Title: Book the Best Chester Ski Hotels in 2026 from CA $94 | 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)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[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 [Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-11&endDate=2026-03-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-12&endDate=2026-03-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-20&endDate=2026-03-22&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) ![Dining](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/0b7fdcd8.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/78c81c21.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 8.2/10 Very good (422 reviews) CA $175 CA $191 total includes taxes & fees Mar 12 - Mar 13 [](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) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.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) ### Stone Hearth Inn and Eatery [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (115 reviews) - Embrace winter adventure at this mountain-side bed & breakfast where cozy rooms await after a day of cross-country skiing and snowshoeing. CA $284 CA $309 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.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, 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) ![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) ![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 (840 reviews) CA $184 CA $202 total includes taxes & fees Mar 12 - Mar 13 [](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) ![Standard Double Room, 2 Double Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/a5ea8fc8.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) ### The Covered Bridge Inn [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) Brattleboro 7.6/10 Good (1,008 reviews) - Carve fresh powder minutes from this cozy Brattleboro retreat, with complimentary breakfast and easy access to multiple Vermont ski areas. CA $85 CA $94 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/81424597.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 (950 reviews) - Embrace the slopes of Vermont with access to nearby ski mountains and a revitalizing hot tub after your winter adventures. CA $144 CA $158 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) Keene 8.4/10 Very good (1,000 reviews) CA $162 CA $176 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/54d53274.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 (782 reviews) - Ski lodge warmth meets modern comforts at this Brattleboro retreat, where powder adventures begin steps from your cozy mountain base. CA $153 CA $168 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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/a0514206_edited_9a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/bbf5ae58.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 (70 reviews) CA $184 CA $202 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/3536a275.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) ![Electric vehicle charging station](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/083f3b70.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 (559 reviews) CA $105 CA $163 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Room 4](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/22815dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/81dd974d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/7fbb1dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) Brattleboro 9.8/10 Exceptional (349 reviews) - Immerse in winter magic at this historic Brattleboro bed & breakfast, offering doorstep access to six thrilling snow adventures. CA $214 CA $235 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.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=2026-03-25&endDate=2026-03-26®ionId=89014&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at ski hotels in Chester Resort 4 stars 5 stars Spa Family-friendly ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_89014) ## Top Chester Hotel Reviews ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg) ### Pointe at Castle Hill Resort 8/10 Good "Yes" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "It was good to have pool option after a ski day" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae_y.jpg) ### Best Western Springfield Hotel 10/10 Excellent " Nice clean room. Good breakfast. Friendly staff check in with help finding dining spots in area. " [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Fullerton Inn](https://images.trvl-media.com/lodging/16000000/15850000/15845400/15845368/662925ab_y.jpg) ### Fullerton Inn 8/10 Good "Gorgeous old Inn that is fairly well maintained to keep up with modern competition. We visited in the dead of winter so the quaint town of Chester, VT didn’t have a lot to offer. We plan on visiting again in the summer to get the full experience!" [](https://expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 4/10 Poor "Front entrance floor was dirty; bedside table had trash in it. TV kept going out (excessively); no shower curtain (but quickly replaced by staff), no bathmat. And, shower screeched the entire time it was on. " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "Great location, most convenient hotel , everything is perfect. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Nine " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Grand Summit Resort, A Vail Resorts Property](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/7d1f7aea_y.jpg) ### Grand Summit Resort, A Vail Resorts Property 8/10 Good "Staff were all friendly. Room was clean. Food at the resort restaurant was great. We have been stay at this hotel many times in the past but were delighted seeing there are on site EV charging stations now. It is a nice add-on. However, one may be lucky or unlucky to get a charging space when stay in the hotel, depends on if people are courtesy enough to move their car away quickly when their finished charging. We didn't have the luck this time at our stay. " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187_y.jpg) ### The Equinox Golf Resort & Spa 4/10 Poor "The staff were lovely but the property is definitely showing signs of age and neglect. The property needs to be cleaned up and maintained a bit better. Hot tub wasn't working when we were there. " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ## 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) - [Inns in Andover ](https://www.expedia.ca/Andover-Inns.d6023580-aaInns.Travel-Guide-Accommodation) - [Motels in Andover ](https://www.expedia.ca/Andover-Motels.d6023580-aaMotels.Travel-Guide-Accommodation) - [Resorts in Andover ](https://www.expedia.ca/Andover-Resort-Hotels.d6023580-aaResortHotels.Travel-Guide-Accommodation) - [Hotels with a Pool in Athens ](https://www.expedia.ca/Athens-Hotels-Hotel-With-Pool.0-0-d553248634998621896-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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