Title: Book the Best Shady WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in Woodstock](https://expedia.ca/Woodstock-Vacation-Rentals.d176573.Travel-Guide-VacationRentals)[Flights to Woodstock](https://expedia.ca/Cheap-Flights-To-Woodstock.d176573.Travel-Guide-Flights)[Things to do in Woodstock](https://expedia.ca/Things-To-Do-In-Woodstock.d176573.Travel-Guide-Activities)[Shady Car Rentals](https://expedia.ca/Car-Rentals-In-Shady.d553248635976471788.Car-Rental-Guide)[Shady Vacations](https://expedia.ca/Shady.d553248635976471788.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Shady, NY from CA $208 ![](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 Shady Winery Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976471788&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shady Winery Hotels ![Front of property](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/ab673905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Motel Style Room with 2 Queen Beds - Pet Friendly](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/af6d3144.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/8bf1ed7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/da41475a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beekman Arms Hotel Rhinebeck 8.2/10 Very good (759) "Fantastic stay, clean, hugh room with fireplace, can walk throughout the town. Great breakfast!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele CA $184 CA $209 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Superior Suite | Living area](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/ecb4d351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Suite | Private kitchenette](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/38d379df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/67e7a8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite | Living area](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/d7e328ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wiltwyck Kingston 9.4/10 Exceptional (162) "Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $149 CA $245 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.Hotel-Information) ![Superior Room, Fireplace, River View](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/a7440a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/4b59784b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/bc027e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/d778d70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Way Hotel Woodstock 9.6/10 Exceptional (195) "Awesome property, cute town and excellent service. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Daryn CA $384 CA $485 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Way-Hotel.h91577819.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/855d7f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/0607b999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/f395be91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/737a2fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Cottage with beautiful views and easy access to Catskills activities. Saugerties 10/10 Exceptional (12) "Great spot!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dylan CA $139 CA $249 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/6c73b5e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/73dcc006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/b2de5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102810000/102808300/102808286/79573e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Experience Peace in this Beautiful country cottage nestled beneath the mountains Catskill 9.8/10 Exceptional (8) "Very comfortable cottage in a lovely area. Grateful for the ac on those very hot days! Loved grilling on the porch and the big patio umbrellas. Host is very responsive and helpful when needed. Hope to come again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura G. CA $208 CA $467 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Catskill-Hotels-Charming-2-Bedroom-House-With-WiFi.h102808286.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/c63bdc52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/e19375ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/33ca2782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78330000/78322000/78321995/a10f3374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill Catskill 9.8/10 Exceptional (32) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steve p. CA $210 CA $461 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Catskill-Hotels-Cozy-Catskill-Cabin-W-10-Minute-Walk-To-Downtown-Catskill.h78321995.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/f9b90241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/593e8eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, stereo](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/256f5f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89610000/89604900/89604830/c4bc1487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Only Ski In Out on Hunter Mtn | Panoramic Views! Hike, Golf, Fish, Recharge Hunter Highlands 9.8/10 Exceptional (6) "If you are looking for a nice place to stay to attend the annual Hunter Mountain Octoberfest this is the place to stay. Very clean, and hosts are very responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia H. CA $137 CA $301 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hunter-Hotels-Catskill-Oasis-II-The-Only-True-Ski-InOut-On-Mtn.h89604830.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/a5431ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/f4d68743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/w450h639x287y44-0aaac327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88870000/88864900/88864808/1f5e7a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Studio at the Inn at High Falls High Falls 8.2/10 Very good (31) "Place is exactly how it looks! Great location between New Paltz, Kingston, Woodstock. We unfortunately had inconsiderate neighbors that forced us leave early, but Frank was incredibly gracious and made it up to us. Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harrison W. CA $157 CA $380 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/High-Falls-Hotels-The-Studio-At-The-Inn-At-High-Falls.h88864808.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86330000/86326200/86326150/a5e03cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/87000000/86330000/86326200/86326150/w1284h722x0y11-acf4b792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/87000000/86330000/86326200/86326150/fe909468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/87000000/86330000/86326200/86326150/3da8d122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sexiest Lil Cabin in Saugerties, NY Saugerties 9.0/10 Wonderful (13) "We loved our stay here, it was the perfect short getaway. Thanks Alexandria!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie L. CA $157 CA $208 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Saugerties-Hotels-Sexiest-Lil-Cabin-In-Saugerties.h86326150.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/8229761f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/1e426647.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/f19c8f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83450000/83440300/83440247/891f2edc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Apartment with Sauna in Historic Stone Ridge Stone Ridge 9.4/10 Exceptional (13) "Clean cozy will be staying again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael C. CA $119 CA $255 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Stone-Ridge-Hotels-Cozy-Apartment-With-Sauna-In-Historic-Stone-Ridge.h83440247.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=2025-11-08&endDate=2025-11-09®ionId=553248635976471788&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Shady Hotel Reviews ![Hotel Vienna](//images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg) ### Hotel Vienna 10/10 Excellent "Beautiful location & property. Nice modern rooms. Nice European accent. Comfortable beds and pillows. 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