Find Pet-friendly Hotels in Chester, VT

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Pick from 25 Chester Pet-friendly Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Stunning farmhouse-Historic village-Mins to Skiing
2nd floor bedroom with two twin beds and second office desk

Stunning farmhouse-Historic village-Mins to Skiing

9.2 out of 10, Wonderful, (10)
"Fantastic house, everything was perfect, great communication with owner"
Stunning farmhouse-Historic village-Mins to Skiing
Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Aerial view

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

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Motel in the Meadow
Exterior

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
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Exterior

Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub

10.0 out of 10, Exceptional, (1)
"Went to Vermont with another family (4 adults, 4 children). The house was just the right size for us and looked mostly like the pictures. Pros: 1) Super cute rustic home but well renovated to keep the charm with modern touches. 2) The place is well cleaned and comfortable with books, games and puzzles. 3) The kitchen is very well stocked with everything we could need. 4) Beds were clean and comfortable. 5) Bathrooms spacious and clean. 6)The yard has so much to offer with a lovely deck...
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Historic Farmhouse, Quaint Vermont Experience
Marie Hill Farmhouse

Historic Farmhouse, Quaint Vermont Experience

10.0 out of 10, Exceptional, (16)
"The property and house were beautiful. Very spacious rooms with comfortable beds. Kristen was very responsive and lovely to have met when we arrived. Great location and easy to find. Hope to be able to stay here again in the future! "
Historic Farmhouse, Quaint Vermont Experience
Charming Chester Farmhouse – peaceful and close to everything!
Property grounds

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (7)
"The house has been well renovated and is very nice and well situated within walking distance to coffee house and main street. The owner is nice. But, if you are going there during hot summer days, there is only one very small and inefficient AC in one of the bedrooms and the rest of the bedrooms have fans but we were a group a 5 adults and none us had a good night sleep. Even if the air was cooler outside, it just didn't come in and it was way too hot and humid in the bedrooms and the fans...
The price is SAR 544
SAR 1,291 total
includes taxes & fees
25 Nov - 26 Nov
Charming Chester Farmhouse – peaceful and close to everything!
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Chester Vacation Rental | 5BR | 2BA | Stairs Required | 3,000 Sq Ft

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

9.8 out of 10, Exceptional, (47)
"Lovely house on beautiful property. We thoroughly enjoyed staying at Smokeshire Farm. We will never forget the moon rising over the hill or being greeted by the sheep in the morning."
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (6)
"This property was exactly as pictured and the owner was quick in communicating with us in both getting needed information to us and responding to any concerns we had. We enjoyed looking up the history of the cottage's stone work and everything about our stay here and in this lovely town. Very charming and well maintained property. We look forward to possibly staying here again if our future travels bring us back through Chester, VT. "
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Living area

UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!

9.2 out of 10, Wonderful, (5)
"We had a great time skiing, both Killington and Okemo are close, and staying at this clean and spacious vrbo. We were parents with two teenage sons, two girlfiends and a dog. The space worked really well. Sitting in the hot tub at night under the stars was wonderful."
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Ski Okemo, Killington, Magic & Bromley
Exterior

Ski Okemo, Killington, Magic & Bromley

10.0 out of 10, Exceptional, (9)
"My adult children and I spent Labor Day weekend working on a building project in Chester. This home was just what we needed -convenient location, 4 bedrooms set up for couples, a very serviceable kitchen (we prefer to cook for each other), solid WiFi, and a private restful outdoor space. We would definitely stay there again!"
Ski Okemo, Killington, Magic & Bromley
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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Frequently asked questions

What's the best pet-friendly place to stay in Chester?
Stunning farmhouse-Historic village-Mins to Skiing is a top pet-friendly option for your stay. Two other good options to stay with your pet include Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR and Motel in the Meadow.
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 Okemo Mountain Resort.