Title: Book the Best Hotels with POOL in Lion Head Beach in 2025 | Expedia.ca [Lion Head Beach Travel Guide](https://expedia.ca/Lion-Head-Beach.dx553248635976395221)[Hotels in Lion Head Beach](https://expedia.ca/Lion-Head-Beach-Hotels.d553248635976395221.Travel-Guide-Hotels)[Vacation Rentals in Lion Head Beach](https://expedia.ca/Lion-Head-Beach-Vacation-Rentals.d553248635976395221.Travel-Guide-VacationRentals)[Lion Head Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Lion-Head-Beach.d553248635976395221.Car-Rental-Guide)[Lion Head Beach Vacation Packages](https://expedia.ca/Lion-Head-Beach.d553248635976395221.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Lion Head Beach, NY from CA $185 - ![](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 Lion Head Beach Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976395221&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Lion Head Beach Hotels with a Pool ![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) ![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) ![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 Greenport 8.8/10 Excellent (535) "Amazing property, rooms, and staff. Book a room with a balcony for amazing views!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $146 CA $236 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.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) ![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 Montauk 9.4/10 Exceptional (69) "Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $114 CA $210 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Montauk-Hotels-The-Offshore.h113578409.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 (1262) "Always excellent, even suring my eleventh stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl CA $194 CA $249 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.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 sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.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 lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamlet Inn Southampton 8.6/10 Excellent (437) "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 $143 CA $185 total includes taxes & fees Nov 21 - Nov 22 [](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) ![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) ![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 Culloden Shores 8.4/10 Very good (876) "Very clean and spacious room! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Beth CA $163 CA $193 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.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/16000000/15280000/15273200/15273178/43997189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport Greenport 8.6/10 Excellent (593) "Staff was amazing , room clean view phenomenal " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $224 CA $325 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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/ec2d268d.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 Southampton 9.6/10 Exceptional (382) "great cost-effective option; room was very spacious and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isadora CA $179 CA $206 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/58473cf5.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/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort Greenport 9.4/10 Exceptional (6) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin CA $273 CA $312 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/w2880h1079x0y0-f10fe240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Atlantic Hotel Southampton 7.2/10 Good (969) "Love the area love the room size clean parking was perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherwood [](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.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) ![Front of property](https://images.trvl-media.com/lodging/10000000/9510000/9501200/9501176/a4afa9ce.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 Downtown Montauk 9.0/10 Wonderful (283) "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=2025-12-04&endDate=2025-12-05®ionId=553248635976395221&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Lion Head Beach Hotel Reviews ![Hartmans' Briney Breezes Beach Resort](https://images.trvl-media.com/lodging/11000000/10650000/10646900/10646853/934c2137_y.jpg) ### Hartmans' Briney Breezes Beach Resort 10/10 Excellent "Love the views from our room. The room was very clean and the bed was super comfortable." [](https://expedia.ca/Montauk-Hotels-Hartmans-Briney-Breezes-Beach-Resort.h10646853.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Beautiful and unique property. We really enjoyed our weekend getaway " [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Cliffside Resort Condominiums](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg) ### Cliffside Resort Condominiums 10/10 Excellent "The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken. " [](https://expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.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 "Amazing experience." [](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.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) ![Hamlet Inn](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/15a14a38_y.jpg) ### Hamlet Inn 10/10 Excellent "Booked last minute and arrived late in the evening. Adorable property and room was cozy. Beds very comfortable. Will definitely return. Would have like to use the fire pit area but on limited time. Denise at the front desk was very accommodating and shared map along with beach tips to watch the sun come up. " [](https://expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information) ![Montauk Yacht Club](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f_y.jpg) ### Montauk Yacht Club 10/10 Excellent "Great hotel. Would like to come stay again in the summer." [](https://expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.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) ![The Atlantic Hotel](https://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) ## Frequently asked questions ### What are some accommodations with pools in Lion Head Beach? > [Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef's Kitchen](https://www.expedia.ca/East-Hampton-Hotels-Mid-Century-Holiday-Retreat-Private-Beach.h34146658.Hotel-Information): Features sun loungers, a 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): Offers 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): Provides 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): Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. [Sound View Greenport](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information): Features a private beach, a seasonal outdoor pool, and 2 bars. ### What is there to see and do in Lion Head Beach? > Spend some time experiencing the great outdoors at The Hamptons Beaches. During your stay, check out sights such as Pollock-Krasner House and Study Center, LongHouse Reserve, and Old Hook Mill. ### When is the best time to book a hotel with a pool in Lion Head Beach? > You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Lion Head Beach in the hottest months of August, July, or September when the average temperature 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 temperature is 38°F. ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Casino Hotels in Barnes Landing](https://www.expedia.ca/Barnes-Landing-East-Hampton-Hotels-Casino-Hotel.0-n553248635976472101-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Barnes Landing](https://www.expedia.ca/Barnes-Landing-East-Hampton-Hotels-Pet-Friendly-Hotel.0-n553248635976472101-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Barnes Landing](https://www.expedia.ca/Barnes-Landing-East-Hampton-Hotels-Spa-Hotel.0-n553248635976472101-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Business-Hotel.0-0-d177851-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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