Title: Book the Best Chester Ski Hotels in 2026 from CA $99 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Black dirt region farm Chester New York](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in Chester, NY from CA $99 - ![](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 [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester ski hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/93b27f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/7c606992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/cf710d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Middletown [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) Middletown 8.6/10 Excellent (1003) "Room was clean and staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annemarie CA $112 CA $133 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/a8ff6ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/3765bbd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/2c0824e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/24286d85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn near Mountain Creek [](https://www.expedia.ca/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) Vernon 7.6/10 Good (973) "Nice hotel. Close to golf," ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $118 CA $135 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/61f4bfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/b675c11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/ae4d02f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Suffern - Mahwah by IHG [](https://www.expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) Suffern 8.8/10 Excellent (1007) "Good location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glenn CA $152 CA $176 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/bf708146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/4334c96b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/339067b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Ramsey-Mahwah by IHG [](https://www.expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) Ramsey 9.2/10 Wonderful (1001) "Clean room, very nice staff, bountiful breakfast. Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna Marie CA $151 CA $174 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/275854de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/e34f60f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/11f1915d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Newburgh Stewart Airport [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) Newburgh 9.2/10 Wonderful (977) "Clean great staff great breakfast pool area warm " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LaRhonda CA $142 CA $168 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Free self parking](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/45d9ec54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/dcfab2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/11731bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/420a5df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appalachian Motel [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Motel.h9665655.Hotel-Information) Vernon 7.6/10 Good (515) "I would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyanlex CA $87 CA $99 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Motel.h9665655.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hanlon Suite | Children's theme room](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/05c3d7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/25051ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/91f0a8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (144) "Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/d1eaddcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/4f4f5ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/57a57bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/32997d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Mahwah [](https://www.expedia.ca/Mahwah-Hotels-Super-8-By-Wyndham-Mahwah.h1157.Hotel-Information) Mahwah 7.4/10 Good (1001) "Room was clean and staff was helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Berldwin CA $104 CA $119 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Mahwah-Hotels-Super-8-By-Wyndham-Mahwah.h1157.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free rollaway beds](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/15889b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/6383ea7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/67a03857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Mahwah [](https://www.expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) Mahwah 8.8/10 Excellent (1419) "Amazing hotel, felt safe for my family and I. Will recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brittney CA $142 CA $163 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/d11440c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/667bc407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/f101dd2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/c09894ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western The Inn At Ramsey [](https://www.expedia.ca/Ramsey-Hotels-Best-Western-The-Inn-At-Ramsey.h473490.Hotel-Information) Ramsey 7.2/10 Good (1004) "Room clean, staff helpful & courteous." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $117 CA $134 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ramsey-Hotels-Best-Western-The-Inn-At-Ramsey.h473490.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=2025-12-27&endDate=2025-12-28®ionId=6046665&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Room is perfect for what it is. Clean, quiet very comfortable. " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "Check in was easy, room was nice and clean, breakfast was nice and convenient in the morning. No issues at all." [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Clean nice" [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Courtyard by Marriott Montvale](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/5623b54c_y.jpg) ### Courtyard by Marriott Montvale 10/10 Excellent "Clean, comfortable space. Friendly staff. " [](https://expedia.ca/Montvale-Hotels-Courtyard-By-Marriott-Montvale.h21786.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "Clean room, great breakfast " [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Great to stay!! Some furniture needs updating." [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "He was excellent our two nights and thank again, see you soon." [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Clean room and easy check in. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Homewood Suites by Hilton Mahwah](https://images.trvl-media.com/lodging/1000000/700000/699300/699247/85ff4dc1_y.jpg) ### Homewood Suites by Hilton Mahwah 10/10 Excellent "Very nice location super clean with a friendly staff" [](https://expedia.ca/Mahwah-Hotels-Homewood-Suites-By-Hilton-Mahwah.h699247.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Hotels-With-Free-Breakfast.0-0-d3000448042-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall ](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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