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Our top choices for Chester pet-friendly hotels

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (6)
"Clean rooms/ close to mountain/ nice experience"
United States
Morgan
The price is ฿4,194
฿4,614 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hideaway Inn Mt. Snow

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, (550)
"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 ฿2,427
฿4,609 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel

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, (969)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is ฿3,848
฿4,175 total
includes taxes & fees
30 Dec - 31 Dec
Keene Elm City Hotel, an Ascend Collection Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (808)
"The staff were very friendly; the breakfast was awesome. the pool was heated just right, and the room was very clean, I will stay here again. Good job Best western,"
United States
Jose
The price is ฿4,721
฿5,193 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (16)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (840)
"Great stay"
United States
Jason
The price is ฿3,910
฿4,301 total
includes taxes & fees
30 Dec - 31 Dec
Latchis 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 ฿4,555
฿5,011 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Brattleboro
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.
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.