Chester Hotel Guide - Pet Friendly Hotels in Chester, Vermont

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Check availability on Chester Pet Friendly Hotels

Top Chester Pet Friendly Hotels

Motel in the Meadow
Welcome to Motel in the Meadow, a peaceful retreat.

Motel in the Meadow

2.5 star property
8.4 out of 10, Very good, (71)
"Cute little motel. Basic but has what you need. Yummy muffins for breakfast too."
Motel in the Meadow
Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Enjoy a panoramic view of the lush landscape from this cozy room with a central wood-burning fireplace and natural surroundings.

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Relax in this inviting living room with a comfortable sofa, fireplace, and flat-screen TV.

Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub

10.0 out of 10, Exceptional, (3)
"We loved staying in Amelia’s wonderful home! It was a short 20 min from Okemo ski resort and provided all of features we needed. Thank you for everything and for being so attentive!"
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Experience the airy atmosphere of this room with a high ceiling and large skylight, offering a view of the outdoors.

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Charming Chester Farmhouse – peaceful and close to everything!
Relax in the serene outdoor seating area surrounded by lush greenery and vibrant flowers.

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (11)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is €382
includes taxes & fees
4 Aug - 5 Aug
Charming Chester Farmhouse – peaceful and close to everything!
Historic Farmhouse, Quaint Vermont Experience
Situated in a lush landscape, this rustic barn features a large open doorway and a smaller window.

Historic Farmhouse, Quaint Vermont Experience

10.0 out of 10, Exceptional, (19)
"We had a wonderful ski weekend with our family and the accommodations were excellent. "
Historic Farmhouse, Quaint Vermont Experience
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Relax in the cottage's outdoor seating area, featuring a wicker chair, cushioned bench, and small table.

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (12)
"We started 2 nights while skiing at Okemo. It was a nice warm cozy spot to relax at the end of the day. Loved that it's a historic stone structure as well. Not to mention the covered bridge that you drive through on the way! "
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Enjoy cooking in this kitchen with a window offering a view of lush greenery.

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Amazing stay! Close to Okemo and downtown!"
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Enjoy cooking in this kitchen with a window view of lush greenery.

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Sage House at Camp Greenwood Vermont with Sauna
Stylish interior with a central staircase, loft area, and natural light pouring in through the window.

Sage House at Camp Greenwood Vermont with Sauna

10.0 out of 10, Exceptional, (3)
"I had a great stay, kitchen is fully equipped. The place is clean and cozy. My dtay was very relaxing. Would definitely stay again."
Sage House at Camp Greenwood Vermont with Sauna
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.

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. Two other good options for you and your pet include Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR and Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub.
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 DaVallia Art & Accents and Bonnie's Bundles Dolls. When you're in the area, make time for a stop at Vermont Country Store.