Title: Book the Best Hotels with POOL in Wainscott in 2026 | Expedia.ca [Hotels in Wainscott](https://expedia.ca/Wainscott-Hotels.d6046784.Travel-Guide-Hotels)[Vacation Rentals in Wainscott](https://expedia.ca/Wainscott-Vacation-Rentals.d6046784.Travel-Guide-VacationRentals)[Wainscott Car Rentals](https://expedia.ca/Car-Rentals-In-Wainscott.d6046784.Car-Rental-Guide)[Wainscott Vacation Packages](https://expedia.ca/Wainscott.d6046784.Destination-Travel-Guides) ![Amerikanischer Strand auf Long Island bei New York](https://images.trvl-media.com/place/6046784/20a21c13-09f9-4231-8e0a-98fb1f8c34ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046784/20a21c13-09f9-4231-8e0a-98fb1f8c34ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Hotels with a Pool Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-02-06&endDate=2026-02-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-02-07&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Wainscott hotels with a pool ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/6a01643d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/5c1700b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) Wainscott 8.8/10 Excellent (223 reviews) - Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun. CA $198 CA $281 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ba8e29ea.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) ![Dining](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/74678c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/7bd037b9.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 reviews) CA $984 CA $2,157 total includes taxes & fees Feb 14 - Feb 15 [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/b309a772.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) ![Family Studio Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/e9280c9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, 1 King Bed](https://images.trvl-media.com/lodging/119000000/118540000/118532400/118532380/278d5c10.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 reviews) - Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats. CA $390 CA $446 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.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 (564 reviews) - Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation. CA $191 CA $258 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/7a155d22.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) ![El Presidente | View from room](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/0404b0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 2 Queens](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d.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 (100 reviews) CA $159 CA $259 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/85851742.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 (449 reviews) - Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island. CA $118 CA $153 total includes taxes & fees Feb 7 - Feb 8 [](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) ![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.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 (1,292 reviews) - Refreshing hilltop retreat with year-round pool access and sweeping ocean vistas. CA $189 CA $243 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/dc79a27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/89358591.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 (885 reviews) - Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces. [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/700cd038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/213ea8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![West Studio Queen and Full | Living area](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/fcfe3def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront 2BD Queen and 2 Twins | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/2b9ce1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windward Shores Ocean Resort [](https://www.expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) Napeague 8.8/10 Excellent (305 reviews) - Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts. CA $180 CA $236 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.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) ![1 bedroom, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/b432d22f.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/54000000/53970000/53963000/53962986/6222b412.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 (433 reviews) - Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation. CA $172 CA $198 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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=2026-02-20&endDate=2026-02-21®ionId=6046784&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Wainscott Breakfast included 4 stars Ocean view 5 stars Hot tub ## Top Wainscott 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 "Room was spotless, staff were great and the resort is top notch!!" [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![The Atlantic Hotel](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Clean hotel and conveniently located! " [](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information) ![Daunt's Albatross Motel](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a3cd59ff_y.jpg) ### Daunt's Albatross Motel 10/10 Excellent "Clean room, courteous staff and great location " [](https://expedia.ca/Montauk-Hotels-Daunts-Albatross-Motel.h9501176.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Amazing room and view from the room was perfect! " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Nice getaway spot in Southampton. Friendly staff. Well situated to may local points of interest. " [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Harborside Motel](https://images.trvl-media.com/lodging/20000000/19190000/19185200/19185143/cfcf412a_y.jpg) ### Harborside Motel 10/10 Excellent "Merle is the best" [](https://expedia.ca/Montauk-Hotels-Harborside-Motel.h19185143.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Wainscott? ### What is there to see and do in Wainscott? ### When is the best time to book a hotel with a pool in Wainscott? ## 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) - 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