Title: Book the Best Chester MOUNTAIN Hotels & Resorts in 2026 | 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) # Find Mountain Hotels in Chester, VT from CA $153 - ![](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 Mountain Hotels Tonight [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels with mountains nearby ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5.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) ![Deluxe Room, 1 Queen Bed, Garden View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/20cd6ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/327ad7fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (107) "Good breakfast and dinner options. Great location for hiking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $269 CA $294 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/a1626ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/w1536h1021x0y3-8fc8ac6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/3794da32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/1377c15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room in Historic Inn! 20 Minutes to Okemo! Chester Depot 9.2/10 Wonderful (18) "The Chester Inn was beautiful and located in downtown Chester. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter C. CA $166 CA $267 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/8f3740a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/a0f7ed6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/dd8ab6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/98b36931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont Cabin · Mountain Views · Near Okemo Chester 10/10 Exceptional (3) "We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald M. CA $747 CA $1,381 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/7656b8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/6d1c5ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/a93524b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/d309381b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King & Queen Suite in Historic Inn Circa 1780 Chester Depot 9.8/10 Exceptional (16) "Central for our needs. easy check in process. Lovely large room with comfy beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HIlary H. CA $359 CA $527 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Chester-Hotels-King-Queen-Suite-In-Historic-Inn-Circa-1780.h83938140.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) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/44151c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bromley View Inn Bondville 9.0/10 Wonderful (402) "Overall a decent stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Libin [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![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/ac65fd90.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel Springfield 8.8/10 Excellent (803) "so clean and friendly it was a perfect stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colette CA $198 CA $218 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/286eff53.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/c8df49db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Studio Suite](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/79903cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/d5eb5082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Mt. Snow West Dover 10/10 Exceptional (2) "Tout y était!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Martin CA $200 CA $221 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Garden View | Living area](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/074a9a47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/1525a0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/ad9a6e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Weathersfield Perkinsville 9.8/10 Exceptional (70) "The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/61c9c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/501f4323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/978b1784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG Brownsville 9.0/10 Wonderful (777) "Very welcoming, spacious, clean. Perfect for a family of 4\. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $165 CA $202 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Exclusive Suite, Multiple Beds, Kitchenette, Mountain View](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room, 1 Double Bed](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/99257ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/80ab5ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/31952972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Upper Pass Lodge at Magic Mountain Londonderry 8.2/10 Very good (686) "Wery good diner" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yelena CA $138 CA $153 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.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=2025-12-23&endDate=2025-12-24®ionId=89014&adults=2&location_highlights_explore=mountain&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Room was clean and smelled good, no unpleasant odors. Check-in very polite and helpful." [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/9c9da73f_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! " [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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 "Great place to stay while skiing at okemo" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "The staff are amazing! So friendly and welcoming. The lodge is so cute! The rooms were spotless and the hottub sparkling clean. The shuttle service until 10 pm was fantastic and the shuttle driver was very nice. We can't wait to visit again! " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Wonderful place to stay!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Jackson Gore Village](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "Great location, pool, hot tub, game room, staff." [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.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) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n go off for the day. All was very nice. Thank you!" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![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 "Very welcoming, spacious, clean. Perfect for a family of 4\. 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