Title: Book the Best Jamesport WINERY Hotels in 2025 | Expedia.ca [Hotels in Jamesport](https://expedia.ca/Jamesport-Hotels.d6323751.Travel-Guide-Hotels)[Vacation Rentals in Jamesport](https://expedia.ca/Jamesport-Vacation-Rentals.d6323751.Travel-Guide-VacationRentals)[Things to do in Jamesport](https://expedia.ca/Things-To-Do-In-Jamesport.d6323751.Travel-Guide-Activities)[Jamesport Car Rentals](https://expedia.ca/Car-Rentals-In-Jamesport.d6323751.Car-Rental-Guide)[Jamesport Vacation Packages](https://expedia.ca/Jamesport.d6323751.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/060a16d1d875e7287a13e6f7c8f27fcb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Nina Dinoff # Find Winery Hotels in Jamesport, NY from CA $202 ![](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 Jamesport Winery Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6323751&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6323751&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6323751&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=6323751&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Jamesport Winery Hotels ![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) ![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) ![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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/6b467104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5f09bd5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5a99aefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, pillowtop beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376205/5d4f757e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Long Island-East End by IHG Riverhead 8.6/10 Excellent (1004) "Excellent facility and staff. Room was spacious and extremely clean. Look forward to staying here every trip to Long Island!" CA $207 CA $236 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Riverhead-Hotels-Holiday-Inn-Express-Hotel-Suites-Long-Island-East-End.h1376205.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/11000000/10220000/10211600/10211593/6142ad8a.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) ![Exterior](https://images.trvl-media.com/lodging/11000000/10220000/10211600/10211593/a37c2d73.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 16 - Oct 17 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bowens-By-The-Bays.h10211593.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) ![Fishing](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/eb1df3cc.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) ### 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 16 - Oct 17 [](https://www.expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.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) ![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) ### The Bentley Hotel Southampton Southampton 9.6/10 Exceptional (354) "Really nice room, reasonably priced and very clean " CA $211 CA $241 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116880000/116876700/116876666/73104486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116880000/116876700/116876666/17153fd5_edited_c39b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116880000/116876700/116876666/7977ff38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/117000000/116880000/116876700/116876666/85b5ebee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach Mastic 10/10 Exceptional (4) "Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!" CA $126 CA $257 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Mastic-Hotels-Charming-1-Bedroom-Apartment-20-Minutes-From-The-Hamptons-10-Minutes-From-Beach.h116876666.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) ![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) ![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) ![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) "Had a great stay here with a small group. Host was very accommodating and responsive. " CA $246 CA $615 total includes taxes & fees Oct 16 - Oct 17 [](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) ![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/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) ### 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) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/23000000/22130000/22122500/22122431/139578dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22130000/22122500/22122431/f4228cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/23000000/22130000/22122500/22122431/165205d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/23000000/22130000/22122500/22122431/eaa18051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!! Calverton 9.4/10 Exceptional (41) "I went with family for a memorial celebration for a family member who had passed away. Worked out great and enjoyed the back deck & fire pit! Also, beds were comfy and open kitchen & LR were great for entertaining! Thank you Billy:)" [](https://www.expedia.ca/Calverton-Hotels-Renovated-Cozy-Chic-North-Fork-Cottage.h22122431.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) ![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) ![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) ### Silver Sands Motel & Beach Bungalows Greenport 9.8/10 Exceptional (136) "Great hotel and location. " CA $363 CA $415 total includes taxes & fees Oct 22 - Oct 23 [](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=2025-10-29&endDate=2025-10-30®ionId=6323751&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Jamesport Hotel Reviews ![Greenview Inn Riverhead](//images.trvl-media.com/lodging/2000000/1380000/1374000/1373980/d1b868c8_y.jpg) ### Greenview Inn Riverhead 10/10 Excellent "Really clean and new!" [](https://expedia.ca/Riverhead-Hotels-Greenview-Inn-Riverhead.h1373980.Hotel-Information) ![Hilton Garden Inn Riverhead](//images.trvl-media.com/lodging/2000000/1970000/1962600/1962521/82ff92d7_y.jpg) ### Hilton Garden Inn Riverhead 10/10 Excellent "Great atmosphere. Friendly service. Great room. A pleasure to stay here!" [](https://expedia.ca/Riverhead-Hotels-Hilton-Garden-Inn-Riverhead.h1962521.Hotel-Information) ![Hotel Indigo East End by IHG](//images.trvl-media.com/lodging/4000000/3480000/3475700/3475618/75016698_y.jpg) ### Hotel Indigo East End by IHG 10/10 Excellent "Great experience, loved the bartender and happy hour. Very friendly staff ." [](https://expedia.ca/Riverhead-Hotels-Hotel-Indigo-East-End.h3475618.Hotel-Information) ![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. " [](https://expedia.ca/Sag-Harbor-Hotels-Barons-Cove.h1148848.Hotel-Information) ![Budget Host East End Hotel in Riverhead](//images.trvl-media.com/lodging/2000000/1140000/1130500/1130479/ad0c5cd3_y.jpg) ### Budget Host East End Hotel in Riverhead 10/10 Excellent "You get a lot for a reasonable price. It even has a nice swimming pool." [](https://expedia.ca/Riverhead-Hotels-Budget-Host-East-End-Hotel-In-Riverhead.h1130479.Hotel-Information) ![Hyatt Place Long Island East End](//images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/9bf973cb_y.jpg) ### Hyatt Place Long Island East End 10/10 Excellent "This was a pleasant surprise of a stay! Very clean, central to places to eat, right on the water, and just overall a great stay." 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