Photo by Ed Gaffny

Pet Friendly Hotels & Resorts in Cheshire

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Check availability on Cheshire Pet Friendly Hotels

Best Cheshire Pet Friendly Hotels

19th c. Barn in the Berkshires
Interior

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (90)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires
Berkshires Lakefront Retreat by Evergreen Home
Fridge, microwave, oven, stovetop

Berkshires Lakefront Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Beautiful tranquil home base for a ski trip with friends. "
Berkshires Lakefront Retreat by Evergreen Home
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.

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Miranda at the front desk was beyond accommodating. My mom and I enjoyed our stay in this historic hotel!"
Elana 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 and St Mary's of the Assumption Church. When you're in the area, make time for a stop at Mount Greylock State Reservation Visitor Center.