Title: Book the Best Montauk WINERY Hotels in 2025 | Expedia.ca [Montauk Travel Guide](https://expedia.ca/Montauk.dx10637)[Hotels in Montauk](https://expedia.ca/Montauk-Hotels.d10637.Travel-Guide-Hotels)[Vacation Rentals in Montauk](https://expedia.ca/Montauk-Vacation-Rentals.d10637.Travel-Guide-VacationRentals)[Flights to Montauk](https://expedia.ca/Cheap-Flights-To-Montauk.d10637.Travel-Guide-Flights)[Things to do in Montauk](https://expedia.ca/Things-To-Do-In-Montauk.d10637.Travel-Guide-Activities)[Montauk Car Rentals](https://expedia.ca/Car-Rentals-In-Montauk.d10637.Car-Rental-Guide)[Montauk Vacation Packages](https://expedia.ca/Montauk.d10637.Destination-Travel-Guides) ![Ditch Plains Beach featuring general coastal views, a beach and surfing](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252399-Montauk.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Montauk, NY from CA $205 ![](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 Montauk Winery Hotels Tonight [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=10637&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=10637&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=10637&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10637&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Montauk Winery Hotels ![1 bedroom, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1680000/1677600/1677542/dd52a5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1680000/1677600/1677542/a2f7080b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1680000/1677600/1677542/5c3f324b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/2000000/1680000/1677600/1677542/2af61719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sandy Shore Motel Westerly 8.2/10 Very good (509) "Great location and staff were great, friendly and helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sonia CA $181 CA $205 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Westerly-Hotels-Sandy-Shore-Motel.h1677542.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103440000/103433100/103433001/fb722c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103440000/103433100/103433001/727e2f9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103440000/103433100/103433001/089fcf03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103440000/103433100/103433001/848ac1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stevedore Landing-#3 · walk downtown Mystic · train · aquarium Stonington 10/10 Exceptional (4) "We enjoyed our stay. The apartment is in excellent condition." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcell CA $106 CA $300 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Mystic-Hotels-Stevedore-Landing-3-Walk-Downtown-Mystic-Train-Aquarium.h103433001.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301938/c26a3cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301938/eea8ba9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301938/8d505492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301938/dc419098.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2 Stonington 10/10 Exceptional (5) "Great stay with friends! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle V. CA $121 CA $320 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Mystic-Hotels-The-Oar-Cottage.h105301938.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) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.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) ### 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 $604 total includes taxes & fees Nov 2 - Nov 3 [](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/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) ![Building design](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sag Harbor Inn Sag Harbor 9.4/10 Exceptional (561) "We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $263 CA $301 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.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 | Living area](https://images.trvl-media.com/lodging/3000000/2870000/2861900/2861838/1fbed560.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian 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/56000000/55540000/55534300/55534224/0c7b10a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/56000000/55540000/55534300/55534224/7f13a2b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/56000000/55540000/55534300/55534224/95754778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55540000/55534300/55534224/8c52505a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super Cute & Cozy Apartment in Downtown Mystic! Mystic 9.6/10 Exceptional (79) "Perfect weekend getaway for my girlfriend and me. Walking distance to downtown on a quiet street. Host was very responsive and even left snacks! We would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anders D. CA $126 CA $294 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Mystic-Hotels-Super-Cute-Cozy-Apartment-In-Downtown-Mystic.h55534224.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34280000/34275400/34275364/f691f570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34280000/34275400/34275364/6c3f4c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34280000/34275400/34275364/23e805b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34275400/34275364/c7cdf2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1845 Home in the Heart of Mystic – Walk to Everything! Mystic 9.8/10 Exceptional (157) "Great Location! Within walking distance to all the sights in Mystic!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamye B. CA $197 CA $428 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Mystic-New-London-Hotels-Unbeatable-Downtown-Mystic-Location-Funky-Decor.h34275364.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/92000000/91070000/91069000/91068954/65a8ebbf.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) ### 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 $409 CA $468 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116990000/116983000/116982931/138dbf0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116990000/116983000/116982931/1eb267df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116990000/116983000/116982931/92e37eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116990000/116983000/116982931/87d1038a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington Stonington 10/10 Exceptional (1) "We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerri P. CA $210 CA $451 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Pawcatuck-Hotels-A-Tiny-Escape-Charming-Eco-Friendly-Retreat-Awaits-In-Stonington.h116982931.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=2025-11-10&endDate=2025-11-11®ionId=10637&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Montauk Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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) - [Casino Hotels in Barnes Landing](https://www.expedia.ca/Barnes-Landing-East-Hampton-Hotels-Casino-Hotel.0-n553248635976472101-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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