Title: Chester Cottages from CA $302 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Black dirt region farm Chester New York](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chester Cottage Rentals from CA $302 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Cottages ![Children's area](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/7c6456ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/5c45b185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/b2f29274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Goshen 9.8/10 Exceptional (11) "Overall Great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick H. CA $207 CA $409 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/635322f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/538ca0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114370000/114369800/114369793/12857716.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/a8a63147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Westbrookville CA $231 CA $430 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Hike-Fish-Outdoor-Retreat-On-The-Basher-Kill.h114369793.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) ![Property grounds](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/08a3846a.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) ![Interior](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/2ca37619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Putnam Valley 9.8/10 Exceptional (22) "Great, clean house, nice accommodating host. Would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather T. [](https://www.expedia.ca/Putnam-Valley-Hotels-Cottage-Getaway-DogFriendly.h91391396.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/2b9a9f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/5de49e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/700675ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/d4499593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bloomingburg 10/10 Exceptional (1) "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. CA $196 CA $302 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.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) ![Pool](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3378h2246x65y117-b9d7217d.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/w1288h860x2y0-c486b7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Vernon Township 8.8/10 Excellent (3) "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. CA $314 CA $668 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w907h683x58y0-12eb76e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w906h683x59y0-c9ca3261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w508h683x258y0-c8dc4261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w905h683x60y0-28eafa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Middletown 9.6/10 Exceptional (5) "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. CA $227 CA $584 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Middletown-Hotels-Hello-Small-Stone.h99261544.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) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Fort Montgomery 9.8/10 Exceptional (129) "It has an incredible mountain and water view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MIHYUN CA $263 CA $430 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.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.ca/Hotel-Search?startDate=2025-12-17&endDate=2025-12-18®ionId=6046665&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=VACATION_HOME) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=COTTAGE) Condos [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CONDO) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CABIN) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+New+York%2C+United+States+of+America®ionId=6046665&latLong=41.362595%2C-74.271263&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6046665-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Cottages.d6046665-aaCottages.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Staff great room very clean " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Hampton Inn Nanuet](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "Staff was great and so was the room" [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Hampton Inn & Suites Mahwah](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Excellent stay. Wonderful staff!" [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Great , no complaints. " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](https://images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "All good " [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Courtyard by Marriott Montvale](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/5623b54c_y.jpg) ### Courtyard by Marriott Montvale 10/10 Excellent "Could use more towel hooks or racks. " [](https://expedia.ca/Montvale-Hotels-Courtyard-By-Marriott-Montvale.h21786.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "Clean, courteous and welcoming. " [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Front desk. Person very pleasant" [](https://expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Great hotel - beautiful property, comfortable accommodation, fireplace in cottage and scenic views from balcony " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ## Find out more about Chester ## Chester Cottages information | Number of reviews | 150 | | --- | --- | | Accommodation | 79 Cottages | | Lowest Price | CA $302 | | Highest Price | CA $668 | ## Frequently asked questions ### How much do cottages in Chester cost? > Prices for cottages in Chester range between CA $302 and CA $668 per night. Whatever your budget, you're sure to find an ideal place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Why book your cottage in Chester with Expedia? > Booking a cottage in Chester is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We've have them as well! ### How can I find cheap cottages in Chester? > With Expedia's useful filter tool, scoring cheap cottages in Chester is a snap. To find properties that'll make your hip pocket happy, refine your search by amenities, star rating and budget. ### What is there to do in Chester near my cottage? > Once you've settled into your hotel, head out and discover the wonderful things Chester has on offer. 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