Title: Book the Best Hotels with POOL in Wingdale in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/ccf149061fe165fab130b0cdc9acc5a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anna Arsenault # Find Hotels with a Pool in Wingdale, NY from CA $152 ![](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 Hotels with a Pool Tonight [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-18&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-19&endDate=2025-10-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wingdale Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/c70ad276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/409c2da8.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/bf263a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/79ae6795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG Danbury 9.0/10 Wonderful (244) "Clean room - great staff" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin CA $142 CA $163 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f224bafd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/3fa625b7.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) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection Southbury 8.4/10 Very good (1005) "Great stay!!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Geraldine CA $160 CA $203 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/e4abb59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/28ad5864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/f1893b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Poughkeepsie / Hudson Valley Crown Heights 8.8/10 Excellent (1016) "Great place to stay " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) sanyueh CA $149 CA $173 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/c695ef3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/130ec357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4ae12198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (351) "Great stay" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $160 CA $186 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/353de5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/eb2e5670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/2b43fa30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/b84054b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ethan Allen Hotel Danbury 7.8/10 Good (1033) "Great stay, very clean, beautiful hotel" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) JOHN CA $132 CA $152 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1011) "It was a great place to stay " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $150 CA $170 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/9bab7633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/42dbd033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/a76a124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/382d4dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Danbury-Bethel Danbury 8.6/10 Excellent (504) "Great stay. Nothing fancy but was great" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $136 CA $156 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/5883f255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/9adcfc3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/0368b452.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/35000000/34330000/34323400/34323334/9332f547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Poughkeepsie Poughkeepsie 9.6/10 Exceptional (985) "The staff made this a good stay" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy E CA $175 CA $204 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Poughkeepsie-Hotels-Homewood-Suites-By-Hilton-Poughkeepsie.h34323334.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/1f053b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/f4d4e3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/28b95632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/5476c121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Danbury Danbury 9.0/10 Wonderful (1012) "Amazing place" ![](https://a.travel-assets.com/egds/marks/flags/ca.svg) Patricia CA $171 CA $197 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Hampton-Inn-Danbury.h1445733.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/a5488d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/d2bf1069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Arcade](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/cb5c00ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/f35501d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Danbury Danbury 8.4/10 Very good (1016) "Great Hotel, quality price. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Eduardo CA $135 CA $155 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.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=2025-11-01&endDate=2025-11-02®ionId=553248635975862760&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Wingdale Hotel Reviews ![Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG](//images.trvl-media.com/lodging/1000000/700000/690800/690766/f70c64c6_y.jpg) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG 10/10 Excellent "Space was great" [](https://expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](//images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/4a7fc30b_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "Very nice set of rooms. Quite comfortable bed, the best we slept in all week. L shaped Sofa was great." [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.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) ![Quality Inn Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg) ### Quality Inn Poughkeepsie 10/10 Excellent "We were in the inside upstairs and tbe rooms are great!! Staff was amazing. They were redoing the parking lot so parking was limited but that wouldn't be a issue on going. " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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) ![Ethan Allen Hotel](//images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg) ### Ethan Allen Hotel 10/10 Excellent "Great stay, very clean, beautiful hotel" [](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](//images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 10/10 Excellent "Very enjoyable stay. The bed was comfortable. The pool and hot tub were great. The grounds were very well maintained and beautiful." [](https://expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Danbury](//images.trvl-media.com/lodging/1000000/20000/15100/15069/f35501d5_y.jpg) ### La Quinta Inn & Suites by Wyndham Danbury 10/10 Excellent "We were traveling with a rv and we were worried about parking and they had a huge area for trucks and campers. We were tired and they had a restaurant called Vans and it had a variety of food to choose from. They are pet friendly and we enjoyed the nice gentleman who took our reservation. " [](https://expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "This was a great stay for the money. Affordable and also safe, clean, and comfortable. Convenient parking. Wonderful staff. Would definitely stay again. " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Wingdale? > [Hampton Inn & Suites Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information): Provides daily, a seasonal outdoor pool, and free self parking. [Best Western Danbury/Bethel](https://www.expedia.ca/Danbury-Hotels-Best-Western-DanburyBethel.h4841.Hotel-Information): Offers a snack bar/deli, a seasonal outdoor pool, and free self parking. [Microtel Inn & Suites by Wyndham Bethel/Danbury](https://www.expedia.ca/Danbury-Hotels-Microtel-Inn-Suites-By-Wyndham-BethelDanbury.h579216.Hotel-Information): Hotel located near Vassar College. Provides buffet, an indoor pool, and free self parking. [Quality Inn & Suites Fishkill South near I-84](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Suites-Fishkill-South-Near-I-84.h1766609.Hotel-Information): Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. [Hotel Zero Degrees Danbury](https://www.expedia.ca/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information): Features a snack bar/deli, an indoor pool, and buffet. ### What is there to see and do in Wingdale? > Take a walk along the waterfront at Lake Waramaug State Park and Canopus Beach. Discover sights such as Dover Veterans Memorial Library, Harlem Valley Golf Club, and Leather Hill Preserve during your stay. ### When is the best time to book a hotel with a pool in Wingdale? > Taking into account the local weather in Wingdale is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 31°F. The snowiest months in Wingdale are January, February, March, and April, with each month seeing an average of 7 inches of snowfall. ## 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) - [Luxury Hotels in Carmel](https://www.expedia.ca/Carmel-Hotels-Luxury-Hotel.0-0-d553248634998943944-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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