Title: Book the Best North Main Street Historic District WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in East Hampton](https://expedia.ca/East-Hampton-Vacation-Rentals.d1524.Travel-Guide-VacationRentals)[Flights to East Hampton](https://expedia.ca/Cheap-Flights-To-East-Hampton.d1524.Travel-Guide-Flights)[Things to do in East Hampton](https://expedia.ca/Things-To-Do-In-East-Hampton.d1524.Travel-Guide-Activities)[North Main Street Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-North-Main-Street-Historic-District.d553248621557934296.Car-Rental-Guide)[North Main Street Historic District Vacations](https://expedia.ca/North-Main-Street-Historic-District.d553248621557934296.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252638-East-Hampton.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in North Main Street Historic District, 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 North Main Street Historic District Winery Hotels Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=553248621557934296&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248621557934296&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621557934296&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621557934296&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top North Main Street Historic District Winery Hotels ![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 | 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) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/f6e6bd4f.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $456 CA $573 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/East-Hampton-Hotels-Mill-House-Inn.h2861838.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) ![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) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (359) "Really nice room, reasonably priced and very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joanna CA $210 CA $240 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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 (119) "This place was very nice and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly Ann CA $202 CA $314 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New and Modern Bridgehampton Accommodations Bridgehampton 9.6/10 Exceptional (15) "Great home, as pictured, perfect place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter R. CA $246 CA $613 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Property entrance](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/db237a24.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) ### Sag Harbor Inn Sag Harbor 9.4/10 Exceptional (559) "Staff was extremely friendly. Continental breakfast with great options. Location was walkable to downtown area. Will definitely stay here the next time I visit Sag Harbor. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Quinton CA $264 CA $301 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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) ![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/11000000/10550000/10547800/10547745/06408853.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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina CA $974 CA $1,169 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Amagansett-Hotels-The-Roundtree.h10547745.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) ![Exterior](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/780134b3.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](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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyn CA $410 CA $469 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/aed266db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.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) "Perfect stay outside of the hustle and bustle of Manhattan. The house offered just what we needed a refugee from the city. With plenty of comfortable rooms for the six of us." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shakirah S. CA $175 CA $1,326 total includes taxes & fees Oct 24 - Oct 25 [](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) ![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) ![Dining](https://images.trvl-media.com/lodging/113000000/112580000/112577500/112577488/c937e03d.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannette M. CA $351 CA $775 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Greenport-Hotels-The-Greenport-Beach-Cottage-3-Min-Walk-To-Beach.h112577488.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/35000000/34420000/34412800/34412732/9bb94097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34420000/34412800/34412732/w2030h3223x0y0-22229895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/35000000/34420000/34412800/34412732/2d21ffbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/35000000/34420000/34412800/34412732/73002c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Town walking distance-Bridgehampton Cottage Bridgehampton 9.4/10 Exceptional (10) "Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim M. [](https://www.expedia.ca/Bridgehampton-Hotels-Town-Walking-Distance-Bridgehampton-Cottage.h34412732.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=2025-11-05&endDate=2025-11-06®ionId=553248621557934296&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top North Main Street Historic District Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Beach Hotel Hotels in Amagansett](https://www.expedia.ca/Amagansett-Hotels-Beach-Hotel.0-0-d73561-tBeachHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Amagansett](https://www.expedia.ca/Amagansett-Hotels-LGBT-Friendly-Hotel.0-0-d73561-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Amagansett](https://www.expedia.ca/Amagansett-Hotels-Oceanfront-Hotels.0-0-d73561-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Amagansett](https://www.expedia.ca/Amagansett-Hotels-Spa-Hotel.0-0-d73561-tSpaHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Brooklyn](https://www.expedia.ca/Brooklyn-Hotels-Beach-Hotel.0-0-d177851-tBeachHotel.Travel-Guide-Filter-Hotels) - 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[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) - [Winery Hotels in East Hampton](https://www.expedia.ca/East-Hampton-Hotels-Winery-Hotel.0-0-d1524-tWineryHotel.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) - 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