Title: Book the Best CHEAP Hotels in Wingdale, NY from CA $109 - Wingdale Cheap Hotels | 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 ![](https://images.trvl-media.com/place/553248635975862760/53b940fc-0a65-4ebe-8069-f8f2064c6482.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Wingdale Cheap Hotels Tonight [Feb 16 - Feb 17](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-02-16&endDate=2026-02-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Tomorrow [Feb 17 - Feb 18](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) This weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) ## Our top choices for Wingdale cheap hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/f9f5a554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/a207a569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/aae1f940.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Danbury/Bethel [](https://www.expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information) Bethel 7.8/10 Good (1,002 reviews) "Great stay thank you so much!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $97 CA $111 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/593124d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/0a1f1c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/49253eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) Southbury 8.4/10 Very good (1,009 reviews) "Very nice, staff were excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $161 CA $209 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/ecdcd2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/cefd2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (5) | Bathroom](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/3ff31723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/5fe2b5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Millerton Inn [](https://www.expedia.ca/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) Millerton 8.0/10 Very good (14 reviews) "Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $209 CA $237 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/11ffbd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/ec319ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/2c9da386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie [](https://www.expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) Highland 7.8/10 Good (962 reviews) "Super clean! Hotel manager along with all other employees were pleasant and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana CA $97 CA $109 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/7271a3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/bc5eecd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/d6a17faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/220000/216900/216870/75a6f271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus The Inn & Suites At The Falls [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) Red Oaks Mill 7.6/10 Good (444 reviews) "Nice and quaint hotel with beautiful creek behind surrounded by a dorest" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hiram CA $119 CA $134 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Poughkeepsie-Hotels-Best-Western-Plus-The-Inn-Suites-At-The-Falls.h216870.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/3879ce24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/c70440c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/42d801c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/436ff60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard By Marriott Danbury [](https://www.expedia.ca/Danbury-Hotels-Courtyard-By-Marriott-Danbury.h891471.Hotel-Information) Danbury 9.0/10 Wonderful (489 reviews) "Great location and super friendly and helpful staff. Everyone was wonderful and we had a nice stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Agata CA $151 CA $174 total includes taxes & fees Mar 13 - Mar 14 [](https://www.expedia.ca/Danbury-Hotels-Courtyard-By-Marriott-Danbury.h891471.Hotel-Information) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/579300/579216/eb555934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/579300/579216/ef4e0b3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/580000/579300/579216/ffcdbf0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/580000/579300/579216/becd7351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Bethel/Danbury [](https://www.expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information) Bethel 8.2/10 Very good (1,004 reviews) "Nice lit parking and easy check in clean and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $117 CA $135 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/b0b0d087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/ff2ecf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/020e6ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/d8605bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) Danbury 9.2/10 Wonderful (325 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $173 CA $199 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1206800/1206800/09571482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1210000/1206800/1206800/62e6efec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1210000/1206800/1206800/d8dbf763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/2000000/1210000/1206800/1206800/2c703962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Leaf Motel [](https://www.expedia.ca/Danbury-Hotels-Red-Carpet-Inn-Suites.h1206800.Hotel-Information) New Milford 5.6/10 (339 reviews) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allan [](https://www.expedia.ca/Danbury-Hotels-Red-Carpet-Inn-Suites.h1206800.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/30239db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/80e487b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/3a1a9879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/18a22a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Brewster [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information) Brewster 9.0/10 Wonderful (544 reviews) "Always great service and clean, comfy rooms. Breakfast is also decent every time, which isn’t always the case at hotels " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $172 CA $187 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.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=2026-03-03&endDate=2026-03-04®ionId=553248635975862760&adults=2&sort=BUDGET&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_553248635975862760) ## Top Wingdale Hotel Reviews ![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 10/10 Excellent "Staff nice. Good environment clean and comfortable " [](https://expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "The hotel staff was very welcome from as soon as you walked into the door. The room was very clean and comfortable. We really had a relaxing time " [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ![Extended Stay America Suites Fishkill Westage Center](https://images.trvl-media.com/lodging/1000000/1000000/994500/994440/c10c280b_y.jpg) ### Extended Stay America Suites Fishkill Westage Center 10/10 Excellent "Room was very lean" [](https://expedia.ca/Poughkeepsie-Hotels-Extended-Stay-America-Suites-Fishkill-Westage-Center.h994440.Hotel-Information) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "Room is awesome. Very large and comfortable " [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Ethan Allen Hotel](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg) ### Ethan Allen Hotel 10/10 Excellent "Hotel was nice. Love having a restaurant and bar on site especially since it was snowing" [](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.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 "Large, clean rooms. Easy parking. " [](https://expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.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 "Super nice staff! Very clean! Great breakfast and comfy beds! Go Hat" [](https://expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.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 "Room was very clean, safe and quiet hotel. Friendly and helpful staff" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ## Frequently asked questions ### How much does a budget hotel in Wingdale cost? ### Which area of Wingdale is best to stay in for cheap hotels? > Dover Plains, just a few miles south of Wingdale, offers some modest motel options that are generally more affordable than larger chain hotels. This quiet town provides a convenient base for exploring the surrounding Dutchess County. > > > Alternatively, Pawling, a slightly larger village to the west, also has a few independent inns and bed and breakfasts that might offer competitive rates. While not exclusively "cheap hotels", these options can sometimes provide better value than chain establishments in more developed areas. ### When is the most affordable time to visit Wingdale? > For solo travellers, the spring and autumn offer pleasant weather for exploring the natural beauty of the area, such as the numerous hiking trails and parks, which are free to access. The vibrant fall foliage is a particular draw, and while popular, visiting mid-week can help you avoid peak weekend prices. > > > Families might find winter to be surprisingly budget-friendly, especially if they enjoy outdoor activities like ice skating or snowshoeing, which can be done for free or at a low cost in various local spots. ### Is Wingdale a budget-friendly destination? > For accommodation, look for guesthouses or smaller inns outside the immediate town centre, or consider staying in nearby towns that offer lower rates, such as Pawling or Dover Plains, both easily accessible by car. Solo travellers might find more budget-friendly options in these surrounding areas, allowing them to commute into Wingdale for specific activities. > > > Couples can save on dining by packing picnics to enjoy at local parks or along the scenic Harlem Valley Rail Trail, which offers lovely views without a price tag. Many of Wingdale's attractions are nature-based and free, such as exploring the numerous walking paths and enjoying the picturesque rural landscape. ### How can I save on a budget hotel in Wingdale with Expedia? ### Is it cheaper to book flights and a hotel in Wingdale as a package? ### Can I cancel my budget hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Luxury Hotels in Amenia ](https://www.expedia.ca/Amenia-Hotels-Luxury-Hotel.0-0-d183634-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Amenia ](https://www.expedia.ca/Amenia-Hotels-Pet-Friendly-Hotel.0-0-d183634-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Carmel ](https://www.expedia.ca/Carmel-Hotels-Cheap-Hotels.0-0-d553248634998943944-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Carmel ](https://www.expedia.ca/Carmel-Hotels-Hotel-With-Pool.0-0-d553248634998943944-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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