An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

Pet Friendly Hotels & Resorts in Cheshire from AU$110

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Check availability on Cheshire Pet Friendly Hotels

Our top choices for Cheshire pet-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is AU$193
includes taxes & fees
29 June - 30 June
Best Western Plus Berkshire Hills Inn & Suites
Property grounds

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
The price is AU$198
includes taxes & fees
25 June - 26 June
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
1 bedroom, free WiFi, bed sheets

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is AU$288
includes taxes & fees
9 July - 10 July
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Courtyard

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (102 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is AU$168
includes taxes & fees
25 June - 26 June
The Springs Motel
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"Clean room and breakfast"
United States
Raphael
The price is AU$283
includes taxes & fees
1 July - 2 July
The Red Lion Inn
View from property

Williamstown Motel

Williamstown Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (327 reviews)
"Clean rooms and the staff was extremely friendly and helpful"
United States
Graham
The price is AU$144
includes taxes & fees
30 June - 1 July
Williamstown Motel
Property grounds

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,001 reviews)
"The property was nice and the staff enthusiastic"
United States
Matt
The price is AU$149
includes taxes & fees
2 July - 3 July
Willows Motel Williamstown
Standard Room, 1 King Bed, Non Smoking

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (250 reviews)
"Had a great stay."
United States
Trevor
The price is AU$110
includes taxes & fees
23 July - 24 July
Rodeway Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AU$271
includes taxes & fees
1 July - 2 July
Shaker Mill Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (112 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is AU$276
includes taxes & fees
6 July - 7 July
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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

Hotel On North

Hotel On North

10/10 Excellent
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."
David 1-night trip
Posted 4 hours 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 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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