Title: Book the Best Hamptons WINERY Hotels in 2026 | 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) ![Southampton](https://images.trvl-media.com/place/6782/a7d505fb-a998-4014-b234-d6dcbfce3eca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6782/a7d505fb-a998-4014-b234-d6dcbfce3eca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 18 - Mar 19](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-18&endDate=2026-03-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 19 - Mar 20](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-19&endDate=2026-03-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hamptons hotels with winery ![Reception](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2.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/54000000/53970000/53963000/53962986/88fef67d.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/d295eb3e.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) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (449 reviews) "Excellent place very relaxing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mireya CA $179 CA $206 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 lounge](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/6037fc82.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 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) Sag Harbor 9.4/10 Exceptional (585 reviews) "Lovely hotel, very clean and friendly! Definitely going back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hollie CA $281 CA $321 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information) ![Graybarn Cottage](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/dde88cf3.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](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/d1fe07eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Mill House Inn [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) Pantigo Road Historic District 9.0/10 Wonderful (81 reviews) "It is a very nice place, the staff is very friendly and the breakfast is very good. Also they have delicious teas, coffee, hot cider and snacks. We definitely recommend this hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eliane CA $342 CA $430 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/880e834f.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/10000000/9340000/9337100/9337066/2ef02017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/66365108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/f82468c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean View Terrace Inn [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.Hotel-Information) Hampton Bays 8.4/10 Very good (119 reviews) "This place was very nice and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly Ann [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/db3d6717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/9423d3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/88ff99e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Topping Rose House [](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) Bridgehampton 9.2/10 Wonderful (143 reviews) "Everything and everyone was just lovely! Comfortable Welcoming Great restaurant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachelle CA $733 CA $843 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ba8e29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/7bd037b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/ceb2192e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/2b5114d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private, Charming, Lovely Farmhouse in Wainscott, East Hampton [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) Wainscott 10/10 Exceptional (112 reviews) "Very clean rooms! Great place to stay! Great area and privacy! Host was wonderful. Would stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DAVID K. CA $493 CA $1,538 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) ![Beach nearby, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/028711b6.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) ![Property amenity](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/fa70e85b.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/a3bdf0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Roundtree, Amagansett [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) Amagansett North 10/10 Exceptional (94 reviews) "Thank you to the crew at The Roundtree for making our stay memorable! This is our second stay, so we couldn't turn down the evening smores by the fire and delivered warm cookies for a late night snack. The grounds and room were so beautiful. We will be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glenn CA $814 CA $976 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c88122e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/1e415396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/ef7e518d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c4935334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BlackBerry Private home with jacuzzi yearlong [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) East Hampton 9.0/10 Wonderful (4 reviews) "We had a great time staying here. The home is well worn and there are some fixtures that should be replaced " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne R. CA $142 CA $957 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75880000/75874300/75874275/66318f75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/76000000/75880000/75874300/75874275/bd5fe1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/76000000/75880000/75874300/75874275/8f2b0449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/76000000/75880000/75874300/75874275/977f0f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prime location, walk to all, cozy cottage Westhampton Beach [](https://www.expedia.ca/Westhampton-Beach-Hotels-Prime-Location.h75874275.Hotel-Information) Westhampton Beach CA $390 CA $774 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Westhampton-Beach-Hotels-Prime-Location.h75874275.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](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/fe6e5945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/2d824970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Beach Shack Studio](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/1c4953c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Sands Motel & Beach Bungalows [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) Greenport 9.8/10 Exceptional (148 reviews) "Everything was excellent, best hotel on the north fork. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.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=2026-04-02&endDate=2026-04-03®ionId=6056452&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Hamptons Hotel Reviews ![The Maidstone](https://images.trvl-media.com/lodging/10000000/9660000/9652100/9652095/d7688cb9_y.jpg) ### The Maidstone 10/10 Excellent "An absolute gem. Came for a quiet getaway and the perfect storm of calmness. Will is a wonderful host, making sure I was welll taken care of and focusing on every detail. He made sure I was able to check in and reach him during a winter storm and was readily available. The place is wonderful and filled with lots of fireplaces and room amenities that feel spa like and warm. Best night sleep I’ve had in a cloud of pillows and bed, in such a long time. Thank you so much for a wonderful time. " [](https://expedia.ca/East-Hampton-Hotels-The-Maidstone.h9652095.Hotel-Information) ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg) ### Topping Rose House 10/10 Excellent "Everything and everyone was just lovely! Comfortable Welcoming Great restaurant " [](https://expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) ## 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) - [Luxury Hotels in Bridgehampton ](https://www.expedia.ca/Bridgehampton-Hotels-Luxury-Hotel.0-0-d6130684-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Bridgehampton ](https://www.expedia.ca/Bridgehampton-Hotels-Pet-Friendly-Hotel.0-0-d6130684-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Bridgehampton ](https://www.expedia.ca/Bridgehampton-Hotels-Winery-Hotel.0-0-d6130684-tWineryHotel.Travel-Guide-Filter-Hotels) - 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