham Great Barrington Berkshires
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, (1002)
"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 AED 403
AED 450 total
includes taxes & fees
7 Dec - 8 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2135)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is AED 382
AED 467 total
includes taxes & fees
17 Nov - 18 Nov
Vacation Village in the Berkshires
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (799)
"Easy parking, great community spaces, beautiful decor! "
United States
Kerry
The price is AED 340
AED 380 total
includes taxes & fees
17 Nov - 18 Nov
Berkshires Untold
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (823)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
17 Nov - 18 Nov
Howard Johnson by Wyndham Lenox
Free buffet breakfast
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

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

2.5 star property
Rensselaer
8.8 out of 10, Excellent, (850)
"Clean, quiet, and comfortable stay. The staff was polite and very helpful throughout my visit, and as a solo female traveler, I felt completely safe and at ease. I didn’t try the breakfast, but it looked and smelled great when I passed by. Would definitely stay again!"
United States
Brandi
The price is AED 349
AED 387 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (756)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1000)
"Nice and clean would stay again."
United States
Stephen
The price is AED 309
AED 345 total
includes taxes & fees
30 Nov - 1 Dec
Quality Inn
Lobby
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 star property
Castleton-on-Hudson
8.4 out of 10, Very Good, (1007)
"Room was spotless, staff very friendly."
United States
amber
The price is AED 387
AED 430 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites East Greenbush - Albany
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
The price is AED 496
AED 554 total
includes taxes & fees
23 Nov - 24 Nov
Element Lenox Berkshires
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway "
Leslie 4-night trip
Posted 1 day ago
Berkshire Mountain Lodge

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?
Our top-rated resort near Chatham: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 17.6 mi (28.4 km) from Chatham. Enjoy the sauna, fitness center, and terrace.
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.