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 from CA $190 ![](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 Wainscott Woods Hotels with a Pool Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&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=553248635976471516&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wainscott Woods Hotels with a Pool ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/b65ad99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/9c4e1f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/74678c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/6e9b06d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, Charming, Lovely Farmhouse in Wainscott, East Hampton Wainscott 10/10 Exceptional (112) "Loved our return stay to this beautiful property and home. Everything is in great condition. Pristine and clean. Great location. Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robyn S. CA $1,119 CA $2,373 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/61e9bea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/d97fb6c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/280d0e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/1c35aedc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wainscott Woods Retreat Wainscott 6.8/10 (6) "Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivan CA $293 CA $335 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information) ![Indoor pool, open 10:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/bd8b651c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium King Ocean Front](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/720dfd39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/d8d28e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (170) "The beach view is spectacular the surrounding area has everything you need for a each getaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $167 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/8fa06225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn Culloden Shores 8.4/10 Very good (869) "Love this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $162 CA $193 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, beach towels](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8a104c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn Southampton 8.6/10 Excellent (432) "A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $150 CA $194 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Manor Montauk 9.2/10 Wonderful (1257) "Beautiful grounds, excellent staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jess CA $212 CA $269 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1005) "Wonderful hotel and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FIONA CA $222 CA $414 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Indoor pool, a waterfall pool](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/85e54318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/20fb5209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/98ce732d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Vista Resort Amagansett 9.0/10 Wonderful (198) "Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kayla c CA $188 CA $214 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Offshore Montauk Montauk 9.4/10 Exceptional (63) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $209 CA $399 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/e408e278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 3 Bedrooms, 2 Bathrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/4119983f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/0c1795de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Crest Resort Amagansett 9.2/10 Wonderful (498) "Perfect location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bernadette CA $240 CA $305 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.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=2025-11-08&endDate=2025-11-09®ionId=553248635976471516&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Wainscott Woods Hotel Reviews ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Breakfast and the Halyard restaurant are top shelf. A few quirks with our room(s) - no cable service, a locked bathroom door that couldn’t be opened, and a dead bolt that didn’t work- but the staff were helpful and accommodating and did everything they could to make things right." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Hero Beach Club](//images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/77f9f5ea_y.jpg) ### Hero Beach Club 10/10 Excellent "We liked the location and the staff was very accommodating with our schedule." [](https://expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) ![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Amazing view. Rooms were clean and provided enough space " [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.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 "Extremely clean, very quiet with a beautiful view of the ocean, great kitchen, highly recommend " [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great stay overall. Only suggestion would be to put a light on the side of the building. " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful. " [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Sun N Sound](//images.trvl-media.com/lodging/5000000/4230000/4225500/4225489/5de1d3d0_y.jpg) ### Sun N Sound 10/10 Excellent "Grear" [](https://expedia.ca/Montauk-Hotels-Sun-N-Sound.h4225489.Hotel-Information) ![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Staffs were so kind. The place was peaceful and it is really a relaxing place to stay especially it is beach front" [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.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 "wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities" [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.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. [Gurney's Montauk Resort & Seawater Spa](https://www.expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information): Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. [Montauk Blue Hotel](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information): Hotel, 1-minute walk from The Hamptons Beaches. Provides sun loungers, an indoor pool, and complimentary wireless internet access. [Marram](https://www.expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information): Hotel, 6-minute walk from The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and sun loungers. [Sound View Greenport](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information): Features 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. Lodging with an indoor pool may be what you want if you visit during the coldest months of January, February, or March when the average temperature is 38°F. ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Beach-Hotel.0-0-d6130684-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Boutique-Hotel.0-0-d6130684-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Cheap-Hotels.0-0-d6130684-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Luxury-Hotel.0-0-d6130684-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Pet-Friendly-Hotel.0-0-d6130684-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Bridgehampton](https://www.expedia.ca/Bridgehampton-Hotels-Winery-Hotel.0-0-d6130684-tWineryHotel.Travel-Guide-Filter-Hotels) - 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