Title: Book the Best Hillside WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in Kingston](https://expedia.ca/Kingston-Vacation-Rentals.d6056321.Travel-Guide-VacationRentals)[Flights to Kingston](https://expedia.ca/Cheap-Flights-To-Kingston.d6056321.Travel-Guide-Flights)[Things to do in Kingston](https://expedia.ca/Things-To-Do-In-Kingston.d6056321.Travel-Guide-Activities)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d553248634998735142.Car-Rental-Guide)[Hillside Vacations](https://expedia.ca/Hillside.d553248634998735142.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/winery.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Hillside, NY from CA $137 - ![](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 Hillside Winery Hotels Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=553248634998735142&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=553248634998735142&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248634998735142&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248634998735142&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Hillside Winery Hotels ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bd59d6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/7df797b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/bdaa6450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton New Paltz New Paltz 9.4/10 Exceptional (1011) "Clean, comfortable, wonderful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $155 CA $174 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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) ![Front of property](https://images.trvl-media.com/lodging/84000000/83970000/83964400/83964397/f320203a.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) ### The Wiltwyck Kingston 9.4/10 Exceptional (162) "Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/1732edca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Accessible (Hearing)](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4eb66254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/4ae12198.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites By Hilton Poughkeepsie Poughkeepsie 9.4/10 Exceptional (385) "pleasant, quick check in, lovely room, excellent breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $152 CA $176 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/a90c96fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/2b66e26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1010) "Clean room, staff is friendly especially at the cafe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $130 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![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 and Delamater Inn Rhinebeck 8.4/10 Very good (795) "Really enjoyed staying at this lovely property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $139 CA $158 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Beekman-Arms-Hotel.h12611810.Hotel-Information) ![Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/9bb5ee16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/ab0fe1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/3070b4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Poughkeepsie Arlington 7.8/10 Good (493) "staff was very nice and everything was quiet and very clean. a quiet chilling vibe" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $118 CA $137 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101862/40f37484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101862/5ad5462c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101862/a7bf520e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101862/0696e32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (626) "Spacious, clean suite. Convenient parking. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $165 CA $192 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Poughkeepsie-Hotels-Residence-Inn-By-Marriott-Poughkeepsie.h1101862.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/074ac974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/b15ad723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/1e2f9086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/56c0072d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the suite @ barn & bike - private, bucolic, serene setting Red Hook 9.8/10 Exceptional (14) "The hosts were great communicators! The space was artistic with a relaxing vibe. Comfortable, quiet and clean. We would love to return for another stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine B. CA $177 CA $230 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.Hotel-Information) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83400000/83395700/83395605/d8b001d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83400000/83395700/83395605/be5fc0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83400000/83395700/83395605/w4124h6192x0y0-e063a571.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83400000/83395700/83395605/a0a87ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The DeVita House Est. 1900 Gardiner 10/10 Exceptional (32) "Gorgeous country home! Highly recommend staying in the DeVita House. Beautiful country setting. You can get lost just watching the pond activity. The area is full of activities and local farms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim J. CA $210 CA $623 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Gardiner-Hotels-The-DeVita-House-Est-1900.h83395605.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/5166d865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/36202057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/36df0c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Minnewaska Lodge Gardiner 9.0/10 Wonderful (520) "Wonderful! Gorgeous scenic atmosphere, friendly welcoming, relaxing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $175 CA $215 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.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=2025-12-15&endDate=2025-12-16®ionId=553248634998735142&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Hillside Hotel Reviews ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg) ### Hampton Inn & Suites Poughkeepsie 10/10 Excellent "The staff was very nice and accommodating. The room was perfect and the bed was super comfortable. Will stay again if in the area." [](https://expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Suites-Poughkeepsie.h1927088.Hotel-Information) ![Minnewaska Lodge](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Very nice place where they cater to everyone as more than a guest, Staff wonderful. Quiet location, so not many choices for restaurants. " [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](https://images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Staff was great. Rooms were updated. Shower heads were the big rain shower type. The beds were comfortable, not too soft. Breakfast buffet was a notch above others. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Pleasant staff and clean room." [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Americas Best Value Inn New Paltz](https://images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "It was fine." [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](https://images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "Great stay " [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](https://images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Nice room, nice staff" [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - More ways to book - [Business Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Business-Hotel.0-0-d603260-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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