Search Resort Hotels in Chatham from CA $90

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Recommended hotels in Chatham

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.
The price is CA $294
CA $492 total
includes taxes & fees
May 10 - May 11
Sugar Shack - 300 square feet of pure sweetness.

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.
The price is CA $335
CA $430 total
includes taxes & fees
May 11 - May 12
BLUSH: Boutique TINY home*private spa*walk to town

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.4 out of 10, Exceptional, (3 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is CA $242
CA $430 total
includes taxes & fees
May 11 - May 12
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is CA $150
CA $167 total
includes taxes & fees
May 13 - May 14
Best Western Plus Berkshire Hills Inn & Suites

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is CA $93
CA $104 total
includes taxes & fees
May 17 - May 18
Monument Mountain Motel

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 CA $82
CA $90 total
includes taxes & fees
May 31 - Jun 1
Pleasant Valley Motel West Stockbridge

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is CA $147
CA $161 total
includes taxes & fees
May 11 - May 12
Shaker Mill Inn

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (466 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is CA $90
CA $100 total
includes taxes & fees
May 11 - May 12
Berkshire Travel Lodge

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, (219 reviews)
"Everything was great we can’t wait to return !"
United States
Diana
The price is CA $217
CA $294 total
includes taxes & fees
May 19 - May 20
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is CA $116
CA $129 total
includes taxes & fees
May 12 - May 13
Quality Inn Great Barrington

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is CA $155
CA $173 total
includes taxes & fees
May 10 - May 11
Berkshires Untold

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is CA $120
CA $164 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is CA $122
CA $136 total
includes taxes & fees
May 10 - May 11
The Yankee Inn

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (578 reviews)
"Clean"
United States
Brian
The price is CA $102
CA $114 total
includes taxes & fees
May 13 - May 14
Travelodge by Wyndham Great Barrington Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is CA $150
CA $168 total
includes taxes & fees
May 27 - May 28
The Little Lion

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (94 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is CA $150
CA $167 total
includes taxes & fees
May 12 - May 13
Gregory House Country Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
"Great value"
United States
Ralph
The price is CA $108
CA $120 total
includes taxes & fees
May 10 - May 11
Howard Johnson by Wyndham Lenox

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.0 out of 10, Very good, (120 reviews)
"Clean rooms! Excellent staff"
United States
Travis
The price is CA $144
CA $156 total
includes taxes & fees
Jun 7 - Jun 8
Spark by Hilton West Coxsackie

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (142 reviews)
"Nice spacious room & bathroom with everything I needed. Staff was very helpful."
United States
Caitlin
The price is CA $169
CA $191 total
includes taxes & fees
May 14 - May 15
Howard Hotel

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
United States
Edith
The price is CA $151
CA $168 total
includes taxes & fees
May 19 - May 20
Quality Inn Lee - Lenox South
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

Find out more about Chatham

Chatham Resorts information

Number of reviews
11,220
Accommodation
29 Resorts
Lowest Price
CA $90
Highest Price
CA $492

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 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.

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