Find Pet-friendly Hotels in Chester, VT

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Compare Chester Pet-friendly Hotels 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, (2)
"During this season of gratitude we felt so lucky to stay at such a well appointed and lovely home. Unlike many rental homes that are stripped of personality, this home was full of charm and lovingly designed touches. From the cookware to the bedding the home was welcoming and comfortable. The kitchen and living room in particular were of good size for our entire group to eat and relax comfortably each with its own fireplace. "
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Historic Farmhouse, Close to Skiing
Marie Hill Farmhouse

Historic Farmhouse, Close to Skiing

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, Close to Skiing
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 826
SAR 1,657 total
includes taxes & fees
8 Jan - 9 January 2025
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, (7)
"Everything was wonderful from the very beginning… The ease of booking, payment, check-in, property, check out, it was all perfect! The house was in a great neighborhood, very quaint, and just the perfect size for the six of us. Well maintained and clean, had everything we could possibly need. Highly recommend."
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!!
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Outdoor dining

Cozy 4bd - 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!"
Cozy 4bd - 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 Vermont Country Store.