Best Resorts in Chatham

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Nov 14 - Nov 16
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Dec 5 - Dec 7
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Resorts in Chatham

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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
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.
$303 nightly
The price is $342
Nov 5 - Nov 6
Total with taxes and fees
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
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.
$303 nightly
The price is $342
Nov 4 - Nov 5
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Smart TV, fireplace
HunnyHAUS: Deluxe TINY*private spa*walk to town
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...
United States
Megan H.
$366 nightly
The price is $413
Nov 16 - Nov 17
Total with taxes and fees
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
8.6 out of 10, Excellent, (1024)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$93 nightly
The price is $104
Nov 6 - Nov 7
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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
9.0 out of 10, Wonderful, (782)
"This was an older property, but room was nice and bathroom was updated. "
United States
Martha
$67 nightly
The price is $74
Nov 4 - Nov 5
Total with taxes and fees
Monument Mountain Motel
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (433)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
$105 nightly
The price is $116
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (939)
"Enjoyable stay. Staff were very nice. "
United States
Claire
$103 nightly
The price is $115
Nov 6 - Nov 7
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (745)
"Great stay, perfect "
United States
Lawrence
$113 nightly
The price is $126
Nov 4 - Nov 5
Total with taxes and fees
Berkshire Mountain Lodge
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (688)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
$107 nightly
The price is $120
Nov 30 - Dec 1
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very Good, (1003)
"Nice and clean would stay again."
United States
Stephen
$84 nightly
The price is $94
Nov 17 - Nov 18
Total with taxes and fees
Quality Inn
Exterior
Fairfield Inn & Suites Albany East Greenbush
Fairfield Inn & Suites Albany East Greenbush
2.5 star property
8.6 out of 10, Excellent, (1013)
"Nice motel and easy to get to."
United States
lucille
$101 nightly
The price is $112
Dec 4 - Dec 5
Total with taxes and fees
Fairfield Inn & Suites Albany East Greenbush
Exterior
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.6 out of 10, Exceptional, (9)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 13 - Nov 14
Total with taxes and fees
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1007)
"We had a lakeside room which was wonderful!"
United States
Nancy
$110 nightly
The price is $122
Nov 12 - Nov 13
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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
7.6 out of 10, Good, (556)
"Excellent location, friendly service, clean, comfortable room."
United States
Beth
$75 nightly
The price is $84
Nov 4 - Nov 5
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8 out of 10, (1001)
"good average place to stay."
United States
Terry
$58 nightly
The price is $64
Nov 19 - Nov 20
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Exterior
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (818)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 4 - Nov 5
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Premium bedding, memory foam beds, individually decorated
Nautical Nest
Nautical Nest
2.5 star property
9.6 out of 10, Exceptional, (121)
"It was really nice and the location was great. Michael was a good host."
United States
Pamela
$110 nightly
The price is $124
Nov 4 - Nov 5
Total with taxes and fees
Nautical Nest
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1028)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
$118 nightly
The price is $132
Nov 11 - Nov 12
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
BBQ/picnic area
Hampton Inn & Suites Albany-East Greenbush
Hampton Inn & Suites Albany-East Greenbush
2.5 star property
9.0 out of 10, Wonderful, (863)
"Overall experience was exceptional. "
United States
Daniel
$118 nightly
The price is $135
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn & Suites Albany-East Greenbush
Lobby
Quality Inn
Quality Inn
2.5 star property
8.4 out of 10, Very Good, (1010)
"Fine lodging for short term business stay"
United States
Lawrence
$93 nightly
The price is $104
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn
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

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

10/10 Excellent
"The lady in the cafeteria/ breakfast section and the night receptionist were very pleasant 😊"
Careene 2-night trip
Posted 23 hours ago
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Find out more about Chatham

Chatham Resorts information

Number of reviews
13,008
Accommodation
32 Resorts
Lowest Price
$64
Highest Price
$413

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 highest-rated resort near Chatham: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 17.6 mi (28.4 km) from Chatham. Amenities include a sauna, a fitness center, and a 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 Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site.
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.

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