Aerial scene of Chatham, Ontario, Canada

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Recommended hotels in Chatham

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 $354
CA $452 total
includes taxes & fees
Jun 29 - Jun 30
BLUSH: Boutique TINY home*private spa*walk to town

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is CA $314
CA $759 total
includes taxes & fees
Jun 24 - Jun 25
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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 $318
CA $527 total
includes taxes & fees
Jun 28 - Jun 29
Sugar Shack - 300 square feet of pure sweetness.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is CA $326
CA $542 total
includes taxes & fees
Jul 1 - Jul 2
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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is CA $169
CA $188 total
includes taxes & fees
Jun 29 - Jun 30
Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is CA $203
CA $226 total
includes taxes & fees
Jul 7 - Jul 8
The Yankee Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is CA $102
CA $112 total
includes taxes & fees
Jun 25 - Jun 26
Pleasant Valley Motel West Stockbridge

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,012 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is CA $154
CA $172 total
includes taxes & fees
Jun 24 - Jun 25
Quality Inn Great Barrington

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is CA $249
CA $273 total
includes taxes & fees
Jul 1 - Jul 2
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (873 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is CA $157
CA $176 total
includes taxes & fees
Jul 19 - Jul 20
Monument Mountain Motel

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, (249 reviews)
"Really great location and near great area."
United States
Sherwin
The price is CA $282
CA $365 total
includes taxes & fees
Jul 6 - Jul 7
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is CA $96
CA $107 total
includes taxes & fees
Jul 1 - Jul 2
Berkshire Travel Lodge

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (829 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is CA $82
CA $91 total
includes taxes & fees
Jun 25 - Jun 26
FairBridge Inn Express

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is CA $209
CA $234 total
includes taxes & fees
Jun 24 - Jun 25
Wilder House Berkshires

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (105 reviews)
"Wonderful stay! Our room was beautiful - clean and cozy. I had a drink at the outside bar - it was lovely. Highly recommend staying here. It’s a hidden gem."
United States
Michelle
The price is CA $159
CA $177 total
includes taxes & fees
Jun 24 - Jun 25
Gregory House Country Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (111 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is CA $242
CA $270 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.0 out of 10, Very good, (137 reviews)
"Nice friendly staff, offers Continental breakfast, clean facility and affordable pricing- definitely recommended!"
United States
Juan
The price is CA $138
CA $149 total
includes taxes & fees
Jul 7 - Jul 8
Spark by Hilton West Coxsackie

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)
"It was a clean, friendly hotel."
United States
Cheri
The price is CA $189
CA $212 total
includes taxes & fees
Jul 7 - Jul 8
Quality Inn Lee - Lenox South

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (587 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is CA $112
CA $125 total
includes taxes & fees
Jun 24 - Jun 25
Travelodge by Wyndham Great Barrington Berkshires

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (228 reviews)
"It’s a wonderful place to rest for a while. it has all you need, everything it’s in good conditions also it’s near of many activities like hiking."
United States
Daniel
The price is CA $241
CA $269 total
includes taxes & fees
Jul 9 - Jul 10
the Alander
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
9,150
Accommodation
28 Resorts
Lowest Price
CA $91
Highest Price
CA $759

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's our top-rated resort near Chatham: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 17.6 mi (28.4 km) from Chatham. Has 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 Queechy 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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