Find Pet-friendly Hotels in Chester, VT

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Check availability on Chester Pet-friendly Hotels

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chester pet-friendly hotels

Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is ￥21,676
￥52,222 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Chester Farmhouse Ski Retreat near Slopes
Lounge
Bromley View Inn

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (406)
"Clean and great location with fun lounge area."
United States
Marshall
Bromley View Inn
Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is ￥12,210
￥23,190 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sleep Woodstock Motel
Interior
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (5)
"This was the perfect little getaway! Beautiful area, staff was nice, atmosphere was relaxing and having the hot tub option was perfect! "
United States
Harley
The price is ￥20,548
￥22,603 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Hideaway Inn Mt. Snow
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1001)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (968)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is ￥18,370
￥19,932 total
includes taxes & fees
Dec 28 - Dec 29
Keene Elm City Hotel, an Ascend Collection Hotel
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (15)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds, free WiFi
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is ￥23,720
￥26,093 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Best Western Springfield Hotel
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (928)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is ￥22,889
￥25,178 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Hampton Inn Brattleboro
Exclusive Suite, 3 Bedrooms, Kitchenette, Mountain View - Pet Friendly | 1 bedroom, desk, iron/ironing board, free WiFi
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very Good, (688)
"This place was a dream, everybody was so nice! We felt at home and safe."
United States
Gracie
The price is ￥17,366
￥19,275 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Upper Pass Lodge at Magic Mountain
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 Chester Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Comfort and cleanliness. Nice fireplace with comfortable couches. Very nice staff. Pretty Christmas decorations."
Nancy 2-night trip
Posted 7 days ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

What's the best pet-friendly place to stay in Chester?
Motel in the Meadow is a top pet-friendly option for your stay. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. When you're in the area, make time for a stop at Vermont Country Store.