Title: Book the Best Hamptons WINERY Hotels 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 Winery Hotels in Hamptons, NY ![](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 Hamptons Winery Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Hamptons Winery Hotels ![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.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) ![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.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) ### Sag Harbor Inn Sag Harbor 9.4/10 Exceptional (557) "Great place to stay!" CA $264 CA $302 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![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) ![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) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (354) "Really nice room, reasonably priced and very clean " CA $207 CA $237 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![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) ![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) ![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 (119) "This place was very nice and quiet. " CA $202 CA $315 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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) ![Panoramic Penthouse, 2 Queen Beds, Bay View | Living area](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/cd50a48f.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) ![Fishing](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/eb1df3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayview Resort Hampton Bays 8.8/10 Excellent (452) "Staff was fantastic, room was always clean and the area was perfect! " CA $229 CA $262 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.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) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.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) ![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (15) "Had a great stay here with a small group. Host was very accommodating and responsive. " CA $246 CA $615 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.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 (318) "A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street." CA $177 CA $202 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/e0e0def6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Room amenity](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1d639007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Graybarn Cottage | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1f2aee03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mill House Inn North Main Street Historic District 9.0/10 Wonderful (70) "Great experience at a wonderful property!" CA $457 CA $574 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/b8adcc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/1f4433ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/06408853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/c6fa26de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Roundtree, Amagansett Amagansett North 9.8/10 Exceptional (88) "The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. " CA $976 CA $1,171 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Single Beds | View from room](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9125969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/3f4839f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/d84c46bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Topping Rose House Bridgehampton 9.2/10 Wonderful (135) "Great rooms, staff and food" CA $1,132 CA $1,298 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/w1163h764x0y0-2c7bc0ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/8c3e97ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/36030f26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34005300/34005296/cfaa160d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches Water Mill 10/10 Exceptional (45) "Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. " CA $2,734 CA $4,805 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Water-Mill-Hotels-6-Bedroom-Bridgehampton-Estate.h34005296.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=2025-10-31&endDate=2025-11-01®ionId=6056452&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Hamptons Hotel Reviews ![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. 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