A lake surrounded by autumn-colored trees and hills.

Pet Friendly Hotels & Resorts in Cheshire from AU$107

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Check availability on Cheshire Pet Friendly Hotels

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Cheshire pet-friendly hotels

A patio area with outdoor furniture, a fire pit, and potted plants.
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A cozy living room with a stone fireplace, comfortable seating, and a television.

1. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AU$165
includes taxes & fees
1 Nov - 2 Nov
The Springs Motel
A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.
A single-story building with a porch, a chimney, and a satellite dish.
A room with a door, a table with a chair, a window with blinds, and an air conditioning unit.
A reception desk with a computer, a monitor, and a sign about Choice Privileges.

2. Rodeway Inn

Rodeway Inn
Adams
United States
Joann
AU$107
includes taxes & fees
3 Nov - 4 Nov
Rodeway Inn
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern interior with a large window, a wooden table, and bar stools.
A modern hotel building with the name "Hotel Downtown" on the facade.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

3. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
mary ellen
AU$190
includes taxes & fees
11 Nov - 12 Nov
Hotel Downstreet, an Ascend Collection Hotel
A patio area with wooden chairs and tables, surrounded by dense greenery and trees.
A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.
A hotel room with a TV, a desk, a chair, a dresser, a bed with a patterned bedspread, and a microwave.
A hay bale display with pumpkins and scarecrows.

4. Willows Motel Williamstown

Willows Motel Williamstown
Williamstown
United States
David
AU$134
includes taxes & fees
3 Nov - 4 Nov
Willows Motel Williamstown
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.
A living room with a sofa, coffee table, and fireplace. There is a kitchen area with cabinets and a refrigerator.
A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

5. Williamstown Motel

Williamstown Motel
Williamstown
United States
Ahmet
AU$115
includes taxes & fees
3 Nov - 4 Nov
Williamstown Motel
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Debra
AU$157
includes taxes & fees
25 Oct - 26 Oct
The Central Downtown Inn & Suites
A building entrance with a large planter with purple flowers and a small tree.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A library with bookshelves, a television, and two armchairs.

7. Hotel On North

Hotel On North
Pittsfield
United States
Devon
AU$199
includes taxes & fees
22 Nov - 23 Nov
Hotel On North
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

8. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
James
AU$155
includes taxes & fees
15 Nov - 16 Nov
Best Western Plus Berkshire Hills Inn & Suites
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ginger
AU$157
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A wooden cabinet with a coffee maker and a white container.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
AU$174
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn & Suites Berkshires-Lenox
View all properties

Top Cheshire Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 1 day ago
Hotel On North
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 7 days 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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