Title: Book the Best BOUTIQUE Hotels in New Windsor in 2025 | 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 Boutique Hotels in New Windsor, NY from CA $155 ![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 New Windsor Boutique Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-01&endDate=2025-10-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-02&endDate=2025-10-03&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top New Windsor Boutique Hotels We don't have any properties that match your exact search [See all properties in New Windsor](https://expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17®ionId=10021&adults=2) ## Recommended hotels in New Windsor ![BBQ/picnic area](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/274a8ea0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/cefa7296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/747581be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Middletown - Goshen Middletown 8.4/10 Very good (1004) "great stay" CA $146 CA $173 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9.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/2000000/1790000/1789300/1789296/6459dee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/da52c924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/903ceccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury Central Valley 9.2/10 Wonderful (1002) "Great place to stay, very clean and conveniently located" CA $165 CA $203 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/b0cd51b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/fe678a50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/7e9b4daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Monroe - Woodbury Monroe 9.4/10 Exceptional (1000) "Great location." CA $158 CA $179 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![Blackout drapes, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/771d3275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d07e2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/d51e63c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1770000/1764800/1764709/945aae91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Stewart Airport New Windsor 9.2/10 Wonderful (1000) "We’ve stayed here once before and the service continues to be excellent. Breakfast buffet is great, staff is friendly and the rooms are clean and comfortable." CA $237 CA $268 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Newburgh-Hotels-Homewood-Suites-Stewart-Airport.h1764709.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/51570973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/1047d873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/6b6d035b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point New Windsor 8.4/10 Very good (1022) "Great price for a great hotel" CA $137 CA $155 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/309e00bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/09941fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/92dbf0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chester by IHG Chester 8.4/10 Very good (1000) "Everything was amazing! Thank You for a great stay. " CA $156 CA $184 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/30d2fd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/589f9bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windrose On Hudson Ossining 9.0/10 Wonderful (22) "The grounds were beautiful. The rooms were spacious and clean " CA $225 CA $250 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/53a095c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/c4928040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/5b25316b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1220000/1214400/1214332/c60ba6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Goshen Middletown Goshen 8.8/10 Excellent (1001) "Great place to stay when you’re in need of relaxation and some family time!" CA $141 CA $173 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Fairfield-Inn-Suites-By-Marriott-Goshen-Middletown.h1214332.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/59004f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/d8f79ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/1fb7d2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/9bf42dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express West Point by IHG Fort Montgomery 9.2/10 Wonderful (175) "Nice hotel in a nice area" CA $171 CA $194 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-West-Point.h860232.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58071d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/87e148ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/5d58f7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG Peekskill 9.2/10 Wonderful (1015) "Area and parking was safe and convenient. Staff were efficient and friendly. Breakfast was great as usual." CA $201 CA $230 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.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=2025-10-16&endDate=2025-10-17®ionId=10021&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top New Windsor Hotel Reviews ## Frequently asked questions ### What's there to see and do in New Windsor? > The shopping, restaurants, and lakeside setting are just some of the things to enjoy while you're in the area. Activities and attractions to experience around New Windsor include Woodbury Common Premium Outlets, Dia Beacon, and West Point Museum. You might also want to see places such as LEGOLAND® New York, United States Military Academy, and Paramount Hudson Valley Theater during your trip. ### What kind of weather should I plan for when I travel to New Windsor? > Having a good idea of the weather in New Windsor will help you enjoy your stay to the fullest. 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's the best way to get to my boutique hotel in New Windsor? > You have a few options for getting to and around New Windsor. The closest major airport is Stewart Intl. Airport (SWF), which is located 3.6 mi (5.8 km) from the heart of the city, but Danbury, CT (DXR-Danbury Municipal) may also be an option. 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