Title: Book the Best Southampton WINERY Hotels in 2025 | Expedia.ca [Southampton Travel Guide](https://expedia.ca/Southampton.dx6782)[Hotels in Southampton](https://expedia.ca/Southampton-Hotels.d6782.Travel-Guide-Hotels)[Vacation Rentals in Southampton](https://expedia.ca/Southampton-Vacation-Rentals.d6782.Travel-Guide-VacationRentals)[Things to do in Southampton](https://expedia.ca/Things-To-Do-In-Southampton.d6782.Travel-Guide-Activities)[Southampton Car Rentals](https://expedia.ca/Car-Rentals-In-Southampton.d6782.Car-Rental-Guide)[Southampton Vacation Packages](https://expedia.ca/Southampton.d6782.Destination-Travel-Guides) ![Southampton](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252693-Southampton.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Southampton, NY from CA $201 ![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 Southampton Winery Hotels Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2025-10-09&endDate=2025-10-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6782&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southampton Winery Hotels ![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) ![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) ![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) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (350) "Return visitor. Great stay." CA $223 CA $255 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/ebb70869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/44648b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/f9e71e35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32210000/32202800/32202785/c4e80e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets! Southampton 9.0/10 Wonderful (10) "Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!" CA $1,811 CA $2,892 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Southampton-Hotels-Entire-House-In-Southampton-Village.h32202785.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5a99aefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, pillowtop beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5d4f757e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/3fa39065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Long Island-East End by IHG Riverhead 8.6/10 Excellent (1002) "Excellent facility and staff. Room was spacious and extremely clean. Look forward to staying here every trip to Long Island!" CA $205 CA $235 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (262) "Staff was amazing and this hotel is in the perfect location " CA $207 CA $237 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/4e100a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/6142ad8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/ae2cccbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton's Vacation Inn Hampton Bays 9.0/10 Wonderful (317) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." CA $176 CA $201 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ![Beach bar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/52eefc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio | View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/8f5285b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/65a8ebbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/c930d525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (133) "Beautiful beach all was great, loved breakfast At on site diner Nookies!" CA $364 CA $416 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/f1ad96fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/7abafcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (14) "Had a great stay here with a small group. Host was very accommodating and responsive. " CA $245 CA $608 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, free cabanas](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/eb1df3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5785cca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/934899a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayview Resort Hampton Bays 8.8/10 Excellent (447) "Staff was fantastic, room was always clean and the area was perfect! " CA $228 CA $260 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.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/f95ca887.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) ![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.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 6 - Nov 7 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![Suite, Balcony | View from room](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/48143ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/61dd3b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/c4314d53.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/10000000/9340000/9337100/9337066/84656cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean View Terrace Inn Hampton Bays 8.4/10 Very good (118) "This place was very nice and quiet. " [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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=2025-10-22&endDate=2025-10-23®ionId=6782&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southampton Hotel Reviews ![Capri](//images.trvl-media.com/lodging/8000000/7290000/7282200/7282139/ebd94379_y.jpg) ### Capri 10/10 Excellent "The Capri hotel is an awesome place to stay, it is fun, clean and is completely updated and so comfortable! The staff is super nice and helpful, and I would highly recommend it!! 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