Title: Book the Best Chester Ski Hotels in 2026 from CA $112 | 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 Ski Hotels Tonight [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-19&endDate=2026-01-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 20 - Jan 21](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-20&endDate=2026-01-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester ski hotels ![Garden](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/9dfa0135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/c887af2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fullerton Inn [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) Chester Depot 8.0/10 Very good (409 reviews) "The room smelled really good but the beds were hard." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha CA $179 CA $196 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/ae105a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Mountain View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/48815e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (109 reviews) "So great all around!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $388 CA $423 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![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) ![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) ![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) ### 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 $407 CA $788 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chester-Hotels-Spacious-Chalet-For-Picturesque-Fall-Getaway-Winter-Fun-At-Okemo.h68850104.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) ![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) ![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) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 8.8/10 Excellent (27 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) ![Porch](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/f967c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/8607e1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/6a517157.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Manchester View [](https://www.expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) Manchester Center 9.4/10 Exceptional (799 reviews) "Great staff, huge clean room, tasty continental breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carey CA $146 CA $161 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/46351656.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) ### 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 $212 CA $233 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/c5f36674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/41382b96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) Brattleboro 7.6/10 Good (1,001 reviews) "Easy check in and good parking" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) nicholas CA $102 CA $112 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/322811f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/776c9b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/51ea72b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) Brattleboro 8.6/10 Excellent (758 reviews) "The room was clean and the staff was wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianne CA $186 CA $205 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/5c506444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/819de6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Keene Downtown [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) Keene 8.8/10 Excellent (759 reviews) "Everything was clean, comfortable and the staff quite conversational" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $244 CA $264 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/f5b14dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/989e1da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) Brattleboro 8.2/10 Very good (936 reviews) "Good breakfast, great staff and very good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valdeci CA $204 CA $225 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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=2026-02-02&endDate=2026-02-03®ionId=89014&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Fantastic! Easy check in and out! Rooms were updated and spotless. Great customer service!" [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Everything/everyone was superb!!! " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![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) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Our stay was absolutely wonderful. The room was clean & comfortable with a nice view from balcony. The breakfast was good & the bar was very nice on a cold evening. Look forward to staying here again." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Ski on skis off fantastic. Ski valet right on it " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg) ### Bromley View Inn 10/10 Excellent "Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!" [](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Every thing was excellent " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg) ### Aspen At Manchester 10/10 Excellent "Everything was good, The refrigerator was barely working, so we had to take the food outside." 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