Title: Book the Best Hotels with POOL in Wainscott Woods in 2025 | Expedia.ca [Wainscott Woods Travel Guide](https://expedia.ca/Wainscott-Woods.dx553248635976471516)[Hotels in Wainscott Woods](https://expedia.ca/Wainscott-Woods-Hotels.d553248635976471516.Travel-Guide-Hotels)[Vacation Rentals in Wainscott Woods](https://expedia.ca/Wainscott-Woods-Vacation-Rentals.d553248635976471516.Travel-Guide-VacationRentals)[Wainscott Woods Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott-Woods.d553248635976471516.Car-Rental-Guide)[Wainscott Woods Vacation Packages](https://expedia.ca/Wainscott-Woods.d553248635976471516.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/f54a09d2ea13aa6d589bee6eb9eaff7c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Miriam Marcus # Find Hotels with a Pool in Wainscott Woods, NY ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Wainscott Woods Hotels with a Pool Tonight [Sep 19 - Sep 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-09-19&endDate=2025-09-20&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 20 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-09-20&endDate=2025-09-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-09-19&endDate=2025-09-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wainscott Woods Hotels with a Pool ## Top Wainscott Woods Hotel Reviews ![Kenny's Tipperary Inn](//images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a_y.jpg) ### Kenny's Tipperary Inn 10/10 Excellent "Super friendly staff! Rooms and grounds were much nicer than I was expecting absolutely best value! " [](https://expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Clean and beautiful view" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Loved it" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Gurney's Montauk Resort & Seawater Spa](//images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Beachcomber Resort at Montauk](//images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Loved everything about the resort." [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "Having the the beach and a heated pool was terrific as was the room. It was definitley perfect for a quick get a way. Easy walking distances for places to eat. Chairs at the beach and lounges at the pool were comfortable and the staff was ery attentive. I have been going to Montauk for 30 or more years and this is a breath of fresh air compared to the other places that have yet to update. Will definitely be back." [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Ocean Vista Resort](//images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba_y.jpg) ### Ocean Vista Resort 10/10 Excellent "front desk staff / vibe / beach" [](https://expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![Ocean Surf Resort](//images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/7bd2ac6b_y.jpg) ### Ocean Surf Resort 10/10 Excellent "We loved everything" [](https://expedia.ca/Montauk-Hotels-Ocean-Surf-Resort.h12001193.Hotel-Information) ![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Thank you for such a wonderful vocation! We enjoyed our stay, and would go back there again." [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Wainscott Woods? > [Wainscott Woods Retreat](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information): Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. [Private, Charming, Lovely Farmhouse in Wainscott, East Hampton](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information): Offers sun loungers, a pool, and complimentary wireless internet access. [The Atlantic Hotel](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information): Provides 2 outdoor tennis courts, a seasonal outdoor pool, and continental. [Montauk Yacht Club](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information): Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's pool, and a private beach. [Sound View Greenport](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information): Offers a private beach, a seasonal outdoor pool, and 2 bars. ### What is there to see and do in Wainscott Woods? > Make a point to visit attractions like Georgica Beach and Railroad Museum of Long Island. During your stay, check out sights such as Wolffer Estates Vineyard, The Jewish Center of the Hamptons, and East Hampton Main Beach. ### When is the best time to book a hotel with a pool in Wainscott Woods? > You may want to consider an accommodation that offers an outdoor pool if you plan to visit Wainscott Woods in the hottest months of August, July, or September when the average temperature is 70°F. 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[Pet-Friendly Hotels in Village of East Hampton](https://www.expedia.ca/Village-Of-East-Hampton-Hotels-Pet-Friendly-Hotel.0-0-d553248634998945224-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Wainscott](https://www.expedia.ca/Wainscott-Hotels-Cheap-Hotels.0-0-d6046784-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Wainscott](https://www.expedia.ca/Wainscott-Hotels-Hotels-With-Kitchenettes.0-0-d6046784-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Spa Hotels in Wainscott](https://www.expedia.ca/Wainscott-Hotels-Spa-Hotel.0-0-d6046784-tSpaHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Boutique-Hotel.0-0-d6203488-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Cheap-Hotels.0-0-d6203488-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Family-Hotel.0-0-d6203488-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in West Side](https://www.expedia.ca/West-Side-Hotels-Hotels-With-Free-Breakfast.0-0-d6203488-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Luxury Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Luxury-Hotel.0-0-d6203488-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in West Side](https://www.expedia.ca/West-Side-Hotels-Winery-Hotel.0-0-d6203488-tWineryHotel.Travel-Guide-Filter-Hotels) - [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york) - [Book Hotels with a Pool in Wainscott Woods on Expedia.com](https://www.expedia.com/Wainscott-Woods-Hotels-Hotel-With-Pool.0-0-d553248635976471516-tHotelwithPool.Travel-Guide-Filter-Hotels)