A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check availability on Chester Pet-friendly Hotels

Tonight
Aug 9 - Aug 10
Tomorrow
Aug 10 - Aug 11
Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23

Our top choices for Chester pet-friendly hotels

Dining
Dining
Exterior
Living area

1. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
United States
Stephanie F.
￥31,236
￥64,492 total
includes taxes & fees
Aug 11 - Aug 12
Charming Chester Farmhouse near Near VT Slopes
Exterior
Smart TV, fireplace
Smart TV, fireplace
Smart TV, fireplace

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
United States
Lorraine C.
￥44,173
￥101,068 total
includes taxes & fees
Aug 17 - Aug 18
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Exterior
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds (surcharge)
Free daily buffet breakfast
Indoor pool

3. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
￥28,256
￥31,082 total
includes taxes & fees
Aug 17 - Aug 18
Best Western Springfield Hotel
Restaurant
Bar (on property)
Interior
Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly | 1 bedroom, desk, iron/ironing board (on request), WiFi (free)

4. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Bradley
￥13,722
￥15,231 total
includes taxes & fees
Sep 1 - Sep 2
The Upper Pass Lodge at Magic Mountain
Lounge
Sundeck
Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed | Premium bedding, WiFi (free), individually decorated
Interior entrance

5. Bromley View Inn

Bromley View Inn
Bondville
United States
Josh
￥12,062
￥13,267 total
includes taxes & fees
Aug 10 - Aug 11
Bromley View Inn
Exterior
Property grounds
Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds (surcharge), WiFi (free)
Exterior

6. The Putney Inn

The Putney Inn
Putney
United States
Robert
￥19,523
￥21,475 total
includes taxes & fees
Aug 10 - Aug 11
The Putney Inn
Exterior
2 bedrooms, iron/ironing board, WiFi (free), bed sheets
Interior
Dining

7. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
￥26,819
￥57,601 total
includes taxes & fees
Aug 10 - Aug 11
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Lobby
Suite, 1 King Bed with Sofa bed | Desk, blackout drapes, iron/ironing board, WiFi (free)
Property grounds
Interior

8. Colonial Motel

Colonial Motel
Brattleboro
United States
James
￥11,784
￥12,963 total
includes taxes & fees
Aug 10 - Aug 11
Colonial Motel
Indoor pool
Lobby
Free breakfast
Restaurant

9. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Kyle
￥19,275
￥21,203 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn Brattleboro
Lobby
Standard Room, 1 King Bed, Non Smoking | In-room safe, desk, iron/ironing board, cribs (free)
Indoor pool
Fitness facility

10. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Ramica
￥17,275
￥18,742 total
includes taxes & fees
Sep 2 - Sep 3
Keene Elm City Hotel, an Ascend Collection Hotel
View all properties

Top Chester Hotel Reviews

Latchis Hotel

Latchis Hotel

8/10 Good
"Excellent location"
Stark 1-night trip
Posted 2 hours ago
Latchis Hotel
Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"The property looks newly refurbished. Everything was in excellent shape, and the grounds were quite nice. And very clean. Also pet friendly. Would definitely recommend!"
Wayne 1-night trip
Posted 22 hours ago
Sleep Woodstock Motel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"As always, this place never disappoints. From the friendly staff that greets you at check-in, to the breakfast buffet that gives you a good variety to start your day… this will always be my go-to when visiting Keene."
Patrick 1-night trip
Posted 1 day ago
Keene Elm City Hotel, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"Kind personnel, large green area. Breakfast is too basic though."
Alex 2-night trip
Posted 1 day ago
Colonial Motel
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 2 days ago
Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

8/10 Good
"Good place to stay, but not great."
Sean 2-night trip
Posted 5 days ago
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Yvette 1-night trip
Posted 6 days ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

What's the best pet-friendly place to stay in Chester?
Restorative Mountain Sanctuary with Hot Tub, Minutes from the Mountains is a top pet-friendly option for your stay. Motel in the Meadow is another good choice for you and your pet.
How many hotels that welcome pets will I find in Chester?
Frolic with your furry friend at one of Expedia's 5 Chester hotels that allow pets.
What's the best time of year to travel to Chester with my pet?
When you're traveling with pets, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to see and do with your pet in Chester?
Known for its hiking trails, Chester has lots to offer visitors including its skiing and mountains. See the local sights and visit DaVallia Art & Accents and Bonnie's Bundles Dolls. When you're in the area, make time for a stop at Vermont Country Store.

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