Title: The Best 2 Star Hotels in Chester, NY from $105 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6046665)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6046665.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 2 Star Hotels Tonight [Mar 31 - Apr 1](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-31&endDate=2026-04-01&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 1 - Apr 2](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-01&endDate=2026-04-02&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester 2-star hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283.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) ![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.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) Nanuet 8.4/10 Very Good (1,146 reviews) "Great Stay Would Definitely Stay Again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antwon $95 nightly $111 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Free continental breakfast on weekdays](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474.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) ![Indoor pool](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/f7784036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1cbd6222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middletown - Goshen [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) Middletown 8.6/10 Excellent (1,006 reviews) "Best Hotel in area so far šŸ˜ " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debi $110 nightly $130 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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) ![Pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/83881d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/d42d0aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Accessible, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/496420ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Mahwah [](https://www.expedia.com/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) Mahwah 8.8/10 Excellent (1,496 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Omar $105 nightly $121 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed Studio | Living area | 55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/7a9acd26.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) ![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 [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1,081 reviews) "Hotel was very clean and well maintained " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen $114 nightly $140 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/d3089562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/c2b6fd57.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/982800a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Ramsey-Mahwah by IHG [](https://www.expedia.com/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) Ramsey 9.2/10 Wonderful (1,006 reviews) "The check in process was quick and easy. Everything was nicely lit and clean. There are restaraunts within walking distance. It is a busy area but worth the stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathryn $114 nightly $131 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.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) ![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) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/e52257ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Nanuet [](https://www.expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) Nanuet 7.8/10 Good (1,004 reviews) "The room was clean, staff was friendly and breakfast was good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mirna $98 nightly $114 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e.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) ![Buffet](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/830db074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/933a997a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG [](https://www.expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) Fishkill 8.4/10 Very Good (1,005 reviews) "really nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shadaya $118 nightly $136 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.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) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.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) ### Overlook Lodge at Bear Mountain [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very Good (1,003 reviews) "Amazing stay with great amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey $93 nightly $105 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![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) ![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) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/1a5890e9.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) ### Holiday Inn Express Hotel & Suites Chester by IHG [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) Chester 8.6/10 Excellent (1,007 reviews) "We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth $121 nightly $143 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3c808906.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/18000000/17270000/17262200/17262186/000bcb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Newburgh Stewart Airport [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) Newburgh 9.2/10 Wonderful (1,006 reviews) "Wonderful accommodations!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne $114 nightly $135 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking, Lake View | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/ae84ea2c.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) ![Suite, 1 King Bed, Accessible, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38401260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh ā€“ Stewart Airport/ West Point [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) New Windsor 8.4/10 Very Good (1,006 reviews) "Good place, reasonable price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew $106 nightly $120 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/6d06d46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds | Desk, blackout drapes, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b8252450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/8e38c0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Hudson [](https://www.expedia.com/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) Peekskill 7.0/10 Good (1,006 reviews) "Everything is good..but the furnitures need to repair.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chowdhury $94 nightly $108 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.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/ab21b3e2.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/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG [](https://www.expedia.com/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) Peekskill 9.2/10 Wonderful (1,004 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer $135 nightly $154 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/ae7fe4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/5daef0cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/122d16ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/a633421f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Fishkill South near I-84 [](https://www.expedia.com/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) Fishkill 9.0/10 Wonderful (1,004 reviews) "Great overall stay, nice restaurant beside hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dale $102 nightly $118 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/e850dcfd.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/dbf205dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/5922b597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/e9045f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn near Mountain Creek [](https://www.expedia.com/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) Vernon 7.6/10 Good (1,002 reviews) "A lot to do over there, good for a whole weekend, or even more. Had great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) illay $93 nightly $107 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) ![Free daily English breakfast](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/ea33701a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/673693a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/0b1ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Middletown [](https://www.expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) Middletown 8.6/10 Excellent (991 reviews) "Friendly staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magaly $99 nightly $117 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.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) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.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) ### Holiday Inn Express & Suites Montgomery by IHG [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (837 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 $96 nightly $109 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/bd8a5a7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/98c02dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking | Egyptian cotton sheets, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/c1ec465c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/fb2f4151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Fishkill near Interstate 84 [](https://www.expedia.com/Poughkeepsie-Hotels-Comfort-Suites-Fishkill-Near-Interstate-84.h22934426.Hotel-Information) Fishkill 9.0/10 Wonderful (1,002 reviews) "Great team and nice place to stay for the price. Definitely am staying here again as I travel for business. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brennan $102 nightly $118 total Apr 21 - Apr 22 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Comfort-Suites-Fishkill-Near-Interstate-84.h22934426.Hotel-Information) ![Studio, 1 Queen Bed, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/c21c6c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/c0f1add0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/450c138b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed, Non Smoking | Private kitchen | Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/e7da7a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites Ramsey Upper Saddle River [](https://www.expedia.com/Ramsey-Hotels-Extended-Stay-America-Suites-Ramsey-Upper-Saddle-River.h867313.Hotel-Information) Ramsey 6.8/10 (1,000 reviews) "Very nice place to stay, quiet and animal friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier $105 nightly $120 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Ramsey-Hotels-Extended-Stay-America-Suites-Ramsey-Upper-Saddle-River.h867313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/de7f38a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/1e19e7e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/8d141322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/8cf6bfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Monroe - Woodbury [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) Monroe 9.4/10 Exceptional (1,046 reviews) "Wonderful staff, clean and perfect for family, business or leisure stay. And budget friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jawanda $101 nightly $114 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Chester-Hotels.s20-0-d6046665.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Chester-Hotels.s20-0-d6046665.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Chester. ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Courtyard by Marriott Middletown Goshen 24 Crystal Run Xing Middletown NY $105 nightly $125 total Apr 26 - Apr 27 Total with taxes and fees 8.6/10 Excellent! (1,002 reviews) [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Courtyard by Marriott Fishkill](https://images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Courtyard by Marriott Fishkill 17 Westage Drive Fishkill NY $121 nightly $137 total Apr 5 - Apr 6 Total with taxes and fees 8.8/10 Excellent! (760 reviews) [](https://expedia.com/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.Hotel-Information) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Spark by Hilton Fishkill 20 Schuyler Blvd Fishkill NY $98 nightly $113 total Apr 7 - Apr 8 Total with taxes and fees 7.8/10 Good! (48 reviews) [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) Still don't see what you're looking for? [See all properties in Chester.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20&star=20&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=4%2F1%2F2026&endDate=4%2F2%2F2026®ionId=6046665&star=20&star=20&amenities=WATER_PARK) 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. ## 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 Center for go-karts, mini-golf, and arcade games. [See all hotels in Chester](https://www.expedia.com/Hotel-Search?startDate=2026-04-14&endDate=2026-04-15&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 ![Red Roof Inn & Suites Newburgh ā€“ Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh ā€“ Stewart Airport/ West Point 8/10 Good "Good" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ## Find out more about Chester When you've got to get away to a new or favorite destination without breaking the bank, Chester awaits with convenient 2 Star hotels and a change of scenery. Stay on your feet visiting top attractions that draw of visitors, or settle in for a hot cuppa nearby and relax. You're about to find out why both locals and travelers love this place. ### The Perfect Accommodation at the Perfect Price 2 Star hotels are in high demand in Chester. You'll find the best deals right here, so book early and save on a great getaway. Thanks to budget-friendly prices and traveler-friendly amenities, you'll find a place to stay that's just right for you. Stay here and be one of the first guests to post a review and share your thoughts. So, savor the comfort of a well-kept room and attentive hospitality. When you book with Expedia, you can stay all over the world, and the jet-setting starts in Chester. ### Reserve a Two-Star 2 Star Hotel Today! Plan your trip to Chester now with Expedia's easy online travel booking and start relaxing before you even leave the house. If you need a break from the crowds, you may find that this region offers just the reprieve you've been looking for. 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