Title: Book the Best ROMANTIC Hotels in New Windsor, NY from CA $162 - New Windsor Romantic Getaways | Expedia.ca [Hotels in New Windsor](https://expedia.ca/New-Windsor-Hotels.d10021.Travel-Guide-Hotels)[Vacation Rentals in New Windsor](https://expedia.ca/New-Windsor-Vacation-Rentals.d10021.Travel-Guide-VacationRentals)[Things to do in New Windsor](https://expedia.ca/Things-To-Do-In-New-Windsor.d10021.Travel-Guide-Activities)[New Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-New-Windsor.d10021.Car-Rental-Guide)[New Windsor Vacation Packages](https://expedia.ca/New-Windsor.d10021.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6747dae34f8ec5459e58210202f4caed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Wanderlustfemale # Find Romantic Hotels in New Windsor, NY from CA $162 ![](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 New Windsor Romantic Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-14&endDate=2025-10-15&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-15&endDate=2025-10-16&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top New Windsor 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) ![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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain Bear Mountain 8.4/10 Very good (1014) "Clean room, easy parking" CA $145 CA $165 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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) ![Street view](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/996a16d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Thayer Hotel at West Point West Point 9.0/10 Wonderful (636) "We had a wonderful time staying here. Friendly staff and most of all a historic building." CA $221 CA $287 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/61bfd00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/c4e21282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/6b3ae78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Poughkeepsie by IHG Poughkeepsie 8.6/10 Excellent (1010) "Friendly staff and excellent breakfast. " CA $139 CA $162 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed | Private kitchen](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/941154e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Mountain View | Living area](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/78e69393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/025b23c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Poughkeepsie Convention Center Downtown Poughkeepsie 8.4/10 Very good (1016) "Over all it is a nice hotel to stay." CA $154 CA $181 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/3c35a288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/27c83ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/2f1506bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/16000000/15990000/15984700/15984645/74396b43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Middletown Middletown 9.0/10 Wonderful (730) "the room was very clean, friendly staff " CA $183 CA $221 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Home2-Suites-By-Hilton-Middletown.h15984645.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) ![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) ![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) ### Borland House Inn Montgomery 9.2/10 Wonderful (133) "Unique experience, very comfortable, clean and quaint" CA $144 CA $163 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.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) ![Reception](https://images.trvl-media.com/lodging/49000000/48280000/48273100/48273068/09797bb4.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) ### Residence Inn by Marriott Middletown Goshen Middletown 9.4/10 Exceptional (310) "Room and service were excellent." CA $233 CA $275 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Residence-Inn-By-Marriott-Middletown-Goshen.h48273068.Hotel-Information) ![1 bedroom, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/d940ee3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/b47258f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, body treatments, aromatherapy](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/6a5d9805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/2028d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wildflower Farms, Auberge Collection Gardiner 9.4/10 Exceptional (53) "Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect weekend getaway. Will definitely stay again, either with a group or just the 2 of us." CA $1,494 CA $1,733 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Gardiner-Hotels-Wildflower-Farms.h79873064.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/fda4e0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Canterbury, Luxury Queen, Fireplace](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/aeff4e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/6c09864d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/a124fb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cromwell Manor Inn Cornwall 9.4/10 Exceptional (85) "Very clean facility, very friendly innkeepers with excellent recommendations, excellent breakfast(made to order)" CA $323 CA $382 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/3b78b19a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/0a60ddfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/0230a235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33260000/33256300/33256205/d411dbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food CROTON HDSN 9.8/10 Exceptional (90) "Maria is a wonderful host. We enjoyed our stay. Thank you." CA $143 CA $361 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/White-Plains-Hotels-Luxury-2bd-Comfortstyle-45min-To-Nyc.h33256205.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=2025-10-28&endDate=2025-10-29®ionId=10021&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ![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 "Clean comfortable room. Bed was very comfortable. Hotel was quiet " [](https://expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The staff were extraordinary. From the moment we arrived to the moment we departed they were friendly, attentive to our needs and helpful with suggestions for a local restaurant that we could walk to (excellent Peruvian food!), to pouting out the freshly baked cookies and refreshed coffee and tea in the afternoon (we would have walked right past and the "pick me up" was just what we needed after a long day of travel. Claire, who works the evening shift, was especially helpful. Our room was clean and quiet although the bathroom was a bit dated. All in all we were delighted." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![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 "Great Views, very convenient " [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Homewood Suites Stewart Airport](//images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275_y.jpg) ### Homewood Suites Stewart Airport 10/10 Excellent "Clean and modern, friendly staff, great breakfast, and ev chargers worked!" [](https://expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![The Thayer Hotel at West Point](//images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Historic hotel with plenty of things to do" [](https://expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Inn on the Hudson](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47_y.jpg) ### Inn on the Hudson 10/10 Excellent "Convenient location. Friendly check in. " [](https://expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in New Windsor? > Are you and your partner looking for a romantic vacation? Our guests also enjoy New Windsor for its shopping, restaurants, and lakeside setting. If you'd like to explore some of the area's notable sights, you might make a stop by New Windsor Cantonment State Historic Site, Knox's Headquarters State Historic Site, or National Purple Heart Hall of Honor. If you'd like to stay close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list. ### When is the best time of year for a romantic getaway to New Windsor? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in New Windsor: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 32°F. The snowiest months in New Windsor are January, February, December, and March, with each month seeing an average of 6 inches of snowfall. ### What is there to do in New Windsor? > There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in New Windsor. Couples looking for a little of everything will enjoy New Windsor for its shopping, restaurants, and lakeside setting. You might think about stopping by New Windsor Cantonment State Historic Site, Knox's Headquarters State Historic Site, or National Purple Heart Hall of Honor while you're seeing the sights. ### What's the best way to get to New Windsor and around town during my romantic getaway? > This information about transportation options in New Windsor might help your romantic getaway go off without a hitch: The closest major airport is Stewart Intl. Airport (SWF), located 3.6 mi (5.8 km) from the city center. 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