Title: Book the Best Chester MOUNTAIN Hotels & Resorts in 2025 | 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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Mountain Hotels in Chester, VT from CA $109 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Mountain Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-24a9373a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2558x0y0-ab7af499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-b5950146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn and Suites Manchester Manchester Center 9.6/10 Exceptional (1003) "This was the best Hampton Inn I’ve stayed at, and location is excellent. " CA $189 CA $208 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/c828df52.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/ac65fd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel Springfield 8.8/10 Excellent (788) "Great and quiet place to stay overnight with kids. Big pool and good breakfast. " CA $225 CA $247 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.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) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/31952972.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) ### The Upper Pass Lodge at Magic Mountain Londonderry 8.2/10 Very good (667) "If this property was updated it would be a wonderful place to stay but as is it’s like a very old motel. I would not stay there again. " CA $99 CA $109 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/0f0b56c0.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) ![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) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (96) "Sweet place to stay" CA $389 CA $425 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/05237c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/302c3d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/a73c2787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Shire Woodstock Woodstock 8.8/10 Excellent (841) "great location and the staff were great" CA $184 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/c701f02d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/9a97fc0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/6852cc27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/91b36201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Olympia Lodge Manchester Center 9.4/10 Exceptional (543) "Perfect spot for Green Mountain Festival" CA $250 CA $275 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Bennington-Hotels-The-Olympia-Lodge.h9257616.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/39000000/38990000/38987300/38987280/afb0605c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, Multiple Beds, Non Smoking, Mountain View](https://images.trvl-media.com/lodging/39000000/38990000/38987300/38987280/9c2d18f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/39000000/38990000/38987300/38987280/eb2cef8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/39000000/38990000/38987300/38987280/979921b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stanford House Manchester Center 9.0/10 Wonderful (61) "good basic bed for traveling " CA $175 CA $210 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Bennington-Hotels-The-Stamford-Motel.h38987280.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) ![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) ![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) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG Brownsville 9.0/10 Wonderful (757) "It is Good place to stay. We enjoyed our stay here." CA $236 CA $276 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/d22bae40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/99da9548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/6142d87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/c7e6e735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Winds Country Motel Manchester Center 8.4/10 Very good (513) "The check in was very quick and staff was friendly. The room is clean, comfortable, and quiet. " CA $137 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Four-Winds-Country-Motel.h7640832.Hotel-Information) ![Mountain view](https://images.trvl-media.com/lodging/9000000/8340000/8330600/8330598/474a4f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/9000000/8340000/8330600/8330598/3bad0719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8340000/8330600/8330598/3490b342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/9000000/8340000/8330600/8330598/9e031538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aerie Inn of Vermont East Dorset 9.4/10 Exceptional (171) "So quaint and staff was super friendly and accommodating! We are looking forward to coming back again! " CA $184 CA $201 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-Aerie-Inn-Of-Vermont.h8330598.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=2025-10-19&endDate=2025-10-20®ionId=89014&adults=2&location_highlights_explore=mountain&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "The grounds around the hotel are beautiful. The rooms are very nice and comfortable. Paige the bartender is awesome. Breakfast was very good, highly recommend the skillet breakfast." [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Wonderful accommodation " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Very clean, up to date, affordable" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![The Shire Woodstock](//images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river. " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "It was quiet and the staff was friendly. Great and easy to get to location." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "The property was beautiful and well-maintained, and the staff were helpful and friendly. I had a great stay and will definitely be returning in the future. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![Days Inn by Wyndham Keene NH](//images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg) ### Days Inn by Wyndham Keene NH 10/10 Excellent "A group of us come here every year and we never hesitate to come back. Not the Ritz, but perfectly fine and very reasonably priced to have access to a pretty nice part of NH." [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Good location and value" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [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) - 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[Resorts in Grafton](https://www.expedia.ca/Grafton-Resort-Hotels.d184049-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Magic Mountain Ski Resort](https://www.expedia.ca/Magic-Mountain-Ski-Resort-Hotels.0-l6115886-0.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in North Springfield](https://www.expedia.ca/North-Springfield-Hotels-Pet-Friendly-Hotel.0-0-d184061-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in North Springfield](https://www.expedia.ca/North-Springfield-Hotels-Spa-Hotel.0-0-d184061-tSpaHotel.Travel-Guide-Filter-Hotels) - [North Springfield Hotels](https://www.expedia.ca/North-Springfield-Hotels.d184061.Travel-Guide-Hotels) - [Resorts in North Springfield](https://www.expedia.ca/North-Springfield-Resort-Hotels.d184061-aaResortHotels.Travel-Guide-Accommodation) - [Castles in Proctorsville](https://www.expedia.ca/Proctorsville-Castles.d6023678-aaCastles.Travel-Guide-Accommodation) - [Honeymoon Resorts and in Proctorsville](https://www.expedia.ca/Proctorsville-Hotels-Honeymoon-Hotels.0-0-d6023678-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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[Springfield Hotels](https://www.expedia.ca/Springfield-Hotels.d10292.Travel-Guide-Hotels) - [Resorts in Springfield](https://www.expedia.ca/Springfield-Resort-Hotels.d10292-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Hotels.0-l553248621532666908-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Weston](https://www.expedia.ca/Weston-Hotels-Business-Hotel.0-0-d177460-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Weston](https://www.expedia.ca/Weston-Hotels-Luxury-Hotel.0-0-d177460-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Windham](https://www.expedia.ca/Windham-Bed-And-Breakfast.d6150553-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Windham](https://www.expedia.ca/Windham-Hotels-Couples-Resorts-Hotels.0-0-d6150553-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Windham Hotels](https://www.expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels) - [Resorts in Windham](https://www.expedia.ca/Windham-Resort-Hotels.d6150553-aaResortHotels.Travel-Guide-Accommodation) - [Flights from Springfield](https://www.expedia.ca/lp/flights/10292/flights-from-springfield) - [Flights from Grafton](https://www.expedia.ca/lp/flights/184049/flights-from-grafton) - [Flights from Columbia (CAE) to Springfield (VSF)](https://www.expedia.ca/lp/flights/cae/vsf/columbia-to-springfield) - [Flights from Charlotte (CLT) to Springfield (VSF)](https://www.expedia.ca/lp/flights/clt/vsf/charlotte-to-springfield) - [Flights from Wilmington (ILM) to Springfield (VSF)](https://www.expedia.ca/lp/flights/ilm/vsf/wilmington-to-springfield) - [Flights from Minneapolis (MSP) to Springfield (VSF)](https://www.expedia.ca/lp/flights/msp/vsf/minneapolis-to-springfield) - [Flights from Ottawa (YOW) to Springfield (VSF)](https://www.expedia.ca/lp/flights/yow/vsf/ottawa-to-springfield) - [Andover Vacations](https://www.expedia.ca/Andover.d6023580.Destination-Travel-Guides) - [Visit Andover](https://www.expedia.ca/Andover.dx6023580) - [Fletcher Farm School for the Arts and Crafts](https://www.expedia.ca/Fletcher-Farm-School-For-The-Arts-And-Crafts-Ludlow.d553248621532666921.Vacation-Attraction) - [Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction) - [Visit Weston](https://www.expedia.ca/Weston.dx177460) - [Car rental Grafton](https://www.expedia.ca/Car-Rentals-In-Grafton.d184049.Car-Rental-Guide) - [Car rental Windham](https://www.expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide)