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 $141 ![](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 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-10-27&endDate=2025-10-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [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) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975862760&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wingdale Hotels with a Pool ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.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) ![Property entrance](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f44c391a.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 (1004) "Great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geraldine CA $160 CA $203 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/c70ad276.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) ![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/ff2ecf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG Danbury 9.2/10 Wonderful (250) "Clean, comfortable good breakfast..great coffee" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $144 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/382d4dcb.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/1000000/20000/16500/16474/84d5ee46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Danbury-Bethel Danbury 8.4/10 Very good (515) "Great stay. Nothing fancy but was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $142 CA $163 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.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) ![Daily full breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0.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 (1044) "Great stay, very clean, beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOHN CA $126 CA $145 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.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) ![Lobby](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4ae12198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4eb66254.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) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (361) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $160 CA $185 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.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) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/c1f101cf.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) ![Exterior](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Poughkeepsie / Hudson Valley Crown Heights 8.8/10 Excellent (1005) "we stayed 2 nights midweek, very comfortable, quiet and everything was top notch!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) GARY CA $165 CA $192 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/239951b5.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) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1017) "It was a great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $150 CA $169 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/1000000/20000/15100/15069/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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/f35501d5.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) ### La Quinta Inn & Suites by Wyndham Danbury Danbury 8.4/10 Very good (1003) "Great Hotel, quality price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eduardo CA $133 CA $153 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/9bb5ee16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/3070b4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/be375701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Poughkeepsie Arlington 7.8/10 Good (461) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $121 CA $141 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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/2000000/1450000/1445800/1445733/28b95632.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/f4d4e3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Danbury Danbury 9.0/10 Wonderful (1005) "Large rooms with plenty of free outside parking. Breakfast spread was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clare CA $171 CA $197 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Hampton-Inn-Danbury.h1445733.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=2025-11-09&endDate=2025-11-10®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 "Clean Room Staff was welcoming" [](https://expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Ethan Allen Hotel](//images.trvl-media.com/lodging/1000000/850000/848400/848360/9fd70ba0_y.jpg) ### Ethan Allen Hotel 10/10 Excellent "Front desk was extremely helpful and went above and beyond to help with any requests. " [](https://expedia.ca/Danbury-Hotels-Ethan-Allen-Hotel.h848360.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 "Hampton inn newly refurbished " [](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 "x" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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 "Ok" [](https://expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.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 "All of the employees that we met were very kind, courteous, professional, and willing to help" [](https://expedia.ca/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.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 "Good breakfast with lits if choices. Quiet lication with ample free parking." [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Courtyard by Marriott Fishkill](//images.trvl-media.com/lodging/1000000/20000/17300/17286/3f9cb655_y.jpg) ### Courtyard by Marriott Fishkill 10/10 Excellent "Very good customer service. Staff handles issues very well!" [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Fishkill.h17286.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 "Very clean, nice and convenient to get from car to room. My husband said they had the best shower water pressure he had ever experienced in his entire life. Lol. Awesome stay! Very quiet when we were there. " [](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): Hotel, 7-minute walk from Vassar College. Provides daily, an indoor 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): Features daily, a seasonal outdoor pool, and free self parking. [Quality Inn Poughkeepsie](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information): Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. [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 a snack bar/deli, a seasonal outdoor pool, and free self parking. [Hotel Zero Degrees Danbury](https://www.expedia.ca/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information): Hotel located near Vassar College. Features buffet, an indoor pool, and free self parking. ### 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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