Title: Book the Best Hotels with POOL in Wainscott in 2025 | 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) ![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, NY from CA $187 - ![](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 [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-11-06&endDate=2025-11-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-11-07&endDate=2025-11-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6046784&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![Point of interest](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d13a2c2f.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 detail](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/9a89f493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sagaponack Wainscott 8.8/10 Excellent (198) "The room was spotless and had everything that you would need. Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie CA $237 CA $328 total includes taxes & fees Dec 7 - Dec 8 [](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/b65ad99d.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) ![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 Wainscott 10/10 Exceptional (112) "Gina was such a lovely host and ensured our stay was perfect. The house was spotless and had everything we needed. The property was very relaxing outside with a lovely warm pool. It was a lovely stay and in a great location. Thank you Gina." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Eileen M. CA $1,128 CA $2,380 total includes taxes & fees Nov 11 - Nov 12 [](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/119000000/118540000/118532400/118532380/280d0e8d.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) ### Wainscott Woods Retreat Wainscott 6.0/10 (7) "The room was utterly filthy. The bathroom had not been cleaned--the toilet was beyond dirty, there was no soap or lotion on the sink (I found the used bar soap on the shower floor), there was hair and dirt on the floor throughout the bathroom and bedroom. It was appalling. I was going to write a note before checking out, but there was no pen. The pool was filled with leaves. I would recommend others avoid this place at all costs. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill CA $311 CA $355 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.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) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98.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/ec2d268d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (368) "The staff was beyond helpful and nice, the rooms are huge and clean. Would definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ingrid CA $166 CA $190 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Ocean Front | Balcony view](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Blue Hotel Downtown Montauk 9.2/10 Wonderful (177) "Staff was nice beautiful news" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $163 CA $187 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.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/44000000/43540000/43532300/43532300/4e8534b4.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) ![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 Greenport 8.8/10 Excellent (526) "Beautiful view and room. Staff friendly and accommodating. Excellent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $181 CA $276 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/94835d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f43c4f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/2c93384d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e582d722.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort Greenport 10/10 Exceptional (1) "Great stay! Very clean and new. Comfy beds, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $275 CA $314 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.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) ![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) ![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 Montauk 9.4/10 Exceptional (65) "Beautiful views, quiet and clean. All around a great experience!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin CA $164 CA $348 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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) ![Front of property](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/efe89d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kenny's Tipperary Inn Culloden Shores 8.4/10 Very good (871) "Love this place. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan [](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) ![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.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) ![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 (1260) "Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lydia CA $195 CA $251 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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=2025-11-20&endDate=2025-11-21®ionId=6046784&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Wainscott Hotel Reviews ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "We love the Sound View. We stay every year for a girls’ weekend. Rooms are great with a beautiful view. One thing the rooms could use are a standing closet for your clothes. Otherwise, it’s lovely." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Montauk Yacht Club](//images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Loved the upgrade we received + the service all around as well!" [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg) ### Marram 10/10 Excellent "Wonderful stay! Spacious and elegant room, friendly staff, breathtaking view. Memorable birthday weekend. " [](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information) ![Kenny's Tipperary Inn](//images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/4e86636a_y.jpg) ### Kenny's Tipperary Inn 10/10 Excellent "Staff was nice " [](https://expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg) ### The Atlantic Hotel 10/10 Excellent "Perfect " [](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 "Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely" [](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 "It was a great room , it had everything we needed" [](https://expedia.ca/Montauk-Hotels-Beachcomber-At-Montauk.h2211971.Hotel-Information) ![ Hampton's Vacation Inn](//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) ![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) ## Frequently asked questions ### What are some accommodations with pools in Wainscott? > [The Sagaponack](https://www.expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information): B&B located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. [Wainscott Woods Retreat](https://www.expedia.ca/Wainscott-Hotels-Wainscott-Woods-Retreat.h118532380.Hotel-Information): Hotel located near The Hamptons Beaches. Offers 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. Provides 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. Features sun loungers, an indoor pool, and complimentary wireless internet access. [The Atlantic Hotel](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information): Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. ### What is there to see and do in Wainscott? > The picturesque setting of The Hamptons Beaches showcases the area's natural beauty. Discover sights such as Georgica Beach, Wolffer Estates Vineyard, and East Hampton Main Beach during your stay. Take in the natural beauty of Wainscott with the beaches. ### When is the best time to book a hotel with a pool in Wainscott? > You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Wainscott in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp 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) - 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