Title: Book the Best Hotels with POOL in Sag Harbor in 2026 | Expedia.ca [Sag Harbor Travel Guide](https://expedia.ca/Sag-Harbor.dx154327)[Hotels in Sag Harbor](https://expedia.ca/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)[Vacation Rentals in Sag Harbor](https://expedia.ca/Sag-Harbor-Vacation-Rentals.d154327.Travel-Guide-VacationRentals)[Flights to Sag Harbor](https://expedia.ca/Cheap-Flights-To-Sag-Harbor.d154327.Travel-Guide-Flights)[Things to do in Sag Harbor](https://expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities)[Sag Harbor Car Rentals](https://expedia.ca/Car-Rentals-In-Sag-Harbor.d154327.Car-Rental-Guide)[Sag Harbor Vacation Packages](https://expedia.ca/Sag-Harbor.d154327.Destination-Travel-Guides) ![Sag Harbor](https://images.trvl-media.com/place/154327/a91ea3b6-915f-4999-ad18-23d61df0621a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Sag Harbor, NY from CA $166 - ![](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 Sag Harbor Hotels with a Pool Tonight [Jan 10 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=154327&startDate=2026-01-10&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 11 - Jan 12](https://www.expedia.ca/Hotel-Search?regionId=154327&startDate=2026-01-11&endDate=2026-01-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=154327&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=154327&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sag Harbor hotels with a pool ![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/e2b82008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/126bef9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/0ceaea9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5-bedroom house with water views and 2 houses from the bay. [](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) Sag Harbor CA $5,546 CA $8,863 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/d26d882e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/c1093eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/4c26b39e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/10a94b38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Water View w Dock 1.5ml from town [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information) Bay Point CA $6,239 CA $8,719 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/9b41c5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/0d06a5f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/bce72168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83270000/83267900/83267867/4fd6cfcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Room w use of pool/tennis in Spacious home [](https://www.expedia.ca/Sag-Harbor-Hotels-Large-Room-W-Use-Of-Pooltennis-In-Spacious-Home.h83267867.Hotel-Information) Sag Harbor CA $792 CA $1,122 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Sag-Harbor-Hotels-Large-Room-W-Use-Of-Pooltennis-In-Spacious-Home.h83267867.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 (882 reviews) "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) ![Pool](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/65c6d537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/4908c465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/ecf5693f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Indigo Long Island - East End by IHG [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) Riverhead 8.8/10 Excellent (1,001 reviews) "The places lovely good restaurant. Nice dinner excellent complimentary breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline CA $146 CA $166 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/56b46a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/003f8776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9b1283d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Long Island East End [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) Riverhead 9.2/10 Wonderful (1,001 reviews) "Clean and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $152 CA $173 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.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) ![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.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 (1,281 reviews) "Very beautiful place, staff are amazing. Thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $192 CA $247 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/83c7bce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Resort view](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (606 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $186 CA $252 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.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 (93 reviews) "Hotel was beautiful !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $145 CA $246 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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/44000000/43540000/43532300/43532300/717b3774.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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9.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 (561 reviews) "Everything was Great Immaculate hotel very good location sraff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) latoya CA $172 CA $236 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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=2026-01-24&endDate=2026-01-25®ionId=154327&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Sag Harbor Hotel Reviews ![Residence Inn by Marriott New York Long Island East End](https://images.trvl-media.com/lodging/19000000/18520000/18516100/18516036/b5361d70_y.jpg) ### Residence Inn by Marriott New York Long Island East End 10/10 Excellent "great place,I loved it" [](https://expedia.ca/Riverhead-Hotels-Residence-Inn-By-Marriott-New-York-Long-Island-East-End.h18516036.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) ![Hilton Garden Inn Riverhead](https://images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "Clean, well maintained stay with a working Gym " [](https://expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "Clean and quiet. " [](https://expedia.ca/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information) ![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg) ### Saybrook Point Resort & Marina 10/10 Excellent "All was beautiful" [](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![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 "Excellent " [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great place!" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Sea Crest Resort](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Lovely, clean 1 bedroom with spectacular view" [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.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) ## Frequently asked questions ### What are the best hotels in Sag Harbor with outdoor pools? > In addition to the pool, the Sag Harbor Inn offers complimentary continental breakfast, which is a great way to start the day without the hassle of dining out. Families appreciate the free WiFi and the availability of cribs at no extra charge, ensuring convenience during their stay. With a traveller review rating of 9.4, it's clear that visitors find the service to be fantastic and the location beautiful—a superb blend of comfort and accessibility. ### How much does a hotel with outdoor pool in Sag Harbor cost? ### Are there hotels with outdoor pools that are close to Havens Beach? > Families will appreciate the convenience of free continental breakfast and WiFi, along with complimentary toiletries and cribs for younger travellers. The self-parking option adds to the ease of your stay, making it a straightforward experience for those traveling with children. > > > In addition to the outdoor pool, the hotel's fantastic service and great coffee further enhance the family-friendly atmosphere, ensuring that your stay in Sag Harbor is both relaxing and enjoyable. ### Is it cheaper to book flights and a hotel in Sag Harbor as a package? ### How can I save on a hotel in Sag Harbor with Expedia? ### Can I cancel my hotel reservation on Expedia? ## 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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