Title: Book the Best ADVENTURE Hotels in Chester in 2025 | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Chester, NY from CA $144 - ![](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 availability on Chester Hotels & Resorts for Couples Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Hotels & Resorts for Couples ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.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) ![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/dc5981dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG Montgomery 8.8/10 Excellent (780) "Super clean and breakfast was amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuneiry CA $151 CA $176 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/d11440c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/3770735e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/667bc407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/480000/473500/473490/c09894ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western The Inn At Ramsey Ramsey 7.2/10 Good (1007) "When the manager saw how much luggage we had he moved our room closer for our convience. So thoughtful!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Robin CA $125 CA $144 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Ramsey-Hotels-Best-Western-The-Inn-At-Ramsey.h473490.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/b3546f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/w4000h2662x0y0-618f3f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/2a01f3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Newburgh Stewart Airport Newburgh 8.2/10 Very good (691) "Property clean rooms clean front desk the Best " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dirwin CA $142 CA $168 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/fef382d4.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/70000000/69540000/69532700/69532688/1dc5d583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/d7e6e4ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69540000/69532700/69532688/6b59c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax! Wallkill 10/10 Exceptional (69) "The property was just as pictured, and a convenient off site " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen S. CA $156 CA $322 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Wallkill-Hotels-Waterfront-Modern-1bd-10-Min-To-Mtns-Wineries.h69532688.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/b3c97637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/24798174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/877cc95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/fd01a6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dream getaway apartment in the foot of Gunks Ridge Wallkill 9.6/10 Exceptional (23) "This was such a great option for us as we were only in town for the night for a haunted house attraction. The space is extremely spacious, very nicely decorated and gave us the fall season feeling. A great stay and would definitely do it again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal L. CA $105 CA $258 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119810000/119809900/119809853/5e8d6953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119810000/119809900/119809853/69c55825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/120000000/119810000/119809900/119809853/3bbb122a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119810000/119809900/119809853/b851f01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRANQUIL MOUNTAIN SOLITUDE Pine Bush 10/10 Exceptional (4) "Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle H. CA $154 CA $286 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Pine-Bush-Hotels-TRANQUIL-MOUNTAIN-SOLITUDE.h119809853.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/5d69e9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/c67996db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/669fa011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/986000/985904/ef6c4690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Nanuet Nanuet 7.8/10 Good (1007) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $156 CA $181 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Nyack-Hotels-Hilton-Garden-Inn-Nanuet.h985904.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/0c0edcb5.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/1000000/120000/119300/119273/8529e0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/w3831h2553x9y7-9c25ee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1000) "Was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $165 CA $187 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w905h683x60y0-cdd484b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w905h683x60y0-c45540b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w1024h680x0y3-176c2109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/91000000/90900000/90899300/90899226/w450h683x287y0-a114e4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in the heart of the Hudson Valley, Cabin 2 Newburgh 9.4/10 Exceptional (27) "This cabin was the perfect size. Clean, private, and made me feel safe and secure. Easily accessible. I would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maryann B. CA $153 CA $247 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899226.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/116000000/115820000/115810500/115810455/5f68ec93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115820000/115810500/115810455/b10cecf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115820000/115810500/115810455/02657921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/116000000/115820000/115810500/115810455/381786c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234 Vernon Township 10/10 Exceptional (7) "The room was spotless. There was no staff that we could identify. We had a problem accessing the room at first and there was no one to ask for help. We eventually were able to enter the code to the room and enter" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ira CA $176 CA $379 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Vernon-Hotels-Cozy-Condo-1-Bedroom-1-Bathroom-1-Kitchenette.h115810455.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=2025-11-19&endDate=2025-11-20®ionId=6046665&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](//images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Friendly staff, easy checkin and clean room! I’ve stayed here twice this year (2025) and wasn’t disappointed. " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Hampton Inn & Suites Mahwah](//images.trvl-media.com/lodging/4000000/3560000/3555900/3555820/c56a5aff_y.jpg) ### Hampton Inn & Suites Mahwah 10/10 Excellent "Ok" [](https://expedia.ca/Mahwah-Hotels-Hampton-Inn-Suites-Mahwah.h3555820.Hotel-Information) ![Hampton Inn Nanuet](//images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb_y.jpg) ### Hampton Inn Nanuet 10/10 Excellent "Fresh breakfast and quiet rooms. Very personable staff at front desk!" [](https://expedia.ca/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Residence Inn by Marriott Saddle River](//images.trvl-media.com/lodging/1000000/900000/892900/892852/55c60c22_y.jpg) ### Residence Inn by Marriott Saddle River 10/10 Excellent "Staff was friendly and accommodating. We needed to extend our stay for another day and they were happy to help us. " [](https://expedia.ca/Saddle-River-Hotels-Residence-Inn-By-Marriott-Saddle-River.h892852.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 "staff was very helpful and the view was very nice" [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](//images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "Clean room " [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![DoubleTree by Hilton Mahwah](//images.trvl-media.com/lodging/1000000/30000/21000/20986/2c7b4ca0_y.jpg) ### DoubleTree by Hilton Mahwah 10/10 Excellent "I arrived with a broken ankle and the staff went above and beyond to make my stay more comfortable. " [](https://expedia.ca/Mahwah-Hotels-DoubleTree-By-Hilton-Mahwah.h20986.Hotel-Information) ![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 "." [](https://expedia.ca/Nyack-Hotels-Crowne-Plaza-Suffern-Mahwah.h2358.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 "Clean room, comfortable bed, staff very friendly. No complaints at all!" [](https://expedia.ca/Ramsey-Hotels-Holiday-Inn-Express-Ramsey-Mahwah.h4613.Hotel-Information) ## Frequently asked questions ### How much do hotels for couples in Chester cost? > Hotels for couples in Chester range between CA $144 and CA $379 per night. These stays provide quality time with your sweetheart at a price that's easy on your wallet. 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. ### What are the best hotels for couples in Chester? > A traveller favourite is [Residence Inn by Marriott Middletown Goshen](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information). Make yourself comfortable at this 3-stars escape which offers a swimming pool and a firepit. [Home2 Suites by Hilton Middletown](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.Hotel-Information) is another recommended hotel for couples. Pick up a deal at this 3-stars option and make the most of handy amenities which include a terrace and a firepit. You can pick from multiple hotels for couples in Chester with a total average guest review rating of 8.9. ### How many hotels for couples are there in Chester? > Chester has 3 hotels for couples. To help you book a stay that's right for you, use our handy filters to search for must-have perks and amenities. Make your next getaway with your sweetheart the best yet with Expedia! ### Why book your hotel for couples in Chester with Expedia? > Booking a hotel for couples in Chester is as easy as entering your travel dates and picking the option that's perfect for misty-eyed lovebirds. From low-priced motels and all-inclusive resorts to luxurious retreats packed with romantic features, Expedia has digs for all tastes. As for attractive deals? They're only a click away! ### How can I find cheap hotels for couples in Chester? > An excellent way to uncover cheap hotels for couples in Chester is with Expedia's handy filter tool. Fine-tune your search results by amenities, star rating and budget and land awesome deals on accommodations where you can chill out with your partner. ### What is there to do in Chester near my hotel for couples? > Once you've unpacked your bags and settled in, head out and discover the wonderful things Chester has for you to experience. 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