Title: The Best 2 Star Hotels in Chester, NY from $100 | 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 13 - Mar 14](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-14&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-14&endDate=2026-03-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-03-20&endDate=2026-03-22&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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283.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 (1,127 reviews) "Price reasonable, staff are friendly, good location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marilou $94 nightly $109 total Mar 22 - Mar 23 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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/f7784036.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) ### 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) "Clean room very welcoming staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felicia $104 nightly $122 total Mar 16 - Mar 17 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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/d80f5f9d.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 (1,481 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Omar $99 nightly $114 total Mar 29 - Mar 30 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 (1,067 reviews) "Clean, quiet and great breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn $106 nightly $130 total Mar 23 - Mar 24 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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/bf708146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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 (1,001 reviews) "Friendly staff. Coffee machines at the lobby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vincent $117 nightly $134 total Mar 16 - Mar 17 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) ![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) ![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.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) Nanuet 7.8/10 Good (1,000 reviews) "Room was clean, and comfy. Staff was courteous" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josephine $98 nightly $114 total Mar 22 - Mar 23 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/933a997a.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) ### 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 (1,003 reviews) "Great customer service and breakfast was excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis $105 nightly $121 total Mar 22 - Mar 23 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.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) ### 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 (1,002 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 $96 nightly $109 total Mar 22 - Mar 23 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) ![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) ![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) ### 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 (1,000 reviews) "Nice room breakfast was ok needs to be hot not judt luke warm." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna $98 nightly $116 total Mar 22 - Mar 23 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) ![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) ![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) ### 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 (1,001 reviews) "Wonderful accommodations!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne $114 nightly $135 total Mar 22 - Mar 23 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) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/cabaefdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – 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 (1,002 reviews) "Superb place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denessy $99 nightly $112 total Mar 15 - Mar 16 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, 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) ![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 (1,000 reviews) "The staff was really welcoming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devis $89 nightly $102 total Mar 15 - Mar 16 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 (1,000 reviews) "Very comfortable beds,clean and breakfast was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn $122 nightly $140 total Mar 16 - Mar 17 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/122d16ef.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/a6ffa5e2.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 (1,001 reviews) "Great overall stay, nice restaurant beside hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dale $101 nightly $117 total Mar 22 - Mar 23 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 (1,000 reviews) "Good breakfast, and everything was clean in a great room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $90 nightly $103 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) ![Lobby](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/0b1ff612.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) ### Tru by Hilton Middletown [](https://www.expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) Middletown 8.6/10 Excellent (986 reviews) "Yes I enjoyed my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vivette $103 nightly $122 total Mar 23 - Mar 24 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) ![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/f3b7bb7c.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) ### 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 (832 reviews) "clean, warm room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $88 nightly $100 total Mar 16 - Mar 17 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) ![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 (1,000 reviews) "Everything was exactly what I expected from room cleanliness, pool access, and morning breakfast! Thanks for a great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan $101 nightly $116 total Mar 22 - Mar 23 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) ![Lobby](https://images.trvl-media.com/lodging/1000000/870000/867400/867313/99577371.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) ### 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 $102 nightly $116 total Mar 22 - Mar 23 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) ![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/fe678a50.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) ![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 (1,034 reviews) "Good location and friendly staff, would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Declan $107 nightly $121 total Mar 22 - Mar 23 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 18 - Mar 19 Total with taxes and fees 8.6/10 Excellent! (1,011 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 16 - Mar 17 Total with taxes and fees 8.8/10 Excellent! (754 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 $91 nightly $105 total Mar 21 - Mar 22 Total with taxes and fees 7.8/10 Good! (37 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%2F14%2F2026&endDate=3%2F15%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%2F14%2F2026&endDate=3%2F15%2F2026®ionId=6046665&star=20&star=20&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%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%2F14%2F2026&endDate=3%2F15%2F2026®ionId=6046665&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%2F2026®ionId=6046665&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F14%2F2026&endDate=3%2F15%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=2026-03-27&endDate=2026-03-28&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 ## 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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