Title: New Windsor Cottages from CA $299 | 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 # Search New Windsor Cottage Rentals from CA $299 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=10021&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select New Windsor 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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/f9c1ab8a.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) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND Goshen 9.8/10 Exceptional (11) "Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - " CA $208 CA $410 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91400000/91391400/91391396/1c766ca2.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) ![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) ### Peaceful Cottage with Grill | Walk to Lake Putnam Valley 9.8/10 Exceptional (21) "Our second time staying at the cottage and we love it so much. So comfortable. So close to the lake, and just fabulous!" CA $255 CA $679 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Putnam-Valley-Hotels-Cottage-Getaway-DogFriendly.h91391396.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/70097ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4420f5da.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/84000000/83440000/83439100/83439008/5dd44347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks Kerhonkson 9.4/10 Exceptional (12) "Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. " CA $191 CA $356 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.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) ![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) ![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113159700/113159615/6a029a41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro Bloomingburg 10/10 Exceptional (1) "The place was as described, quaint, clean, no issues with communication or check in" CA $196 CA $299 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Bloomingburg-Hotels-Charming-Cottage-In-The-Lower-Catskills-Near-Ellenville-And-Wurtsboro.h113159615.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93190000/93185200/93185172/7863efed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93190000/93185200/93185172/2da613b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/94000000/93190000/93185200/93185172/6a61c4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93190000/93185200/93185172/4cd645f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Haven: A Romantic Retreat in our Tiny House! Middletown 7.0/10 Good (9) "we enjoyed the cozy home it is a nice place to get away" CA $210 CA $420 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Middletown-Hotels-Cozy-Haven-A-Romantic-Retreat-In-Our-Tiny-House.h93185172.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.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) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands Fort Montgomery 9.8/10 Exceptional (122) "It has an incredible mountain and water view. " CA $263 CA $431 total includes taxes & fees Oct 15 - Oct 16 [](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=2025-10-28&endDate=2025-10-29®ionId=10021&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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%2FNew-Windsor-Cottages.d10021-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FNew-Windsor-Cottages.d10021-aaCottages.Travel-Guide-Accommodation) ## Top New Windsor Hotel Reviews ![The Crossroads Hotel, Newburgh](//images.trvl-media.com/lodging/1000000/20000/14500/14410/5440914b_y.jpg) ### The Crossroads Hotel, Newburgh 10/10 Excellent "Yes " [](https://expedia.ca/Newburgh-Hotels-The-Crossroads-Hotel.h14410.Hotel-Information) ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "The stay was great. Front desk was super friendly. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](//images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "The parking garage needs a little more lighting at night. The ice machine on the 10th floor did not seem to be working so I ventured to the 8th floor for ice. Would be nice to have hook on the back of the bathroom door. liked that there was bottled water in my room." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Quality Inn & Suites Fishkill South near I-84](//images.trvl-media.com/lodging/2000000/1770000/1766700/1766609/12805cb0_y.jpg) ### Quality Inn & Suites Fishkill South near I-84 10/10 Excellent "Great " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.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 "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) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](//images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "I stay here whenever I’m in town and love this hotel excellent customer service nice clean and very comfortable!" [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Nice comfortably sized room" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](//images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "It felt like home.The staff was friendly.Parking was easy.Breakfast was great.This morning I will be staying there again" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ## Find out more about New Windsor ## New Windsor Cottages information | Number of reviews | 146 | | --- | --- | | Accommodation | 83 Cottages | | Lowest Price | CA $299 | | Highest Price | CA $679 | ## Frequently asked questions ### Why book your cottage in New Windsor with Expedia? > Reserving a cottage in New Windsor is as simple as clicking on your travel dates and picking an ideal place for outdoor fun and relaxation. From upmarket retreats to inexpensive properties and cottages that have amenities like laundry facilities, Expedia has something for all styles. As for epic deals? We've got them as well! ### How can I find cheap cottages in New Windsor? > The simplest way to find cheap cottages in New Windsor is with Expedia's user-friendly filter tool. Refine your search by amenities, budget and star rating to access awesome bargains with only a few clicks. ### What is there to do in New Windsor near my cottage? > If you want to discover the best of New Windsor, be sure to stop by [New Windsor Cantonment State Historic Site](https://www.expedia.ca/New-Windsor-Cantonment-State-Historic-Site-New-Windsor.d6171747.Vacation-Attraction). 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