Title: Wingdale Guest Houses from CA $269 | Expedia.ca [Hotels in Wingdale](https://expedia.ca/Wingdale-Hotels.d553248635975862760.Travel-Guide-Hotels)[Vacation Rentals in Wingdale](https://expedia.ca/Wingdale-Vacation-Rentals.d553248635975862760.Travel-Guide-VacationRentals)[Wingdale Car Rentals](https://expedia.ca/Car-Rentals-In-Wingdale.d553248635975862760.Car-Rental-Guide)[Wingdale Vacation Packages](https://expedia.ca/Wingdale.d553248635975862760.Destination-Travel-Guides) ![Thought this reflection in the abandoned Olivet University in Wingdale, NY was pretty cool. The inside of the building were overgrown with all kinds of plants and the way the tree behind me reflected in the glass made it harder to tell what was inside and what was out. #culture #culturephotocontest](https://images.trvl-media.com/place/553248635975862760/53b940fc-0a65-4ebe-8069-f8f2064c6482.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anna Arsenault # Search Guest Houses in Wingdale from CA $269 - ![](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 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Wingdale Guest Houses ![Deluxe Apartment | Living area](https://images.trvl-media.com/lodging/21000000/20160000/20155900/20155827/b2f9fdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment | Living area](https://images.trvl-media.com/lodging/21000000/20160000/20155900/20155827/5e918972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment | Private kitchen](https://images.trvl-media.com/lodging/21000000/20160000/20155900/20155827/c2a856d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/21000000/20160000/20155900/20155827/faf4467b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station Inn Pawling Pawling 9.0/10 Wonderful (185) "Very nice setup. Easy to Book and check in. I will stay there again on my next trip to that area. Thank you-JM" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james CA $237 CA $269 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Station-Inn-Pawling.h20155827.Hotel-Information) ![The Parlor Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b4671c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/7bbc5c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite | Private kitchen](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/b8c74868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Loft Suite | In-room dining](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/w5552h4162x0y0-c20c0fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9 Academy Salisbury 9.0/10 Wonderful (10) "Nice room. " ![South Korea](https://a.travel-assets.com/egds/marks/flags/kr.svg) JeongHoon CA $682 CA $785 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2025-12-22&endDate=2025-12-23®ionId=553248635975862760&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&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%2FWingdale-Guest-Houses.d553248635975862760-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWingdale-Guest-Houses.d553248635975862760-aaGuestHouses.Travel-Guide-Accommodation) ## Top Wingdale Hotel Reviews ![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg) ### Hyatt Place Poughkeepsie / Hudson Valley 10/10 Excellent "great amenities, staff was super helpful. Clean room" [](https://expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Danbury](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/f35501d5_y.jpg) ### La Quinta Inn & Suites by Wyndham Danbury 10/10 Excellent "Staff was very helpful." [](https://expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) ![Homewood Suites by Hilton Poughkeepsie](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/0368b452_y.jpg) ### Homewood Suites by Hilton Poughkeepsie 10/10 Excellent "Everything just right" [](https://expedia.ca/Poughkeepsie-Hotels-Homewood-Suites-By-Hilton-Poughkeepsie.h34323334.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 "Staff was very courteous; bathtub had some dirt or smudge spots so I wiped it down but I can be particularl. Overall, a very positive experience. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Comfort Inn & Suites Danbury-Bethel](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/42dbd033_y.jpg) ### Comfort Inn & Suites Danbury-Bethel 10/10 Excellent "Clean room,staff we great" [](https://expedia.ca/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.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 "It was very comfortable and the staff was polite and helpful." [](https://expedia.ca/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "Was clean, Clerk very pleasant and friendly." [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![Best Western Danbury/Bethel](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc_y.jpg) ### Best Western Danbury/Bethel 10/10 Excellent "clean room, quick checkin, good breakfast, very good location" [](https://expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/w4000h2662x0y0-e2ffacae_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Beautiful Inn with a spacious and lovely room." [](https://expedia.ca/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ## Find out more about Wingdale ## Wingdale Guest Houses information | Number of reviews | 194 | | ----------------- | -------------- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $269 | | Highest Price | CA $785 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Millbrook ](https://www.expedia.ca/5Star-Millbrook-Hotels.s50-0-d6051715.Travel-Guide-Filter-Hotels) - [B&B in Amenia ](https://www.expedia.ca/Amenia-Bed-And-Breakfast.d183634-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Inns in Amenia ](https://www.expedia.ca/Amenia-Inns.d183634-aaInns.Travel-Guide-Accommodation) - [Resorts in Amenia ](https://www.expedia.ca/Amenia-Resort-Hotels.d183634-aaResortHotels.Travel-Guide-Accommodation) - [Chalets in Appalachian Trail ](https://www.expedia.ca/Appalachian-Trail-Chalets.d553248635947269058-aaChalets.Travel-Guide-Accommodation) - 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