Title: Book the Best PET FRIENDLY Hotels in Chester, VT from CA $168 - Chester Dog-Friendly Hotels | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) ![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Pet-friendly Hotels Tonight [Jan 17 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-17&endDate=2026-01-18&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-18&endDate=2026-01-19&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=PETS&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester pet-friendly hotels ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/97cdf1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/398175e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/2a2bd0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/69000000/68860000/68850200/68850104/13b3aaae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 4bd - Ski Okemo, Killington, Magic & Bromley [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) Chester 10/10 Exceptional (10 reviews) "We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla C. CA $506 CA $916 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/4ae7b7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/df792487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/95264663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/d409cd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse Ski Retreat near Slopes [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) Chester Depot 9.6/10 Exceptional (17 reviews) "This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori N. CA $221 CA $502 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c0073409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/4ee226d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c28fd1d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bromley View Inn [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) Bondville 9.0/10 Wonderful (412 reviews) "Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![Deluxe Suite | Private kitchen](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/9d3fcb33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/e57dec5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Electric vehicle charging station](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/0e4cb61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Woodstock Motel [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) Woodstock 9.6/10 Exceptional (555 reviews) "So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JILL CA $101 CA $198 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/286eff53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/67f64adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/w648h383x0y1-a98b9847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 8.8/10 Excellent (25 reviews) "Great cozy hotel very close to Mount Snow. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuhui CA $183 CA $202 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/7a5af75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0940a25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/017470f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) Keene 8.4/10 Very good (978 reviews) "Staff was very welcoming and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $167 CA $181 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/3973f8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/89435dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Putney Inn [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) Putney 8.4/10 Very good (1,000 reviews) "The room was okay for a quick stop to rest. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1023h453x0y0-571ad601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/ea836d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/24332bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1025h684x0y3-22b2c22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Columns Inn [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) Newfane 9.6/10 Exceptional (19 reviews) "Everything was great 👍 I will stay there again and highly recommend to others " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/f0e2c480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/8582bd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/67ba1eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) Springfield 8.8/10 Excellent (813 reviews) "Staff was so nice!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $211 CA $232 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/05d203e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/e3bf7119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/1bf7bbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2641a6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) Brattleboro 7.4/10 Good (478 reviews) "Room looked good. Wish they have shampoo. Only one soap. Nice shower pressure. Would visit again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miles CA $153 CA $168 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01®ionId=89014&adults=2&amenities=PETS&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg) ### The Manchester View 10/10 Excellent "Rooms were clean and they went above and beyond to check us in very early. I will definitely book again." [](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Beautiful area. The ground floor room was perfect!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! " [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Luxurious and friendly resort! Loved it" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Courteous staff Clean room" [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ## Frequently asked questions ### What are the most popular pet-friendly hotels in Chester? > Motel in the Meadow, with an 8.4 rating, welcomes pets to stay free of charge. Guests can also enjoy complimentary breakfast, including continental options, and free self-parking. > > > Beautiful farmhouse in Historic village, rated 9.2, offers a unique stay with mountain views and a kitchen. While its pet policy isn't explicitly detailed, its high rating and amenities suggest a welcoming environment for all guests. ### How much does a pet-friendly hotel in Chester cost? ### Are there any no fee pet-friendly hotels in Chester? > This motel, with a review rating of 8.4, stands out because pets stay free, making it a budget-friendly option for travellers with animals. It also offers complimentary breakfast, continental breakfast, self-parking, and free WiFi, adding to the value. ### Which area of Chester is best to stay in for pet-friendly hotels? > This central area of Chester is clustered around Main Street (Route 11) and North Street (Route 103), where you'll find most of the village's historic inns and guesthouses. It's a compact and walkable area with a town green, local shops, and eateries. The architecture is primarily historic New England, giving it a quaint feel. > > > Couples travelling with their furry companions will find this area particularly convenient. Many accommodations here understand the needs of pet owners, often providing amenities like dog beds or water bowls. You'll have easy access to village walks and nearby trails for exercising your pet, and several eateries have outdoor seating where pets are welcome. > > > For those looking for a slightly more secluded experience but still wanting pet-friendly options, areas just outside the immediate village centre, often along secondary roads, offer inns with more expansive grounds. ### What are some great pet-friendly hotels in Chester with outdoor spaces? > This highly-rated accommodation, with a 9.2 review score, stands out for its various outdoor spaces, including a patio, deck, and porch or lanai, providing ample room for pets to relax outdoors. It is also situated amidst the mountains, offering scenic views and nearby opportunities for mountain biking and climbing. ### How do I ensure I have booked a pet-friendly room in Chester? ### What pet-friendly activities should we do in Chester? > This area is the heart of Chester, offering a pleasant and accessible environment for you and your pet. Main Street is lined with historic buildings, local shops, and eateries, many of which welcome well-behaved pets. You'll find several spots with outdoor seating where you can dine with your dog by your side. > > > Couples travelling with their dogs will appreciate the convenience of staying in the village centre. It provides easy access to walkable streets and local parks, great for leisurely strolls. The Stone Village Historic District, just a short walk from Main Street, offers lovely architecture and quiet pathways for exploring with your canine companion. > > > For those who enjoy a bit of outdoor adventure with their pets, the trails accessible from the village centre are a great option. Many local walking paths and nearby state parks are dog-friendly, allowing you to enjoy Vermont's natural beauty together. ### What amenities should I look for in a pet-friendly hotel in Chester? ### How can I save on a pet-friendly hotel in Chester with Expedia? ### Do any Chester hotels have restrictions on pet sizes or breeds? ### Is it cheaper to book flights and a pet-friendly hotel in Chester as a package? ### Can I cancel my pet-friendly hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [B&B in Andover ](https://www.expedia.ca/Andover-Bed-And-Breakfast.d6023580-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Andover ](https://www.expedia.ca/Andover-Chalets.d6023580-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Andover ](https://www.expedia.ca/Andover-Country-House.d6023580-aaCountryHouse.Travel-Guide-Accommodation) - [Andover Hotels ](https://www.expedia.ca/Andover-Hotels.d6023580.Travel-Guide-Hotels) - 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