Title: Book the Best Hotels with POOL in Hamptons in 2025 | Expedia.ca [Hamptons Travel Guide](https://expedia.ca/Hamptons.dx6056452)[Hotels in Hamptons](https://expedia.ca/Hamptons-Hotels.d6056452.Travel-Guide-Hotels)[Vacation Rentals in Hamptons](https://expedia.ca/Hamptons-Vacation-Rentals.d6056452.Travel-Guide-VacationRentals)[Flights to Hamptons](https://expedia.ca/Cheap-Flights-To-Hamptons.d6056452.Travel-Guide-Flights)[Things to do in Hamptons](https://expedia.ca/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities)[Hamptons Car Rentals](https://expedia.ca/Car-Rentals-In-Hamptons.d6056452.Car-Rental-Guide)[Hamptons Vacation Packages](https://expedia.ca/Hamptons.d6056452.Destination-Travel-Guides) ![Shadmoor State Park showing a sandy beach and general coastal views as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252390-Montauk.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Hamptons, NY ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Hamptons Hotels with a Pool Tonight [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Hamptons Hotels with a Pool ![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) ![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) ![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) ### Montauk Manor Montauk 9.2/10 Wonderful (1252) "Beautiful grounds, excellent staff" CA $176 CA $228 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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) ![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 Montauk 9.2/10 Wonderful (56) "The staff is excellent and very accommodating. Great place in a great location. Would stay here again." CA $206 CA $395 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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) ![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) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/c7873724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/5c314659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Montauk Yacht Club Montauk 8.6/10 Excellent (1001) "Wonderful hotel and location " CA $271 CA $469 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/d11f2952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/f95ca887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/db237a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Inn Sag Harbor 9.4/10 Exceptional (557) "Great place to stay!" CA $262 CA $300 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/aa9cc8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/6d8b086b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/9bf97ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Cottage](https://images.trvl-media.com/lodging/84000000/83520000/83519500/83519458/5c9db42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canoe Place Inn and Cottages Hampton Bays 9.8/10 Exceptional (58) "Amazing property. Really enjoyed our stay." CA $573 CA $695 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hampton-Bays-Hotels-Canoe-Place-Inn-And-Cottages.h83519458.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/e6b2036b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/14ba9bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/59e33701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207142/d8406ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Resort Montauk 9.0/10 Wonderful (235) "Great place to stay for small family " CA $201 CA $275 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Montauk-Hotels-Driftwood-Resort.h4207142.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) ![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) ![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 Montauk 9.2/10 Wonderful (149) "It is aperfect no-frills hotel right on the beach at an extremely reasonable price, walkable to great dining, shopping and more" CA $204 CA $234 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information) ![Street view](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/abad495f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/8593ea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/67609737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12010000/12001200/12001193/a0998934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Surf Resort Montauk 8.4/10 Very good (210) "The view from our balcony was beautiful! We watched whales and dolphins swim by. Hotel is close to restaurants and town and very walkable. Would definitely stay again " CA $170 CA $195 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Montauk-Hotels-Ocean-Surf-Resort.h12001193.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/7d31a3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/03887d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/51a7b673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, free beach shuttle, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/120000/117200/117135/05958fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southampton Inn Southampton 8.6/10 Excellent (539) "Close to everything!! " CA $279 CA $342 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Southampton-Inn.h117135.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/ab3c0766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/6bc86eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/e2b4ce6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed (Upper Level)](https://images.trvl-media.com/lodging/10000000/9630000/9622400/9622352/19012da7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Resort Inn Montauk 9.6/10 Exceptional (473) "Great Staff , the pool and property was spotless , great views!." CA $152 CA $196 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Montauk-Hotels-Ocean-Resort-Inn.h9622352.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=2025-10-19&endDate=2025-10-20®ionId=6056452&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Hamptons Hotel Reviews ![Bayview Resort](//images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg) ### Bayview Resort 10/10 Excellent "Drinks on the pier were lovely!" [](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information) ![Baron's Cove](//images.trvl-media.com/lodging/2000000/1150000/1148900/1148848/560aa55e_y.jpg) ### Baron's Cove 10/10 Excellent "Parking was free and really easy. Great proximity to the main street of town—you can easily walk, but it's not too close where it gets loud at night. The front staff and cleaning team were all lovely and super helpful. We loved the coffee bar in the mornings. " [](https://expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![Windward Shores Ocean Resort](//images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/23c43d21_y.jpg) ### Windward Shores Ocean Resort 10/10 Excellent "The non ocean view rooms are fabulous. I’m sure the ocean side ones are great. " [](https://expedia.ca/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information) ![Sea Crest Resort](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769_y.jpg) ### Sea Crest Resort 10/10 Excellent "Perfect location!" [](https://expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information) ![Hamlet Inn](//images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Property set gorgeous staff incredibly helpful polite professional " [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Ocean Vista Resort](//images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba_y.jpg) ### Ocean Vista Resort 10/10 Excellent "Lovely short stay! Right on the beautiful beach. Staff were so welcoming and even quickly sent me something I accidentally left behind in the room. Absolutely plan to be back!" [](https://expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information) ![Southampton Inn](//images.trvl-media.com/lodging/1000000/120000/117200/117135/7d31a3c7_y.jpg) ### Southampton Inn 10/10 Excellent "Clean room" [](https://expedia.ca/Southampton-Hotels-Southampton-Inn.h117135.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 "OK. I don't typically write effusive reviews...or write many online ratings. When I do, it's because the service or product is exceptional (and in rare cases, abysmal). I was born and lived in the "Hamptons" as a boy and a teenager. I returned to show my family where I grew up. I last visited the area 35 years ago in this rare and beautiful place on the South Fork of Long Island. A flood of boyhood memories were augmented and complemented by the Hampton's Vacation Inn. Dayan made everything easy and seamless because she was personally responsive. The easily accessible and convenient property and cottages provide a quiet pastoral environment within the activity that is "The Hamptons" with Stop & Shop literally across Montauk Highway (though we couldn't tell the 2-lane "highway" was just yards away) and Classic Beverage adjacent. Multiple dining and shopping options are readily available and within easy walking distance. We recommend Dero's supervised by Air Force veteran Paul who is the patriarch of the family restaurant business. Our 2 BR quiet cottage was clean, comfy, cozy, welcoming and well-equipped. Hampton's Vacation Inn quietly demands that you power down, relax and enjoy this magical place." [](https://expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ![The Hampton Maid](//images.trvl-media.com/lodging/20000000/19720000/19716000/19715959/e820e996_y.jpg) ### The Hampton Maid 10/10 Excellent "I love it!" 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