Title: Top Chalets in Town of Crawford in 2026 | Expedia.ca [Town of Crawford Hotels](https://expedia.ca/Destinations-In-Town-Of-Crawford.d553248635976002380.Hotel-Destinations)[Vacation Rentals in Town of Crawford](https://expedia.ca/Destinations-In-Town-Of-Crawford.d553248635976002380.Vacation-Rental-Destinations)[Town of Crawford Car Rentals](https://expedia.ca/Destinations-In-Town-Of-Crawford.d553248635976002380.Car-Rental-Destinations)[Town of Crawford Vacations](https://expedia.ca/Town-Of-Crawford.d553248635976002380.Destination-Travel-Guides) ![Montgomery is a town in Orange County, New York, United States. The population was 22,606 at the 2010 census. It was named in honor of Richard Montgomery, an American Revolutionary War general killed in 1775 at the Battle of Quebec. The Town of Montgomery is in the northern part of the county at the county line shared by Ulster County. Montgomery is immediately west of the Town of Newburgh. It contains three villages, one also called Montgomery, as well as Walden and most of Maybrook.](https://images.trvl-media.com/place/8728/d5b50f96-b364-4937-ab55-555e72199f5b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ViajandoconAna Rustrian # Chalets in Town of Crawford ## Compare and save - ![](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 Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976002380&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976002380&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976002380&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976002380&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VILLA) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=VACATION_HOME) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Town+of+Crawford%2C+New+York%2C+United+States+of+America®ionId=553248635976002380&latLong=41.568542%2C-74.316829&adults=2&startDate=2026-03-17&d1=2026-03-17&endDate=2026-03-20&d2=2026-03-20&lodging=CHALET) ![](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%2FTown-Of-Crawford-Chalets.d553248635976002380-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FTown-Of-Crawford-Chalets.d553248635976002380-aaChalets.Travel-Guide-Accommodation) ## Top Town of Crawford Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Clean room. Clean lobby and public spaces " [](https://expedia.ca/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Clean room, nice amenities, great service, amazing staff" [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg) ### Sleep Inn & Suites Middletown - Goshen 10/10 Excellent "Very nice and cleab" [](https://expedia.ca/Newburgh-Hotels-Sleep-Inn-Suites-Middletown-Goshen.h16700177.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great location, friendly staff. Highly recommend " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point](https://images.trvl-media.com/lodging/1000000/880000/875700/875625/e8f6eb1b_y.jpg) ### Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point 10/10 Excellent "Love it, everytime we come this is the place to stay" [](https://expedia.ca/Newburgh-Hotels-Red-Roof-Inn-Suites-Newburgh-Stewart-Airport.h875625.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg) ### Holiday Inn Express Hotel & Suites Chester by IHG 10/10 Excellent "The breakfast was a hit, the place is clean and I would stay here again." [](https://expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Chester.h1194365.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 10/10 Excellent "Great Hotel A++" [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "For more than thirty years, every single time I have stayed at a Marriott Hotel, I have been massively impressed with the phenomenal level of customer service, cleanliness and comfortable rooms. Also, I LOVE seeing a lamp next to seating, so I can read a book and lounge, at the same time. Finally, I did not see any of donald trump's gestapo, which was a very good thing." [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Find out more about Town of Crawford ## Town of Crawford Chalets information | Number of reviews | 26 | | ----------------- | --------- | | Accommodation | 7 Chalets | | Lowest Price | CA $403 | | Highest Price | CA $1,352 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [2 Star Hotels in Walden ](https://www.expedia.ca/2Star-Walden-Hotels.s20-0-d6361117.Travel-Guide-Filter-Hotels) - [Hotels near Angry Orchard ](https://www.expedia.ca/Angry-Orchard-Hotels.0-l553248635998039554-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Cheap-Hotels.0-0-d3000448043-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bloomingburg ](https://www.expedia.ca/Bloomingburg-Hotels-Hotel-With-Pool.0-0-d3000448043-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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