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 15 - Mar 16](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-15&endDate=2026-03-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 16 - Mar 17](https://www.expedia.ca/Hotel-Search?regionId=6056452&startDate=2026-03-16&endDate=2026-03-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) In two weeks [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) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/c5b3ea42.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) ### The Bentley Hotel Southampton [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) Southampton 9.6/10 Exceptional (446 reviews) "Rooms were very well kept and the design was unique!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan CA $180 CA $207 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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/5688a130.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) ![Outdoor pool](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/14a9b9bf.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 (584 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 16 - Mar 17 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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) ![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) ![Outdoor wedding area](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/9c174ca3.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) ### 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 CA $146 CA $242 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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) ![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](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/d1fe07eb.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 $343 CA $431 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.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) ![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) ### Topping Rose House [](https://www.expedia.ca/Bridgehampton-Hotels-Topping-Rose-House.h5581380.Hotel-Information) Bridgehampton 9.2/10 Wonderful (143 reviews) "Great rooms, staff and food" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Alexandra CA $735 CA $844 total includes taxes & fees Mar 16 - Mar 17 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/33000000/32400000/32391300/32391262/7bd037b9.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 $494 CA $1,541 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Wainscott-Hotels-Private.h32391262.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/9304004e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/305503f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/e51e1447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/6f587bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Immaculate Waterfront 2 bedroom! [](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information) Hampton Bays 10/10 Exceptional (5 reviews) "Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael L. CA $446 CA $882 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.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/a3bdf0f5.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/11000000/10550000/10547800/10547745/06408853.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 (93 reviews) "Fantastic hotel, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tunca CA $815 CA $978 total includes taxes & fees Mar 16 - Mar 17 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/9825549c.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 $181 CA $1,008 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/9626c6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/0a29c96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/91eb12d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/830deaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Hampton Estate for 8, Sauna, Soaking Tub, Chef\`s Kitchen, Outdoor Fireplace [](https://www.expedia.ca/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information) East Hampton North CA $367 CA $1,115 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.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=2026-03-29&endDate=2026-03-30®ionId=6056452&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_6056452) ## 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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