Title: Book the Best Chester Hotels with smoking rooms in 2025 from CA $101 | 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) ![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 Smoking Hotels in Chester, NY from CA $101 ![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 Hotels with smoking rooms Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Hotels with smoking rooms ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/9631af0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/da52c924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/903ceccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury Central Valley 9.2/10 Wonderful (1003) "Great place to stay, very clean and conveniently located" CA $165 CA $203 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/cefa7296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/747581be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/274a8ea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middletown - Goshen Middletown 8.4/10 Very good (1005) "great stay" CA $146 CA $173 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/dad3e76a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/77332016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/6eb104e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 2 Double Beds](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/366b5630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Point Motel Sussex 9.0/10 Wonderful (80) "Clean and quiet, beautiful views , adjacent to state park" CA $114 CA $128 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Sussex-Hotels-High-Point-Motel.h107253932.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) ![Breakfast area](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/6a619585.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) ![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) ### Appalachian Motel Vernon 7.6/10 Good (503) "I would stay here again" CA $88 CA $101 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Vernon-Hotels-Appalachian-Motel.h9665655.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38401260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/51570973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point New Windsor 8.4/10 Very good (1002) "Great price for a great hotel" CA $137 CA $155 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/78ebeb9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/c86c7344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/0dc23e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/c329caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Fishkill near Interstate 84 Fishkill 9.2/10 Wonderful (999) "The area around the hotel is fine with a diner within walking distance. Very convenient location to Beacon, and highway I-84. Hotel's conditions are excellent and clean." CA $166 CA $188 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Suites-Fishkill-Near-Interstate-84.h22934426.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/c9568c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/e40ff2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Quadruple Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/02c64296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave | Living area](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/6f763a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rolling Hills Motel Sussex 8.4/10 Very good (178) "Perfect spot to spend the nights of our wonderful getaway" CA $120 CA $134 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sussex-Hotels-Rolling-Hills-Motel.h57555387.Hotel-Information) ![Buffet](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/830db074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/7b83baec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/33748891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/eb75ea57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG Fishkill 8.4/10 Very good (1002) "Very good stay; as advertised." CA $195 CA $221 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/debdefae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/61ae6b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/e8396e3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/4ea3828f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn at Central Valley-Woodbury Central Valley 7.0/10 Good (1010) "Would stay here again very convenient " CA $138 CA $170 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Newburgh-Hotels-Americas-Best-Value-Inn-Central-Valley.h921510.Hotel-Information) ![Blackout drapes, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d07e2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/0e18f638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/945aae91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport New Windsor 9.2/10 Wonderful (1000) "We’ve stayed here once before and the service continues to be excellent. Breakfast buffet is great, staff is friendly and the rooms are clean and comfortable." CA $244 CA $277 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.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=2025-10-17&endDate=2025-10-18®ionId=6046665&adults=2&property_amenities_group_explore=designated_smoking_areas&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Good " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.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) - 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