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Find Pet-friendly Hotels in Cheshire, MA

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Check availability on Cheshire Pet-friendly Hotels

Tonight
Oct 31 - Nov 1
Tomorrow
Nov 1 - Nov 2
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Top Cheshire Pet-friendly Hotels

Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (432)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
The price is NT$3,347
NT$3,672 total
includes taxes & fees
Nov 3 - Nov 4
Shaker Mill Inn
Exterior
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.6 out of 10, Exceptional, (9)
"New hotel very nice"
United States
joel
The price is NT$4,131
NT$4,614 total
includes taxes & fees
Nov 9 - Nov 10
Element Lenox Berkshires
Non Lakeside Superior Room, 2 Queen beds | Premium bedding, desk, laptop workspace, blackout drapes
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is NT$3,251
NT$3,632 total
includes taxes & fees
Nov 6 - Nov 7
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard
The Springs Motel
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (83)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
The price is NT$3,135
NT$3,440 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.6 out of 10, Excellent, (1022)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is NT$2,860
NT$3,195 total
includes taxes & fees
Nov 4 - Nov 5
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (934)
"Friendly staff and clean rooms. Loved the onsite restaurant & bar."
United States
Carmen
The price is NT$3,152
NT$3,521 total
includes taxes & fees
Nov 7 - Nov 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (787)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is NT$2,835
NT$3,167 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
Exterior
Willows Motel Williamstown
Willows Motel Williamstown
2.0 star property
9.0 out of 10, Wonderful, (975)
"Br and rooms were cleaneakfast was excellent"
United States
Joseph
The price is NT$2,726
NT$3,046 total
includes taxes & fees
Nov 2 - Nov 3
Willows Motel Williamstown
Front of property - evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (787)
"Clean room, great location. Restaurant phenomenal "
United States
Mary
The price is NT$4,082
NT$4,559 total
includes taxes & fees
Nov 3 - Nov 4
Hotel On North
Exterior detail
Maple Terrace Motel
Maple Terrace Motel
2.5 star property
9.6 out of 10, Exceptional, (581)
"Excellent place. Bountiful view. "
United States
Tania
The price is NT$3,029
NT$3,384 total
includes taxes & fees
Nov 2 - Nov 3
Maple Terrace Motel
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.
View all properties

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Clean room and very friendly staff. "
Michael 2-night trip
Posted 10 hours ago
The Red Lion Inn

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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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire 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 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.