Photo by Ed Gaffny

Find Pet-friendly Hotels in Cheshire, MA from CA $88

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Check availability on Cheshire Pet-friendly Hotels

Tonight
Aug 2 - Aug 3
Tomorrow
Aug 3 - Aug 4
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Cheshire Pet-friendly Hotels

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Enjoy al fresco dining and socializing on this tranquil outdoor deck, complete with a barbecue grill and comfortable seating.

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here. Location was excellent. Very peaceful and quiet. The house was clean and had everything you needed. Would come again!"
The price is CA $225
CA $553 total
includes taxes & fees
Aug 5 - Aug 6
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
Interior

The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

The price is CA $306
CA $607 total
includes taxes & fees
Sep 1 - Sep 2
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
Hotel Downstreet, Ascend Hotel Collection
Two single beds with white linens and blue accents, accompanied by bedside tables and lamps, offer a functional workspace.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Clean,friendly staff and great location."
The price is CA $198
CA $221 total
includes taxes & fees
Sep 1 - Sep 2
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Traditional buildings with welcoming front porches and easy street access.

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (402)
"Very comfortable room that worked great for our family. "
The price is CA $257
CA $317 total
includes taxes & fees
Sep 2 - Sep 3
The Porches Inn at Mass MoCA
Pilgrim Inn
Enjoy meals in the dining area with a round table and comfortable seating.

Pilgrim Inn

2.5 star property
5.8 out of 10, (311)
"Great location but no staff at check-in or checkout!"
The price is CA $108
CA $121 total
includes taxes & fees
Aug 24 - Aug 25
Pilgrim Inn
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $620
CA $1,144 total
includes taxes & fees
Aug 11 - Aug 12
Spacious 5-bedroom house in charming Lee with WiFi
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is CA $88
CA $98 total
includes taxes & fees
Aug 17 - Aug 18
Econo Lodge Lee - Great Barrington
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Enjoy meals in this kitchen with a central island, dining area, and large windows offering a view of the outdoors.

Sun Filled Lenox Retreat - Minutes to Tanglewood!

The price is CA $342
CA $738 total
includes taxes & fees
Sep 1 - Sep 2
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $383
CA $428 total
includes taxes & fees
Sep 1 - Sep 2
Devonfield Inn B&B
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

Hotel On North

Hotel On North

10/10 Excellent
"This hotel has a lot more character than chain places on the highway, and parking was easy in the lot behind the hotel. Staff was friendly and efficient, the rooms were large and well-decorated, and the restaurant on the ground floor was top-notch."
Hugh 1-night trip
Posted 1 day ago
Hotel On North

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 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.