Find pet-friendly hotels in Chatham, NY from $103

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Top Chatham Pet-friendly Hotels

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 11 - Dec 12
Total with taxes and fees
Element Lenox Berkshires

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Shaker Mill Inn

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1005)
"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
Dec 7 - Dec 8
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (976)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1001)
"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
$101 nightly
The price is $113
Dec 14 - Dec 15
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
$114 nightly
The price is $127
Dec 7 - Dec 8
Total with taxes and fees
Berkshires Untold

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$169 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Red Lion Inn

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
$110 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Little Lion

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$247 nightly
The price is $276
Jan 4 - Jan 5, 2026
Total with taxes and fees
Prospect 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.

Find out more about Chatham

Discover top Chatham attractions with your pet

Chatham, New York, is a delightful spot for travelers who want to bring their furry companions along for the adventure. Start your day at the scenic Chatham Town Park, where you and your pet can stroll through lush green spaces and enjoy the fresh air while taking in views of the nearby hills. For a taste of local culture, visit the Chatham Historical Society Museum, where you can learn about the area's rich heritage—some outdoor exhibits allow you to explore with your pet by your side. Don’t miss a trip to the nearby Taconic State Park, featuring miles of trails perfect for hiking with your dog, offering both challenging and easy paths amidst stunning natural beauty. After a day of exploration, unwind at one of the pet-friendly hotels situated downtown, where attentive service and cozy accommodations await. Many of these hotels provide easy access to local shops and restaurants, ensuring you and your pet can enjoy the vibrant community while having a comfortable retreat to relax in after a day of adventure.

Top Chatham Hotel Reviews

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 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 is there to see and do with your pet in Chatham?
Known for its theaters, 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.

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