Chester Pet-friendly Hotel

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chester Pet-friendly Hotel

Top Chester Pet-friendly Hotel

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
Smart TV, fireplace, books, stereo

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
Interior

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
Chester Farmhouse Ski Retreat near Slopes
Terrace/patio

Chester Farmhouse Ski Retreat near Slopes

9.6 out of 10, Exceptional, (14)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is HK$1,516
HK$3,152 total
includes taxes & fees
21 Oct - 22 Oct
Chester Farmhouse Ski Retreat near Slopes
Spacious 5-bedroom cabin in charming Chester
Microwave, oven, stovetop, dishwasher

Spacious 5-bedroom cabin in charming Chester

Spacious 5-bedroom cabin in charming Chester
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (17)
"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Dining

UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!

9.2 out of 10, Wonderful, (5)
"The beautiful living room was warm and inviting and made for a perfect relaxation spot after a great day of skiing!"
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Historic Farmhouse, Quaint Vermont Experience
Exterior

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
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Interior

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
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.
View all properties

Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"."
Rachel 1-night trip
Posted 3 days ago
The Shire Woodstock

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 DaVallia Art & Accents and Bonnie's Bundles Dolls. When you're in the area, make time for a stop at Vermont Museum of Mining and Minerals.