Title: Book the Best Amagansett WINERY Hotels in 2025 | Expedia.ca [Amagansett Travel Guide](https://expedia.ca/Amagansett.dx73561)[Hotels in Amagansett](https://expedia.ca/Amagansett-Hotels.d73561.Travel-Guide-Hotels)[Vacation Rentals in Amagansett](https://expedia.ca/Amagansett-Vacation-Rentals.d73561.Travel-Guide-VacationRentals)[Flights to Amagansett](https://expedia.ca/Cheap-Flights-To-Amagansett.d73561.Travel-Guide-Flights)[Amagansett Car Rentals](https://expedia.ca/Car-Rentals-In-Amagansett.d73561.Car-Rental-Guide)[Amagansett Vacation Packages](https://expedia.ca/Amagansett.d73561.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/ec859b78e239f6cc9a1827de2cb021dc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Amagansett, NY from CA $240 ![](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 Amagansett Winery Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=73561&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=73561&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=73561&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=73561&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Amagansett Winery Hotels ![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) ![Bicycling](https://images.trvl-media.com/lodging/11000000/10550000/10547800/10547745/65a49724.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) ![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 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 $832 CA $999 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.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) ![Exterior](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/0eb845c9.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 $314 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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) ![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/54000000/53970000/53963000/53962986/1bfd9996.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 $210 CA $240 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.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) ![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) ![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) ### 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 $614 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.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/d11f2952.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) ![Property entrance](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/db237a24.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 $263 CA $301 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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) ![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) ![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) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (136) "Great hotel and location. " CA $362 CA $414 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.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 $455 CA $572 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.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/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy quiet gem, private & fenced in backyard East Hampton 9.4/10 Exceptional (3) "good times" CA $139 CA $1,271 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/65eee158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c937e03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/51cab21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/1eb9ef8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town Greenport 10/10 Exceptional (1) "Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!" CA $378 CA $815 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.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) ![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 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) ### 6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches Water Mill 10/10 Exceptional (44) "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 $2,727 CA $4,792 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=2025-10-27&endDate=2025-10-28®ionId=73561&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Amagansett Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Amagansett North](https://www.expedia.ca/Amagansett-North-Amagansett-Hotels-Beach-Hotel.0-n553248635975748319-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Amagansett North](https://www.expedia.ca/Amagansett-North-Amagansett-Hotels-Hotels-With-Indoor-Pool.0-n553248635975748319-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Amagansett North](https://www.expedia.ca/Amagansett-North-Amagansett-Hotels-Luxury-Hotel.0-n553248635975748319-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Beach Hampton](https://www.expedia.ca/Beach-Hampton-Amagansett-Hotels-Adults-Only-Resorts.0-n553248635976481908-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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[Adults Only Resorts & in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Adults-Only-Resorts.0-0-d1524-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Beach-Hotel.0-0-d1524-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Boutique-Hotel.0-0-d1524-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Cheap-Hotels.0-0-d1524-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Family-Hotel.0-0-d1524-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Luxury-Hotel.0-0-d1524-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Oceanfront-Hotels.0-0-d1524-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Spa-Hotel.0-0-d1524-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Wedding-Hotels.0-0-d1524-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in East Hampton North](https://www.expedia.ca/East-Hampton-North-East-Hampton-Hotels-Adults-Only-Resorts.0-n553248634999126055-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in East Hampton North](https://www.expedia.ca/East-Hampton-North-East-Hampton-Hotels-All-Inclusive-Hotel.0-n553248634999126055-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in East Hampton North](https://www.expedia.ca/East-Hampton-North-East-Hampton-Hotels-Beach-Hotel.0-n553248634999126055-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in East Hampton North](https://www.expedia.ca/East-Hampton-North-East-Hampton-Hotels-Boutique-Hotel.0-n553248634999126055-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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