Title: Book the Best Hotels with POOL in Wainscott Woods in 2026 | 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) ![If I could only "Trove" a smell. Delicious scones and brioches (cinnamon butter and chocolate chip options), etc.](https://images.trvl-media.com/place/6046784/0bf373aa-eedb-4229-8d1d-05cf084d6d0c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Miriam Marcus # Find Hotels with a Pool in Wainscott Woods, NY from CA $159 - ![](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 [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976471516&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![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) ![Dining](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/74678c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ceb2192e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, Charming, Lovely Farmhouse in Wainscott, East Hampton [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) Wainscott 10/10 Exceptional (112) "We had a great stay at the house - it's perfect for a family and the kids love the pool ! Would definitely stay again and perfect for long term rental as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy P. CA $992 CA $2,184 total includes taxes & fees Dec 16 - Dec 17 [](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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/a2d322f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/f417f407.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) ### Wainscott Woods Retreat [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information) Wainscott 7.0/10 Good (9) "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 $311 CA $355 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.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) ### Offshore Montauk [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) Montauk 9.4/10 Exceptional (79) "Nice decoration, clean amenities, good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) weihao CA $160 CA $261 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/4bbf34cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/1bfd9996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with cable channels, TV](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cbe6e5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (394) "great cost-effective option; room was very spacious and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isadora CA $163 CA $188 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.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 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 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) Southampton 8.6/10 Excellent (441) "Great weekend stay! staff was super kind and property was beautiful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chyanne CA $123 CA $159 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.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) ![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) ![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) ### Kenny's Tipperary Inn [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) Culloden Shores 8.4/10 Very good (878) "Really clean and nice location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiara [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.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 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) Montauk 9.2/10 Wonderful (1266) "Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Violet CA $191 CA $245 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/64ea9871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (546) "Awesome stay!!! Great Location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan CA $181 CA $274 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/abb4b75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/2fdf39bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/77f9f5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/17000000/16550000/16544700/16544673/72bc8ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hero Beach Club [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) Montauk 9.0/10 Wonderful (202) "Great weekend trip " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $197 CA $365 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Montauk-Hotels-Hero-Beach-Club.h16544673.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a3cd59ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/6f482e8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Queen Room](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/56176819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room with Balcony and Kitchen | Private kitchen](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/868b1d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daunt's Albatross Motel [](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information) Downtown Montauk 9.0/10 Wonderful (288) "The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany [](https://www.expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.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=2025-12-27&endDate=2025-12-28®ionId=553248635976471516&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Wainscott Woods Hotel Reviews ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg) ### Gurney's Montauk Resort & Seawater Spa 10/10 Excellent "EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay." [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Clean ,safety, nice staff." [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Great room with amazing views! Staff was fantastic and the food was great too" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Great hotel for a quick stay - very friendly staff" [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Bayview Resort](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "Just right. " [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![Sea Crest Resort](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Location. Staff. Space. " [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Beachcomber Resort at Montauk](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211971/d4cb08d2_y.jpg) ### Beachcomber Resort at Montauk 10/10 Excellent "Beautiful views and so close to town. Walk right down the driveway to the ocean! " [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![ Hampton's Vacation Inn](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77_y.jpg) ### Hampton's Vacation Inn 10/10 Excellent " didn't have a kitchen. parking was fine and convenient." [](https://expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Wainscott Woods? ### What is there to see and do in Wainscott Woods? ### When is the best time to book a hotel with a pool in Wainscott Woods? ## 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) - 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