Title: Book The Best Hotels in Chester, NY for 2026 from CA $107 - Competitive Prices - Expedia.ca [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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 ## Go beyond your typical stay in Chester Pool [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&amenities=POOL) Spa [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&amenities=SPA_ON_SITE) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&amenities=HOT_TUB) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&travelerType=family_friendly) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=CABIN) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&amenities=PETS) Farm [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=AGRITOURISM) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&amenities=WATER_PARK) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=COTTAGE) Condo [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=CONDO) Villa [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-02-25&d1=2026-02-25&endDate=2026-02-27&d2=2026-02-27&lodging=VILLA) ## Check prices for these dates Tonight [Feb 11 - Feb 12](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-11&endDate=2026-02-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 12 - Feb 13](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-12&endDate=2026-02-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/308be1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/309e00bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Chester 8.6/10 Excellent (1,000 reviews) "great stay. had everything needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana CA $137 CA $162 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/117bcdbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/f9a6b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/98e48046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/3cff05ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast [](https://www.expedia.ca/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) Chester 9.2/10 Wonderful (233 reviews) "Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erek CA $291 CA $330 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/605b2de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/4856168e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/abf8ab38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (823 reviews) "The staff was great! The room was clean and the breakfast was excellent." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Joey CA $119 CA $135 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Indoor pool, open 8:30 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/800/736/df09fa9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/800/736/b3a2ed01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Nanuet [](https://www.expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) Nanuet 9.0/10 Wonderful (1,069 reviews) "Clean room, helpful staff and good bar/restaurant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $138 CA $160 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/f8e0b8a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/93d1f26a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/213a567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Simply Suites Nanuet [](https://www.expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) Nanuet 8.4/10 Very good (1,077 reviews) "Staff was nice, bed comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Misty CA $121 CA $141 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/f02832d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/354c26b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/a3d8c842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Nanuet [](https://www.expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) Nanuet 7.8/10 Good (1,000 reviews) "Great hotel, nice and clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $110 CA $128 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/49000000/48940000/48934500/48934496/8b82c4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/49000000/48940000/48934500/48934496/e88012ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48940000/48934500/48934496/b9193c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/49000000/48940000/48934500/48934496/4bc7e0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvest Inn [](https://www.expedia.ca/Newburgh-Hotels-Harvest-Inn.h48934496.Hotel-Information) Pine Bush 9.4/10 Exceptional (560 reviews) "Staff was friendly and accommodating. The place was very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shirley [](https://www.expedia.ca/Newburgh-Hotels-Harvest-Inn.h48934496.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/dad3e76a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 1 Queen Bed](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/8995b312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/9bba8a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Point Motel [](https://www.expedia.ca/Sussex-Hotels-High-Point-Motel.h107253932.Hotel-Information) Sussex 9.2/10 Wonderful (112 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob CA $103 CA $116 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Sussex-Hotels-High-Point-Motel.h107253932.Hotel-Information) ![Individually decorated, individually furnished, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/2952b2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/1903c9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/421c5d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172100/172075/2336337b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Nanuet / Spring Valley [](https://www.expedia.ca/Nyack-Hotels-Days-Inn-By-Wyndham-Nanuet-Spring-Valley.h172075.Hotel-Information) Nanuet 7.0/10 Good (1,001 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deon Francine CA $137 CA $160 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Nyack-Hotels-Days-Inn-By-Wyndham-Nanuet-Spring-Valley.h172075.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) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/00e54810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/2154c327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.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 (150 reviews) "Breakfast was hot and tasty. Staff were all pleasant and accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) wendy [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5265cb34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/8f959dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/669fa011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Nanuet [](https://www.expedia.ca/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) Nanuet 7.8/10 Good (1,001 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) enmanuel CA $132 CA $154 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/94000000/93140000/93135700/93135696/cb4d648c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/94000000/93140000/93135700/93135696/11e85be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/94000000/93140000/93135700/93135696/8d257ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/94000000/93140000/93135700/93135696/e7e6cbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hamlet Inn at Warwick [](https://www.expedia.ca/Warwick-Hotels-The-Hamlet-Inn-At-Warwick.h93135696.Hotel-Information) Warwick 7.6/10 Good (154 reviews) "good accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro CA $129 CA $146 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Warwick-Hotels-The-Hamlet-Inn-At-Warwick.h93135696.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very good (1,000 reviews) "The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith CA $134 CA $152 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58071d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/w5520h3677x0y0-69f9a2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/ab21b3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) Peekskill 9.2/10 Wonderful (1,006 reviews) "Very comfortable beds,clean and breakfast was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $165 CA $189 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/d4243906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/6eaf4dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/f3942ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Full Accessible](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/42025e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Abbey Inn & Spa [](https://www.expedia.ca/White-Plains-Hotels-The-Abbey-Inn-Spa.h45603202.Hotel-Information) Peekskill 9.2/10 Wonderful (239 reviews) "Friendly staff and a great place to get away and recharge!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ariana CA $440 CA $566 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/White-Plains-Hotels-The-Abbey-Inn-Spa.h45603202.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/ae4d02f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/f6dc454b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/0564b8da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/163b5068.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 (1,001 reviews) "Great place to stay. Great Custumer service and very comfortable rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samir CA $152 CA $177 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Comfort Room, 2 Double Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/71000000/70390000/70385000/70384905/42635aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 1 Double Bed, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/71000000/70390000/70385000/70384905/1d0da796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70390000/70385000/70384905/5b33ee80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/71000000/70390000/70385000/70384905/4de173b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sussex Motel [](https://www.expedia.ca/Sussex-Hotels-Sussex-Motel.h70384905.Hotel-Information) Sussex 8.8/10 Excellent (382 reviews) "Yes really good people and great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan CA $103 CA $115 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Sussex-Hotels-Sussex-Motel.h70384905.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/7d4cc9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/d05dbb0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/941ff0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/7091d89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cold Spring Hotel [](https://www.expedia.ca/Poughkeepsie-Hotels-Cold-Spring-Hotel.h23005170.Hotel-Information) Cold Spring 8.6/10 Excellent (155 reviews) "The owner is so warm and kind. The room was clean. Great place to stay for the weekend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wydayessi CA $317 CA $364 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Poughkeepsie-Hotels-Cold-Spring-Hotel.h23005170.Hotel-Information) ![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 | Bathroom](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/fef47c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/c9568c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/58000000/57560000/57555400/57555387/57b8670c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rolling Hills Motel [](https://www.expedia.ca/Sussex-Hotels-Rolling-Hills-Motel.h57555387.Hotel-Information) Sussex 8.6/10 Excellent (200 reviews) "Room was very spacious, easy check in and check out procedure, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KIRK CA $107 CA $120 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Sussex-Hotels-Rolling-Hills-Motel.h57555387.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3590000/3585600/3585599/14e211ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3590000/3585600/3585599/a9736e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/4000000/3590000/3585600/3585599/cbc0210a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/4000000/3590000/3585600/3585599/c68687b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Budget Motor Inn - Stony Point [](https://www.expedia.ca/Nyack-Hotels-Budget-Motor-Inn-Stony-Point.h3585599.Hotel-Information) Stony Point 5.0/10 (507 reviews) "The staff were extremely friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $80 CA $89 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Nyack-Hotels-Budget-Motor-Inn-Stony-Point.h3585599.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=2026-02-25&endDate=2026-02-26®ionId=6046665&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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=HTG_SPRING_PROMO_6046665) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6046665.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6046665.Travel-Guide-Hotels) ## Stay near popular Chester attractions ### The Rock Sports Complex 4.0/5 (10 reviews) Explore the great outdoors at The Rock Sports Complex, a lovely green space in Chester. While you're in the area, find time to visit its shops. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248624556330411) ### Museum Village 4.5/5 (4 reviews) You can spend an afternoon exploring the galleries in Museum Village during your trip to Chester. While in this family-friendly area, find time to visit its shops. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621559142200) ### Goosepond Mountain State Park 4.0/5 (3 reviews) You can take time to visit Goosepond Mountain State Park during your travels to Chester. Visit the shops in this family-friendly area, or simply enjoy its restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635974861777) ## Learn more about Chester Lace up your hiking boots and hit the trails at Goosepond Mountain State Park for stunning views. After working up an appetite, head to Castle Fun Centre for go-karts, mini-golf, and arcade games. [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-25&endDate=2026-02-26&adults=2®ionId=6046665) ![Black dirt region farm Chester New York](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=900&h=550&p=1&q=high) ## Top Chester Hotel Reviews ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "Very nice staff its clean and warm. They also have a very good outdoor team to clean up the snow. " [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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 "Good" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Everyone was very helpful." [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg) ### Sleep Inn & Suites Monroe - Woodbury 10/10 Excellent "The assistant manager was amazing. She was so easy to talk to and really accommodated me and my family." [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![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 "Everything was perfect" [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Everything was great. Staff was great" [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.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 "Great place to stay. Great Custumer service and very comfortable rooms." [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.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 "stayed close to my job when there was a snowstorm. everything good." [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Thank you to the staff at DoubleTree in Nanuet, NY. Excellent service Clean rooms Respectful staff Great breakfast. Thank you again… 😊" [](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ## More cheap stays in Chester ![Super 8 by Wyndham Mahwah](https://images.trvl-media.com/lodging/1000000/10000/1200/1157/d1eaddcb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Super 8 by Wyndham Mahwah 160 State Route 17 South Mahwah NJ CA $106 CA $122 total Feb 15 - Feb 16 includes taxes & fees 7.4/10 Good! (1,000 reviews) [](https://expedia.ca/Mahwah-Hotels-Super-8-By-Wyndham-Mahwah.h1157.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Nanuet 20 Overlook Blvd Nanuet NY CA $121 CA $141 total Feb 12 - Feb 13 includes taxes & fees 8.4/10 Very Good! (1,077 reviews) [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sleep Inn & Suites Middletown - Goshen 3491 Route 6 Middletown NY CA $126 CA $148 total Mar 4 - Mar 5 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Mahwah 290 Rt 17s Mahwah NJ CA $130 CA $150 total Feb 25 - Feb 26 includes taxes & fees 8.8/10 Excellent! (1,461 reviews) [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express Ramsey-Mahwah by IHG 946 Route 17 North Ramsey NJ CA $144 CA $165 total Feb 22 - Feb 23 includes taxes & fees 9.2/10 Wonderful! (1,003 reviews) [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Harriman Woodbury 60 Centre Dr Central Valley NY CA $143 CA $177 total Feb 19 - Feb 20 includes taxes & fees 9.2/10 Wonderful! (1,055 reviews) [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ## Hotels in Chester with star rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 7 properties [](https://expedia.ca/4Star-Chester-Hotels.s40-0-d6046665.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 123 properties [](https://expedia.ca/3Star-Chester-Hotels.s30-0-d6046665.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 145 properties [](https://expedia.ca/2Star-Chester-Hotels.s20-0-d6046665.Travel-Guide-Filter-Hotels) ## Find out more about Chester ### Top reasons to visit Chester - **Natural Beauty:** Chester boasts stunning landscapes, including national parks and scenic lakes, perfect for outdoor enthusiasts. - **Family-Friendly Activities:** The area offers a variety of engaging activities suitable for all ages, ensuring a fun-filled vacation. - **Chester Park:** Unwind at Chester Park, a lovely spot to relax and soak in the picturesque surroundings. - **Diverse Accommodations:** Enjoy a range of lodging options, from charming hotels to unique agritourism stays that cater to every traveller's needs. - **Vibrant Neighbourhoods:** Explore friendly local communities and bustling malls, offering a taste of Chester's lively atmosphere. ### Find great hotels near Chester Chester, New York, offers a variety of lodging options to suit every traveller's needs, from charming hotels to unique agritourism properties. Whether you're seeking a pet-friendly family retreat or a business-oriented stay, you'll discover top-notch accommodations that blend comfort with convenience. Explore the best hotels in the area, perfect for creating memorable experiences while enjoying the beauty of Chester and its surroundings. - **[Super 8 by Wyndham Middletown: ](https://www.expedia.ca/Newburgh-Hotels-Super-8-By-Wyndham-Middletown.h459783.Hotel-Information)** Experience comfort and convenience at Super 8 by Wyndham Middletown, a welcoming motel situated 14.5km from Chester. With a focus on affordability and practicality, this property features a variety of dining options, including WrappedFood and WrappedFood:Breakfast to help kickstart your day. Guests can unwind with entertainment options such as television, satellite TV, and premium channels. Additionally, nearby outlet shopping offers great retail therapy, making it a perfect choice for families or solo travellers seeking an uncomplicated stay. - **[Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: ](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information)** This family-friendly hotel, located 22.5km from Chester, is ideal for those seeking a pet-friendly and inclusive atmosphere. Red Roof Inn & Suites Newburgh embraces diversity, catering to LGBTQIA travellers and families alike with amenities designed for children, including free cribs. Its pet policy allows for dogs and cats, ensuring your furry companions are welcome too. The inviting environment fosters a sense of community, making it a great base for exploring the nearby attractions. - **[Howard Johnson by Wyndham Newburgh/West Point: ](https://www.expedia.ca/Newburgh-Hotels-Howard-Johnson-By-Wyndham-NewburghWest-Point.h7652.Hotel-Information)** Tailored for business travellers, Howard Johnson by Wyndham Newburgh/West Point is located 22.5km from Chester and offers a professional yet comfortable atmosphere. With facilities designed to support your business needs, including meeting spaces and high-speed internet access, this hotel ensures you stay productive during your visit. Its strategic location allows easy access to local businesses and attractions, making it a smart choice for those balancing work and leisure. ### Where to stay near Chester Chester, New York, offers an idyllic escape for families and city enthusiasts alike. Explore vibrant neighbourhoods with friendly locals, indulge in bustling malls, and take in the stunning New York scenery. Whether you're seeking a weekend getaway or a lively city experience, Chester provides a delightful mix of budget and luxury options, ensuring a memorable vacation for everyone. - **[Middletown: ](https://www.expedia.ca/Middletown-Hotels.d8864.Travel-Guide-Hotels)** Located approximately 16.1km from Chester, Middletown offers a vibrant city experience perfect for families and entertainment seekers alike. With a mix of year-round attractions, visitors often flock to the local shopping centres and malls, making it a great hub for retail therapy. Highlights include a nearby theme park and picturesque lakes that provide scenic views and recreational activities. The city is particularly lively in April and from June to July, ensuring a dynamic atmosphere for tourists. - **[Goshen: ](https://www.expedia.ca/Goshen-Hotels.d8005.Travel-Guide-Hotels)** Just 6.4km from Chester, the city of Goshen is a delightful destination renowned for its family-friendly and entertainment-oriented experiences. The charming modern square and various resorts are popular among visitors, offering a blend of relaxation and excitement. Goshen hosts a steady stream of tourists, especially during peak months in March, July, and September. Notable attractions include a local theme park and a bustling tourist precinct, making it a must-visit for those looking to explore. - **[Monroe: ](https://www.expedia.ca/Monroe-Hotels.d6171715.Travel-Guide-Hotels)** Located 8.0km from Chester, Monroe is a city that offers a unique blend of family, business, and city-themed experiences. Visitors are drawn to its shopping mall centres and resorts, ensuring a comfortable stay with plenty to do. The city peaks in visitor numbers during the summer months of June to July and again in September. Monroe is home to stunning local landmarks, including a nearby theme park, beautiful lakes, and scenic mountains, ideal for outdoor enthusiasts and families seeking adventure. ### Things to do in and around Chester Chester, New York, is an ideal destination for families and those seeking entertainment or city adventures. Visitors can enjoy a variety of activities, including resort stays, shopping at local malls, and exploring the area's best attractions. Whether you're interested in city sightseeing, exciting day trips, or outdoor experiences, Chester offers a range of options to create lasting memories during your vacation. **Shopping** In Chester, you can shop at [Monroe Federal Plaza Shopping Center](https://www.expedia.ca/Monroe-Federal-Plaza-Shopping-Center-Hotels.0-l553248621558038864-0.Travel-Guide-Filter-Hotels), 9.7km away, offering a lively atmosphere. [Soons Orchards](https://www.expedia.ca/Soons-Orchards-Hotels.0-l6229734-0.Travel-Guide-Filter-Hotels), 11.3km away, provides a great selection of local produce. If you're up for a drive, explore [Old Glory Mall Shopping Center](https://www.expedia.ca/Old-Glory-Mall-Shopping-Center-Hotels.0-l553248621558038867-0.Travel-Guide-Filter-Hotels), located 12.9km from Chester, for a variety of family-friendly shops. **Recreation** At [The Rock Sports Complex](https://www.expedia.ca/The-Rock-Sports-Complex-Hotels.0-l553248624556330411-0.Travel-Guide-Filter-Hotels), enjoy a vibrant atmosphere filled with various sports activities. For a touch of luxury, visit [The Golf Club at Mansion Ridge](https://www.expedia.ca/The-Golf-Club-At-Mansion-Ridge-Hotels.0-l553248621532664441-0.Travel-Guide-Filter-Hotels) for a round of golf amidst stunning scenery. Lastly, unwind at [Thomas Bull Memorial Park](https://www.expedia.ca/Thomas-Bull-Memorial-Park-Hotels.0-l553248621555565638-0.Travel-Guide-Filter-Hotels), where you can relax and rejuvenate in nature. **Adventure** Experience the thrill of motor racing at [Orange County Fair Speedway](https://www.expedia.ca/Orange-County-Fair-Speedway-Hotels.0-l6182288-0.Travel-Guide-Filter-Hotels), located 14.5km from Chester. For winter sports enthusiasts, [Mount Peter Ski Area](https://www.expedia.ca/Mount-Peter-Ski-Area-Hotels.0-l553248621532664438-0.Travel-Guide-Filter-Hotels), 12.9km away, offers fantastic skiing opportunities. Alternatively, explore the [Continental Road Trailhead](https://www.expedia.ca/Continental-Road-Trailhead-Hotels.0-l553248635974865870-0.Travel-Guide-Filter-Hotels), a scenic outdoor trail also 12.9km from Chester, perfect for hiking adventures. **Nightlife** For a fun night, visit [Castle Fun Center](https://www.expedia.ca/Castle-Fun-Center-Hotels.0-l6209270-0.Travel-Guide-Filter-Hotels) in Chester for arcade excitement. If you're in the mood for culture, head to [Paramount Theatre](https://www.expedia.ca/Paramount-Theatre-Hotels.0-l553248621561106035-0.Travel-Guide-Filter-Hotels), 16.1km away, or [Ritz Theater](https://www.expedia.ca/Ritz-Theater-Hotels.0-l553248621558786488-0.Travel-Guide-Filter-Hotels), 25.7km away, both offering a mix of romance, entertainment, and family-friendly shows. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Chester Chester, New York, is a fantastic destination for budget-conscious travellers. Enjoy free activities like visiting Sterling Forest State Park, which adds to your experience without costing a dime. To save on accommodation, consider visiting between January and March, as prices are lower compared to the peak summer months. Booking your stay on a Tuesday can also lead to better rates. For transportation, explore public transit options and consider combining your hotel, flights, and activities through Expedia packages for additional savings. Don't forget to check cancellation policies and recent reviews to ensure a great stay. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are January to March, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and offers, simply arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions near Chester Chester, New York, offers a delightful vacation experience for families and city explorers alike. Visitors can enjoy the natural beauty of nearby national parks, scenic lakes, and urban parks, perfect for outdoor activities and cultural experiences. Don't miss attractions like Chester Park, where you can unwind and take in the local scenery. Whether you're seeking adventure or relaxation, Chester has something to suit every traveller's taste. - **[United States Military Academy: ](https://www.expedia.ca/United-States-Military-Academy-Hotels.0-l6093733-0.Travel-Guide-Filter-Hotels)** Located 22.5km from Chester, this prestigious academy offers a glimpse into military life and education. Visitors can explore its historic campus and learn about the traditions and values that shape future leaders. - **[Bear Mountain State Park: ](https://www.expedia.ca/Bear-Mountain-State-Park-Hotels.0-l6127050-0.Travel-Guide-Filter-Hotels)** Just 24.1km away, this scenic park is perfect for outdoor enthusiasts. With stunning views, hiking trails, and recreational activities, Bear Mountain invites you to immerse yourself in nature's beauty and adventure. - **[Harness Racing Museum and Hall of Fame: ](https://www.expedia.ca/Harness-Racing-Museum-And-Hall-Of-Fame-Hotels.0-l6225670-0.Travel-Guide-Filter-Hotels)** Only 6.4km from Chester, this unique museum celebrates the rich history of harness racing. Engage with interactive exhibits and discover the culture and sportsmanship that define this exciting pastime. ### Best time to go to Chester The best time to visit Chester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.0°F (-2.2°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 37.4°F (3.0°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 48.7°F (9.3°C) | Light Rain | Mostly Sunny | Average | Average | | May | 59.4°F (15.2°C) | Light Rain | Mostly Sunny | Average | Average | | June | 67.6°F (19.8°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 73.9°F (23.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 72.0°F (22.2°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 54.0°F (12.2°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 42.1°F (5.6°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### The nearest major airports for your trip to Chester When planning your visit to Chester, New York, you can choose from three major airports. John F. Kennedy International Airport ([JFK](https://www.expedia.ca/John-F-Kennedy-Intl-Airport-Hotels.0-aJFK-0.Travel-Guide-Filter-Hotels)) is located 90.1km away, with excellent hotel options nearby such as the 5-star [Arlo Williamsburg](https://www.expedia.ca/New-York-Hotels-The-Williamsburg-Hotel.h16007579.Hotel-Information) and [The William Vale](https://www.expedia.ca/New-York-Hotels-The-William-Vale.h11971622.Hotel-Information). Newark Liberty International Airport ([EWR](https://www.expedia.ca/Newark-Liberty-Intl-Airport-Airport-Hotels.0-aEWR-0.Travel-Guide-Filter-Hotels)) is 75.6km away, featuring luxurious accommodations like [The Dominick](https://www.expedia.ca/New-York-Hotels-The-Dominick.h21783007.Hotel-Information) and [The Wall Street Hotel](https://www.expedia.ca/New-York-Hotels-The-Wall-Street-Hotel.h55444869.Hotel-Information), both 14.5km from the airport. LaGuardia Airport ([LGA](https://www.expedia.ca/LaGuardia-Airport-Hotels.0-aLGA-0.Travel-Guide-Filter-Hotels)) is the closest at 74.0km, with top-rated hotels including [Virgin Hotels New York City](https://www.expedia.ca/New-York-Hotels-Virgin-Hotels-New-York-City.h87406830.Hotel-Information) and [The Mark](https://www.expedia.ca/New-York-Hotels-The-Mark.h19712.Hotel-Information), both within 9.7km. Each airport provides convenient access to Chester for a seamless travel experience. ## Frequently asked questions ### What is the best area to stay in Chester? > This area is the heart of Chester, offering a pleasant and convenient experience for visitors. Main Street is lined with local shops, eateries, and historic buildings, creating a welcoming feel. You'll find attractions like the Chester Historical Society Museum and the Sugar Loaf Performing Arts Center nearby. The village is also known for its strong community spirit and regular events. > > > Couples looking for a relaxing getaway will appreciate the village centre. It offers a selection of cosy bed and breakfasts and boutique hotels, providing a more personal touch. You can enjoy strolls through the village, browse antique shops, and dine at local restaurants without needing to drive. The nearby Black Dirt Region is also easily accessible for wine tasting or farm visits, making for enjoyable day trips. > > > For families, staying within the village centre provides easy access to the local parks and ice cream parlours. The village green often hosts community gatherings and is a pleasant spot for children to play. ### What are the best hotels in Chester that travellers recommend? > This hotel, with an 8.6 rating, offers comfortable and clean rooms with premium bedding, ensuring a restful stay. Guests frequently praise the friendly and great staff, as well as the delicious and good complimentary breakfast, including convenient to-go options. The indoor pool is known for being clean, and there are pool sun loungers available for relaxation. The hotel is also located within a shopping district and is just 0.6 km from Castle Fun Centre and 3.2 km from LEGOLAND® New York. ### What are the best family hotels in Chester? > The Holiday Inn Express Hotel & Suites Chester by IHG, with a rating of 8.6, is a highly recommended option for families. Guests frequently mention the friendly staff and delicious complimentary breakfast. The hotel offers comfortable and clean rooms, some with sofa beds and connecting room options, which are ideal for families. A clean pool is also available for guests to enjoy. It is conveniently located just 0.6 km from the Castle Fun Centre and 3.2 km from LEGOLAND® New York. Free self-parking and free WiFi are also provided. > > > Another superb choice is The Dominion House Bed & Breakfast, which boasts an outstanding rating of 9.6\. This accommodation provides amenities such as cribs and a shared children's playground, suiting families. Guests can also benefit from free breakfast, free self-parking, and free wired internet in public areas. Find more [child-friendly accommodations in Chester](https://www.expedia.ca/Chester-Hotels-Family-Hotel.0-0-d6046665-tFamilyHotel.Travel-Guide-Filter-Hotels) ### What hotels in Chester offer free breakfast? > The Dominion House Bed & Breakfast, with an impressive 9.6 rating, provides a delightful free breakfast to start your day. Guests also benefit from complimentary wired internet in public areas, free RV, bus, and truck parking, and free toiletries. > > > Another great option is the Holiday Inn Express Hotel & Suites Chester by IHG, a 3-star hotel with an 8.6 rating. This hotel offers a free breakfast, including a convenient to-go option, along with free self-parking and complimentary wired internet in public areas. Guests frequently praise the friendly staff, delicious breakfast, and comfortable, clean rooms. Find more [hotels with free breakfast in Chester](https://www.expedia.ca/Chester-Hotels-Hotels-With-Free-Breakfast.0-0-d6046665-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) ### What are the best budget hotels in Chester? > The Holiday Inn Express Hotel & Suites Chester by IHG, with an 8.6 rating, offers comfortable and clean rooms, and guests frequently highlight the friendly and great staff. The hotel provides free Wi-Fi, free wired internet in public areas, and complimentary toiletries. A delicious and good breakfast is included, and a to-go breakfast option is also available. Free self-parking is another convenient feature. > > > Another excellent option is The Dominion House Bed & Breakfast, which boasts an impressive 9.6 rating. This charming bed and breakfast provides free wired internet in public areas, free toiletries, and complimentary breakfast. Guests will also appreciate the free self-parking and the availability of free RV, bus, and truck parking. View all [budget hotels in Chester](https://www.expedia.ca/Chester-Hotels-Cheap-Hotels.0-0-d6046665-tCheapHotels.Travel-Guide-Filter-Hotels) ### What are the best hotels in Chester near LEGOLAND® New York? > This hotel, with an 8.6 rating, is conveniently located just 3.2 kilometres from LEGOLAND® New York. Guests frequently praise the friendly and great staff, delicious and good breakfast, and comfortable and clean rooms. It has features friendly for families such as connecting rooms and sofa beds, as well as complimentary breakfast with a to-go option, free self-parking, and free Wi-Fi. The clean pool is also a popular feature. ### When is the best time to go to Chester? > Late spring offers comfortable temperatures, typically ranging from 15°C to 25°C, making it ideal for walking, visiting local farms, and enjoying the natural beauty of the Hudson Valley. The foliage is lush and green, and many local attractions, such as farmers' markets and outdoor events, begin to open for the season. This period is particularly good for solo travellers or couples looking for a relaxed getaway with opportunities for scenic drives and light outdoor recreation without the peak summer crowds. > > > Early autumn provides a spectacular display of fall colours, especially from late September through October, with temperatures usually between 10°C and 20°C. This is a prime time for couples or solo travellers who appreciate picturesque landscapes and outdoor activities like apple picking at local orchards or exploring nearby state parks. The crisp air and vibrant scenery make it a popular time for wine tasting tours at local vineyards. > > > While summer (July to August) is also a popular time with warmer weather for lakes and outdoor adventures, it can be busier and hotter. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chester hotel booking with Expedia? ### How much is the nightly rate at a Chester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near NYC-All Airports ](https://www.expedia.ca/All-Airports-Airport-Hotels.0-aNYC-0.Travel-Guide-Filter-Hotels) - [Hotels near Arrow Park Lake and Lodge ](https://www.expedia.ca/Arrow-Park-Lake-And-Lodge-Hotels.0-l6209262-0.Travel-Guide-Filter-Hotels) - [Bellvale Hotels ](https://www.expedia.ca/Bellvale-Hotels.d3000350681.Travel-Guide-Hotels) - [Cheap Hotels in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - 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