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Check availability on Chatham Pet-Friendly Hotels

Our top choices for Chatham pet-friendly hotels

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Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ₹11,838
₹13,223 total
includes taxes & fees
22 Dec - 23 Dec
Element Lenox Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is ₹9,752
₹10,698 total
includes taxes & fees
14 Dec - 15 Dec
Shaker Mill Inn
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (188)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is ₹12,651
₹14,170 total
includes taxes & fees
16 Dec - 17 Dec
the Alander
Mini-fridge, stovetop, cookware/dishes/utensils, paper towels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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, (107)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is ₹10,754
₹15,518 total
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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

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 ₹8,521
₹9,518 total
includes taxes & fees
6 Jan - 7 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (1000)
"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 ₹9,145
₹10,215 total
includes taxes & fees
22 Dec - 23 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk
Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is ₹13,555
₹15,182 total
includes taxes & fees
14 Dec - 15 Dec
Changing Times Boutique Country Lodging
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ₹9,940
₹11,103 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Little Lion
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (986)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₹8,377
₹9,357 total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Great staff especially Katherine "
michael 3-night trip
Posted 7 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the ambience - historic and comfortable and excellent food. "
Nancy 1-night trip
Posted 1 month ago
The Red Lion Inn

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Frequently asked questions

What's the best time of year to travel to Chatham with my pet?
When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to see and do with your pet in Chatham?
Known for its theatres, Chatham has lots to offer visitors. See the local sights and visit The Mac-Haydn Theatre. When you're in the area, make time for a stop at Martin Van Buren National Historic Site.