Pet Friendly Hotels & Resorts in Chester from NZ$212

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Our top choices for Chester pet-friendly hotels

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 NZ$574
includes taxes & fees
20 Jan - 21 Jan 2026
Chester Farmhouse Ski Retreat near Slopes

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

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 NZ$254
includes taxes & fees
7 Jan - 8 Jan 2026
Sleep Woodstock Motel

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 NZ$248
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway Inn Mt. Snow

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

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 NZ$231
includes taxes & fees
28 Dec - 29 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

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

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 NZ$287
includes taxes & fees
7 Jan - 8 Jan 2026
Best Western Springfield Hotel

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 NZ$277
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn Brattleboro

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 NZ$212
includes taxes & fees
7 Jan - 8 Jan 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.

Top Chester Hotel Reviews

Frequently asked questions

What's the best dog-friendly place to stay in Chester?
Motel in the Meadow is a top dog-friendly option for your stay. Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub is another good option for a stay with your pet.
How many dog-friendly hotels are there in Chester?
Enjoy travelling with your furry pal at one of Expedia's 5 dog-friendly Chester hotels or accommodation options.
What's the best time of year to travel to Chester with my pet?
When you're travelling 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm 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 Okemo Mountain Resort.