Title: Chester, NY Cottage Rentals from $214 | 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 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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6046665&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester cottages ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/d5ed89f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Living area](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/780cac79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/18ffe7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/a309408b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hike & Fish: Outdoor Retreat Near Trails [](https://www.expedia.com/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information) Westbrookville $272 nightly $308 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/c55e3667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (134 reviews) "Amazing place Thanks for the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien C. $269 nightly $269 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/3008d822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/eb48d384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/54004000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) Goshen 9.8/10 Exceptional (13 reviews) "Great place to stay when visiting Legoland. Convenient location and comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica C. $281 nightly $293 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/e74463e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/13d8fc7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/0f1e7af8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/99922af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk-to-Lake Cottage With Office for Quiet Days and Easy Work [](https://www.expedia.com/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information) Putnam Valley 9.8/10 Exceptional (23 reviews) "Great, clean house, nice accommodating host. Would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather T. $452 nightly $498 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Putnam-Valley-Hotels-Walk-To-Lake-Cottage-With-Office-For-Quiet-Days-And-Easy-Work.h91391396.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w919h683x47y0-1b7c08f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-6b740411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w905h683x60y0-1d21c342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-81ebd497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hello Small Stone [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) Middletown 9.6/10 Exceptional (5 reviews) "The house was great. It was nice to sit and relax by the small pond in the back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John H. $369 nightly $417 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3379h2254x65y113-3bf6be6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/70357fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w2352h3136x64y187-6f5dc167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3378h2246x65y117-b9d7217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) Vernon Township 8.8/10 Excellent (3 reviews) "House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cherlyn I. $423 nightly $478 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/5de49e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/6a029a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/ffdabe30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/bb223671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.Hotel-Information) Bloomingburg 10/10 Exceptional (1 review) "The place was as described, quaint, clean, no issues with communication or check in" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen H. $190 nightly $214 total Apr 17 - Apr 18 Total with taxes and fees [](https://www.expedia.com/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APART_HOTEL) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VILLA) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CHALET) ![](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-Cottages.d6046665-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6046665-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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) ![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 "Check-in went super smooth, breakfast was great! I was expecting continental but hot food was available both weekend days. The high light was the patience the night staff had when faced with a challenging group. Manager Claudine is a Leader in the building I saw her supporting staff while assuring us our stay will be great." [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.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) ![Spark by Hilton Fishkill](https://images.trvl-media.com/lodging/1000000/10000/2700/2642/b112328f_y.jpg) ### Spark by Hilton Fishkill 10/10 Excellent "Room was clean but very minimalist. Not much furniture. No refrigerator. Offered 24 hour coffee and tea. Daily free newspaper. Nice breakfast. Friendly staff." [](https://expedia.com/Fishkill-Hotels-Spark-By-Hilton-Fishkill.h2642.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9_y.jpg) ### Sonesta Simply Suites Nanuet 8/10 Good "Love the kitchen in the room. " [](https://expedia.com/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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 10/10 Excellent "U" [](https://expedia.com/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Crowne Plaza Suffern - Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/ae4d02f3_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "Clean building and lovely staff. " [](https://expedia.com/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great place. Clean room, good breakfast options, good facility. Highly recommend." [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 179 | | ----------------- | ----------- | | Accommodation | 79 Cottages | | Lowest Price | $214 | | Highest Price | $498 | ## Frequently asked questions ### How much do cottages in Chester cost? ### Why book your cottage in Chester with Expedia? ### How can I find cheap cottages in Chester? ### What is there to do in Chester near my cottage? ## 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 LEGOLAND® New York ](https://www.expedia.com/LEGOLAND-New-York-Hotels.0-l553248635997928006-0.Travel-Guide-Filter-Hotels) - 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