Title: The Best 2 Star Hotels in Chester, NY from $102 | 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 24 - Mar 25](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-24&endDate=2026-03-25&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 25 - Mar 26](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-25&endDate=2026-03-26&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-27&endDate=2026-03-29&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) ## 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) ![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) ![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) ### Sonesta Simply Suites Nanuet [](https://www.expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) Nanuet 8.4/10 Very Good (1,139 reviews) "Price reasonable, staff are friendly, good location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilou $97 nightly $113 total Apr 5 - Apr 6 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) ![Efficiency, Suite, 1 King Bed, Non Smoking | Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/6eb13bf8.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 (1,003 reviews) "Best Hotel in area so far šŸ˜ " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debi $101 nightly $119 total Mar 31 - Apr 1 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) ![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) ![Pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/83881d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/d80f5f9d.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 (1,494 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Omar $119 nightly $137 total Apr 19 - Apr 20 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/709ff346.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 (1,076 reviews) "Hotel was very clean and well maintained " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen $106 nightly $130 total Mar 30 - Mar 31 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/1000000/10000/4700/4613/982800a7.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) ### 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 (1,000 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 $117 nightly $134 total Mar 29 - Mar 30 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/a3d8c842.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) ### Hampton Inn Nanuet [](https://www.expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) Nanuet 7.8/10 Good (1,009 reviews) "Bed was a little soft for my taste" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth $98 nightly $114 total Mar 29 - Mar 30 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) ![Buffet](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/830db074.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/38e2c556.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 (1,004 reviews) "really nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shadaya $112 nightly $130 total Mar 30 - Mar 31 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.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) "Great staff and clean rooms. Beautiful views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee $96 nightly $109 total Mar 30 - Mar 31 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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.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) ### 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 (1,006 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 $113 nightly $134 total Mar 29 - Mar 30 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) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/e34f60f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3c808906.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) ### 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 (1,004 reviews) "Wonderful accommodations!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne $114 nightly $135 total Mar 30 - Mar 31 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 (1,000 reviews) "Superb place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denessy $99 nightly $112 total Mar 25 - Mar 26 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) ![Standard Room | View from room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b5096992.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/6d06d46a.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 (1,007 reviews) "Everything is good..but the furnitures need to repair.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chowdhury $89 nightly $102 total Mar 29 - Mar 30 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/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58c34815.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 (1,002 reviews) "Clean room and nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $131 nightly $150 total Mar 30 - Mar 31 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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/a6ffa5e2.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 (1,005 reviews) "Great overall stay, nice restaurant beside hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dale $99 nightly $114 total Apr 5 - Apr 6 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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/e9045f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/84f664f7.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) ### Quality Inn near Mountain Creek [](https://www.expedia.com/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) Vernon 7.6/10 Good (1,006 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 $106 total Mar 29 - Mar 30 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) ![Reception](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/626dc529.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 (990 reviews) "Friendly staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magaly $100 nightly $118 total Apr 5 - Apr 6 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/f3b7bb7c.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.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (836 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) ![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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/23000000/22940000/22934500/22934426/202f6398.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 9.2/10 Wonderful (1,003 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 $106 nightly $123 total Mar 30 - Mar 31 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/450c138b.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) "spotless room and front desk was very sweet! thank you for a great stay this weekend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kai $106 nightly $122 total Mar 31 - Apr 1 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) ![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/fe678a50.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 (1,041 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 Mar 31 - Apr 1 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 $93 nightly $109 total Mar 29 - Mar 30 Total with taxes and fees 8.6/10 Excellent! (1,008 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 $101 nightly $114 total Mar 30 - Mar 31 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 $96 nightly $111 total Apr 2 - Apr 3 Total with taxes and fees 7.8/10 Good! (45 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=3%2F25%2F2026&endDate=3%2F26%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=3%2F25%2F2026&endDate=3%2F26%2F2026®ionId=6046665&star=20&star=20&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F25%2F2026&endDate=3%2F26%2F2026®ionId=6046665&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F25%2F2026&endDate=3%2F26%2F2026®ionId=6046665&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F25%2F2026&endDate=3%2F26%2F2026®ionId=6046665&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F25%2F2026&endDate=3%2F26%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=2026-04-07&endDate=2026-04-08&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 10/10 Excellent "The place is clean every time I come and outstanding customer service" [](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. Take advantage of the 2 Star Hotel availability and easy-going atmosphere. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Castle Fun Center ](https://www.expedia.com/Castle-Fun-Center-Hotels.0-l6209270-0.Travel-Guide-Filter-Hotels) - [Hotels near Museum Village ](https://www.expedia.com/Museum-Village-Hotels.0-l553248621559142200-0.Travel-Guide-Filter-Hotels) - [Hotels near LEGOLANDĀ® New York ](https://www.expedia.com/LEGOLAND-New-York-Hotels.0-l553248635997928006-0.Travel-Guide-Filter-Hotels) - [Hotels near The Rock Sports Complex ](https://www.expedia.com/The-Rock-Sports-Complex-Hotels.0-l553248624556330411-0.Travel-Guide-Filter-Hotels) - [Hotels near Goosepond Mountain State Park ](https://www.expedia.com/Goosepond-Mountain-State-Park-Hotels.0-l553248635974861777-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sugar Loaf ](https://www.expedia.com/5Star-Sugar-Loaf-Hotels.s50-0-d6171726.Travel-Guide-Filter-Hotels) - 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