Pet Friendly Hotels & Resorts in Cheshire from AU$128

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Check availability on Cheshire Pet Friendly Hotels

Our top choices for Cheshire pet-friendly hotels

Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
The price is AU$220
includes taxes & fees
21 Dec - 22 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 AU$177
includes taxes & fees
17 Dec - 18 Dec
Shaker Mill Inn
Exterior
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 AU$168
includes taxes & fees
4 Jan - 5 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby sitting area
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, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is AU$128
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
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, (988)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AU$156
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Courtyard
The Springs Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (88)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is AU$177
includes taxes & fees
16 Dec - 17 Dec
The Springs Motel
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AU$150
includes taxes & fees
16 Dec - 17 Dec
The Central Downtown Inn & Suites
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (816)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is AU$184
includes taxes & fees
16 Dec - 17 Dec
Berkshires Untold
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (589)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is AU$166
includes taxes & fees
16 Dec - 17 Dec
Maple Terrace Motel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is AU$181
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
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 Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We had a very nice experience staying at the Red Lion Inn. Our room was upgraded when checking in which was a nice surprise. The hotel was beautifully decorated for the season. We loved the cozy feel of the fireplace in the lobby especially on such a cold day. "
Sandra 1-night trip
Posted 3 days ago
The Red Lion Inn

Frequently asked questions

What's the best time of year to travel to Cheshire with my pet?
When you travel with your pet, keeping track of the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What is there to see and do with your pet in Cheshire?
Known for its skiing, Cheshire has lots to offer visitors, including its hiking trails and natural beauty. See the local sights and visit Mount Greylock State Reservation. When you're in the area, make time for a stop at Mount Greylock State Reservation Visitor Center.

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