A lake surrounded by autumn-colored trees and hills.

Pet Friendly Hotels & Resorts in Cheshire

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Check availability on Cheshire Pet Friendly Hotels

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Cheshire pet-friendly hotels

Courtyard
Honeymoon Suite, 1 King Bed, Patio
Cabin, 3 Bedrooms, Mountainside | Living area
Seasonal outdoor pool

1. The Springs Motel

The Springs Motel
New Ashford
United States
Shakeila
AU$240
includes taxes & fees
9 Sept - 10 Sept
The Springs Motel
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
Property amenity
In-room safe, desk, laptop workspace, blackout curtains
Exterior

2. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Jermaine
AU$180
includes taxes & fees
2 Sept - 3 Sept
Best Western Plus Berkshire Hills Inn & Suites
Hypo-allergenic bedding, desk, laptop workspace, blackout curtains
Exterior
Reception
Front of property

3. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
William
AU$220
includes taxes & fees
9 Sept - 10 Sept
Hotel Downstreet, an Ascend Collection Hotel
Exterior
Suite, 1 Bedroom | Living area
Free continental breakfast
Lobby

4. Berkshire Valley Inn

Berkshire Valley Inn
Williamstown
United States
DM
AU$263
includes taxes & fees
26 Aug - 27 Aug
Berkshire Valley Inn
Restaurant
Exterior
Meeting facility
Indoor pool

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
David
AU$201
includes taxes & fees
27 Aug - 28 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property grounds
Desk, iron/ironing board (on request), cots/infant beds, free WiFi
Property grounds
Exterior

6. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
Richard
AU$164
includes taxes & fees
27 Aug - 28 Aug
Willows Motel Williamstown
Property grounds
Front of property – evening/night
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Property grounds

7. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Christine
AU$198
includes taxes & fees
8 Sept - 9 Sept
Maple Terrace Motel
Property entrance
Lobby sitting area
Dining
Lobby

8. Hotel On North

Hotel On North
Pittsfield
United States
Dragana
AU$283
includes taxes & fees
7 Sept - 8 Sept
Hotel On North
Front of property – evening/night
Lobby
BBQ/picnic Area
Hallway

9. The Williams Inn

The Williams Inn
Williamstown
United States
Thomas
AU$375
includes taxes & fees
16 Aug - 17 Aug
The Williams Inn
Free daily buffet breakfast
Free daily buffet breakfast
Snack bar
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
AU$232
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn & Suites Berkshires-Lenox
View all properties

Top Cheshire Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
Melinda 1-night trip
Posted 14 hours ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
Myrna 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
Michelle 2-night trip
Posted 2 weeks ago
FairBridge Inn Express

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 Cheshire Reservoir. When you're in the area, make time for a stop at Mount Greylock State Reservation Visitor Center.

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