Title: Book the Best ROMANTIC Hotels in Chester, NY from CA $162 - Chester Romantic Getaways | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/romantic.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Chester, NY from CA $162 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chester Romantic Hotels Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-04&endDate=2025-10-05&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-05&endDate=2025-10-06&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Romantic Hotels ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.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) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.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 Bear Mountain 8.4/10 Very good (1001) "Wonderful staff!" CA $168 CA $191 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hanlon Suite | Children's theme room](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/05c3d7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/91f0a8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn Montgomery 9.2/10 Wonderful (128) "Unique experience, very comfortable, clean and quaint" CA $143 CA $162 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/b675c11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/61f4bfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2400/2358/ae4d02f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Suffern - Mahwah by IHG Suffern 8.8/10 Excellent (1008) "The hotel is good." CA $153 CA $179 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![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) ![Indoor spa tub](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/87db9055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19450000/19441300/19441254/98e48046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dominion House Bed & Breakfast Chester 9.2/10 Wonderful (229) "Amazing hospitality," CA $300 CA $339 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Newburgh-Hotels-The-Dominion-House-Bed-Breakfast.h19441254.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/5623b54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/w3998h2667x0y0-ce547fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/ad434239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/28857133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Montvale Montvale 8.6/10 Excellent (615) "Great stay " CA $193 CA $222 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Montvale-Hotels-Courtyard-By-Marriott-Montvale.h21786.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:30 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/800/736/8e33505f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/800/736/13a47184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Nanuet Nanuet 8.8/10 Excellent (1001) "Staff was really friendly" CA $177 CA $206 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/023ab9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/d09a0803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Thayer Hotel at West Point West Point 9.0/10 Wonderful (625) "We had a wonderful time staying here. Friendly staff and most of all a historic building." CA $272 CA $345 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/2c7b4ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/dd17ff0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/96db1dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21000/20986/81dffb3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Mahwah Mahwah 7.8/10 Good (884) "Staff was wonderful. The stay was good " CA $165 CA $189 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Mahwah-Hotels-DoubleTree-By-Hilton-Mahwah.h20986.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16200000/16199600/16199528/7e3cbba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16200000/16199600/16199528/3a7e4e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16200000/16199600/16199528/0be89258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16200000/16199600/16199528/7b34f208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Fishkill Fishkill 9.6/10 Exceptional (989) "OVERALL STAY WAS GREAT " CA $257 CA $290 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-SpringHill-Suites-By-Marriott-Fishkill.h16199528.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/9a478c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/faaa88f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/2fad5b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/09797bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Middletown Goshen Middletown 9.4/10 Exceptional (309) "Room and service were excellent." CA $232 CA $274 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.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=2025-10-18&endDate=2025-10-19®ionId=6046665&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Crowne Plaza Suffern - Mahwah by IHG](//images.trvl-media.com/lodging/1000000/10000/2400/2358/e31233cf_y.jpg) ### Crowne Plaza Suffern - Mahwah by IHG 10/10 Excellent "it was clean, well-kept and quiet. nothing to complain" [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.Hotel-Information) ![Overlook Lodge at Bear Mountain](//images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "Great natural setting. Comprehensive facilities." [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Holiday Inn Express Ramsey-Mahwah by IHG](//images.trvl-media.com/lodging/1000000/10000/4700/4613/97efb314_y.jpg) ### Holiday Inn Express Ramsey-Mahwah by IHG 10/10 Excellent "The breakfast was great" [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ![Best Western The Inn At Ramsey](//images.trvl-media.com/lodging/1000000/480000/473500/473490/d11440c9_y.jpg) ### Best Western The Inn At Ramsey 10/10 Excellent "Clean and comfortable rooms, friendly staff and a really nice hot breakfast." [](https://expedia.ca/Ramsey-Hotels-Best-Western-The-Inn-At-Ramsey.h473490.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chester? > Are you and your partner looking for a romantic vacation? Our guests also enjoy Chester for its restaurants and shopping. If you want to explore the area, you might head to Castle Fun Center, The Rock Sports Complex, or Museum Village. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Chester? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### What is there to do in Chester? > There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Chester has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Chester for its shopping. A visit to Castle Fun Center, The Rock Sports Complex, or Museum Village might be just the ticket when you're checking out the sights. ### What's the best way to get to Chester and around town during my romantic getaway? > This information about transportation options in Chester might help your romantic trip get off to a smooth start: To get to Chester, book a flight to Stewart Intl. Airport (SWF), which is the closest major airport, located 13.5 mi (21.7 km) from the city center. 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