Title: Chester, NY Guest Houses from $83 | 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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Chester ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.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) "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 $125 nightly $148 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/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/20000000/19450000/19441300/19441254/3cff05ce.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/f9a6b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast [](https://www.expedia.com/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 $215 nightly $243 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) ![Comfort Room, 2 Double Beds | Iron/ironing board, free WiFi](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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/77332016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 1 Queen Bed | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/8995b312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### High Point Motel [](https://www.expedia.com/Sussex-Hotels-High-Point-Motel.h107253932.Hotel-Information) Sussex 9.2/10 Wonderful (122 reviews) "Amazing easy check in/out and very kind staff. Had a wonderful stay, thank you! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda $74 nightly $83 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Sussex-Hotels-High-Point-Motel.h107253932.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/7ce1352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/61a8edaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/a69379da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/e358b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Central Valley - Woodbury [](https://www.expedia.com/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.Hotel-Information) Central Valley 8.4/10 Very Good (28 reviews) "The hotel is new and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FENGMING $107 nightly $132 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/84f664f7.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) "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 $92 nightly $106 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.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 (1,001 reviews) "Amazing stay with great amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey $98 nightly $121 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/w5746h3937x0y5-10021cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/0bd48f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/046baaca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Middletown Goshen [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) Middletown 8.6/10 Excellent (1,003 reviews) "Great stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) diana $101 nightly $119 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/88d2ecc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/a6849a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/d055a3f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/7eb11b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Middletown [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) Middletown 8.6/10 Excellent (1,001 reviews) "It was a beautiful experience. Clean and 5 star service. The staff so friendly and helpful. Peaceful fun experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda $87 nightly $103 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.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 8.8/10 Excellent (1,001 reviews) "Best Hotel in area so far 😁 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debi $105 nightly $124 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![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) ![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 (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 $95 nightly $107 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/c4928040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed | Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/d71c1690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/w4000h2662x0y0-aa463bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) Goshen 8.8/10 Excellent (1,000 reviews) "Amazing staff Great breakfast Clean quiet rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) R $118 nightly $145 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/32024169.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Desk, laptop workspace, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/0d0877d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/0be7b0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Fishkill [](https://www.expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) Fishkill 7.8/10 Good (50 reviews) "The place was spotless and the staff were very friendly. The bed was so comfortable lovely stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sharon $96 nightly $111 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.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) ![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) ![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) ### 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 (1,008 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) ![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/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 (1,000 reviews) "Wonderful accommodations!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne $114 nightly $135 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Suite, 1 King Bed, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/058ac7ad.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 (1,000 reviews) "Great overall stay, nice restaurant beside hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Dale $101 nightly $117 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/dcfab2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/5191c840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/11731bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9670000/9665700/9665655/96738a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Appalachian Motel [](https://www.expedia.com/Vernon-Hotels-Appalachian-Motel.h9665655.Hotel-Information) Vernon 7.6/10 Good (528 reviews) "Room was clean everything was good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel $75 nightly $86 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Appalachian-Motel.h9665655.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/903ceccc.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) ![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) ### Hampton Inn Harriman Woodbury [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1,083 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 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Suite, 1 King Bed, Non Smoking (1 Bedroom) | In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/2ebdd972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Refrigerator & Microwave | In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/3d926444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/5efb2487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/97f00815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Wurtsboro [](https://www.expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) Wurtsboro 7.6/10 Good (615 reviews) "Everything was clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $106 nightly $120 total May 3 - May 4 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) ![Room, 1 King Bed, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9.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) ![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) ### 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 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2260000/2256600/2256592/d987aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2260000/2256600/2256592/ecf083e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/3000000/2260000/2256600/2256592/1b13bfe2.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/3000000/2260000/2256600/2256592/a4e8201a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Haskell - Wayne Area by IHG [](https://www.expedia.com/Wanaque-Hotels-Holiday-Inn-Express-Haskell-Wayne-Area.h2256592.Hotel-Information) Wanaque 9.0/10 Wonderful (1,000 reviews) "Clean room . Highly recommend great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry $127 nightly $146 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Wanaque-Hotels-Holiday-Inn-Express-Haskell-Wayne-Area.h2256592.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.com/Hotel-Search?startDate=2026-04-16&endDate=2026-04-17®ionId=6046665&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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%2FChester-Guest-Houses.d6046665-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Guest-Houses.d6046665-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg) ### Courtyard by Marriott Newburgh Stewart Airport 2/10 Terrible "Only one pool Available and the rooms Wjere freezing " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/38c7288e_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 8/10 Good "šŸ‘" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 8/10 Good "Staff was awesome! Loved the shuttle to Woodbury Common." [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Hilton Garden Inn Nanuet](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca_y.jpg) ### Hilton Garden Inn Nanuet 10/10 Excellent "Clean room, a little dated" [](https://expedia.com/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 2/10 Terrible "Hotel was under renovation. We were informed prior that the pool was under renovation but not the entire hotel. Most of the 3rd floor was under construction. There were rooms on the second floor under construction. The carpets were dirty and WiFi was intermittent. Front desk was helpful and allowed us to cancel our reservation and provided a full refund. Perhaps it will be better in the future. " [](https://expedia.com/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Great hotel. Highly recommend." [](https://expedia.com/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c_y.jpg) ### Overlook Lodge at Bear Mountain 4/10 Poor "Bathroom toilet was not cleaned nor flushed. Someone had used it, not flushed. My 5 year old daughter went in as soon as we walked in the room and told us about it. I was offered to change rooms which meant I would have had to drive another mile back to the main lobby to get new card. I decided to clean the toilet and flush it myself. VERY bad, yet a simple thing that should not occur." [](https://expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 8/10 Good "Parking was easy, breakfast was fine, room was clean." [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/d3089562_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "The room was clean the bed was comfortable the staff was friendly & amazing " [](https://expedia.com/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ## Find out more about Chester ## Chester Guest Houses information | Number of reviews | 15,556 | | ----------------- | -------------- | | Accommodation | 6 Guest Houses | | Lowest Price | $83 | | Highest Price | $243 | ## Frequently asked questions ### What is the nightly rate for a guest house in Chester? ### What's the difference between a Chester guest house and a B&B? ## 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) - 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