Title: Chester, NY Guest Houses from $84 | 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) ## Check prices for these dates Next weekend [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 two weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-06-05&endDate=2026-06-07&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) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/2d8c93f7.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 (1,003 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 $107 nightly $126 total Apr 12 - Apr 13 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/20000000/19450000/19441300/19441254/98e48046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Primrose) | Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/0c3a1284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/3cff05ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast [](https://www.expedia.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 9 - Apr 10 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) ![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) ![Front of property](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/9bba8a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107260000/107254000/107253932/77332016.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 $75 nightly $84 total Apr 7 - Apr 8 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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/e358b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/c1748f32.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) ### 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 (29 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 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.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) ![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) ### 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 (840 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) ![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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.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 (1,004 reviews) "Amazing stay with great amenities!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Audrey $96 nightly $118 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.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 (1,001 reviews) "Amazing staff Great breakfast Clean quiet rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) R $110 nightly $135 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd.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) ![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 (1,002 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 $91 nightly $108 total Apr 9 - Apr 10 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.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 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Appalachian-Motel.h9665655.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/046baaca.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/ba2c672f.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 (1,007 reviews) "Great stay!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) diana $101 nightly $119 total Apr 12 - Apr 13 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/1000000/50000/42700/42651/e850dcfd.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) ![Business center](https://images.trvl-media.com/lodging/1000000/50000/42700/42651/5922b597.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 $88 nightly $101 total Apr 20 - Apr 21 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Quality-Inn-Near-Mountain-Creek.h42651.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) ![Business center](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/8d141322.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) ### Sleep Inn & Suites Monroe - Woodbury [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) Monroe 9.4/10 Exceptional (1,049 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 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3c808906.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 Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/4c32f4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w1024h680x0y3-a7b1dcac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w904h683x60y0-c79d6146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w906h683x59y0-429ea470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in the heart of the Hudson Valley, Cabin 4 [](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.Hotel-Information) Newburgh 9.0/10 Wonderful (26 reviews) "We LOVE this place and have stayed here twice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer w. $169 nightly $200 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34237/c6f7ce7f.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) ### Days Inn by Wyndham Wurtsboro [](https://www.expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Wurtsboro.h34237.Hotel-Information) Wurtsboro 7.6/10 Good (616 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) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110100000/110091100/110091071/24ae833f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110100000/110091100/110091071/55fe65c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110100000/110091100/110091071/c661a77b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110100000/110091100/110091071/836714f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Inn Steps away from Downtown Warwick only an Hour away from NYC [](https://www.expedia.com/Warwick-Hotels-Charming-Inn-Steps-Away-From-Downtown.h110091071.Hotel-Information) Warwick 9.2/10 Wonderful (21 reviews) "Great location easy access and a nice room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce E. $132 nightly $149 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Warwick-Hotels-Charming-Inn-Steps-Away-From-Downtown.h110091071.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/1000000/10000/2700/2642/117bdbd5.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) ![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) ### Spark by Hilton Fishkill [](https://www.expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) Fishkill 8.0/10 Very Good (53 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 $93 nightly $108 total Apr 28 - Apr 29 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) ![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) ![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 – 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 (1,003 reviews) "Good place, reasonable price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew $106 nightly $120 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Business center](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/d7537d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/5ad4d11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/08c3cc7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking | Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/930000/921600/921510/4029198a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn at Central Valley-Woodbury [](https://www.expedia.com/Newburgh-Hotels-Americas-Best-Value-Inn-Central-Valley.h921510.Hotel-Information) Central Valley 7.2/10 Good (1,001 reviews) "Old " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxana $83 nightly $102 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Americas-Best-Value-Inn-Central-Valley.h921510.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) ![Lobby](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/0b1ff612.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) ### Tru by Hilton Middletown [](https://www.expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) Middletown 8.6/10 Excellent (994 reviews) "Friendly staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magaly $97 nightly $114 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.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=2026-04-20&endDate=2026-04-21®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 ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Very good " [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Courtyard by Marriott Middletown Goshen](https://images.trvl-media.com/lodging/1000000/930000/921500/921424/5a64b5a6_y.jpg) ### Courtyard by Marriott Middletown Goshen 10/10 Excellent "Room was clean, service was prompt, hot tub was a nice surprise!" [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Middletown-Goshen.h921424.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 10/10 Excellent "Clean room" [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/f02832d4_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "The room was very clean. Check in was pleasant and the staff were very helpful. The breakfast included was a plus and very tasteful" [](https://expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![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 "Room was clean, AC did not work at all first night. When we let the front desk know the response was “if it doesn’t work in that room open a window”. They refused to switch us rooms even though we were there multiple nights. " [](https://expedia.com/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e_y.jpg) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 10/10 Excellent "." [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 8/10 Good "Everything is fine " [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/8648b91b_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 8/10 Good "The breakfast was amazing and staff friendly. However this hotel is under construction and paint fumes in the halls. Thankfully not in the room. The dust from the construction was in the rooms. Vacuuming the carpet would’ve been a good idea. After construction I’m sure this hotel would merit 5 stars." [](https://expedia.com/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Hilton Garden Inn Nanuet](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca_y.jpg) ### Hilton Garden Inn Nanuet 8/10 Good "Good" [](https://expedia.com/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) ## Find out more about Chester ## Chester Guest Houses information | Number of reviews | 12,509 | | ----------------- | -------------- | | Accommodation | 6 Guest Houses | | Lowest Price | $84 | | 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) - [Hotels near Castle Fun Center ](https://www.expedia.com/Castle-Fun-Center-Hotels.0-l6209270-0.Travel-Guide-Filter-Hotels) - 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