Title: Book the Best Roundout WINERY Hotels in 2025 | Expedia.ca [Roundout Travel Guide](https://expedia.ca/Kingston-Roundout.dx908655810427924480)[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)[Roundout Car Rentals](https://expedia.ca/Car-Rentals-In-Roundout.d908655810427924480.Car-Rental-Guide)[Roundout Vacations](https://expedia.ca/Roundout.d908655810427924480.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 Roundout, NY from CA $141 ![](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 Roundout Winery Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=908655810427924480&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=908655810427924480&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=908655810427924480&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=908655810427924480&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Roundout 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) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/dab27d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783222/a9b4d40a.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) ### Hampton Inn by Hilton New Paltz New Paltz 9.4/10 Exceptional (1004) "Excellent choice to stay at in this area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $171 CA $191 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-By-Hilton-New-Paltz.h15783222.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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/130ec357.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 (357) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $159 CA $185 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Living area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/dc93786c.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/1765b81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Poughkeepsie Poughkeepsie 8.8/10 Excellent (1012) "Clean room, staff is friendly especially at the cafe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $147 CA $166 total includes taxes & fees Nov 12 - Nov 13 [](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) ![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) ![Lunch, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/13000000/12620000/12611900/12611810/700c0e5d.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 $186 CA $211 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) ![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) ![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) ![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) ### The Wiltwyck Kingston 9.4/10 Exceptional (162) "Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $156 CA $253 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Kingston-Hotels-The-Wiltwyck.h83964397.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) ![Vending machine](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/3070b4a6.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) ### Quality Inn Poughkeepsie Arlington 7.8/10 Good (460) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $121 CA $141 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Poughkeepsie.h6465.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/f43255d8.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 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 (501) "Lovely stay. Fantastic location by the gunks, new paltz, gardener, and Mohonk. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rakhi CA $296 CA $364 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.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) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99550000/99543900/99543833/9cd00997.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 $138 CA $249 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Saugerties-Hotels-The-Country-Cottage.h99543833.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/92000000/91580000/91577900/91577819/6b02a55c.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) ![Reception](https://images.trvl-media.com/lodging/92000000/91580000/91577900/91577819/bc027e8c.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) ![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) ![Interior](https://images.trvl-media.com/lodging/77000000/76410000/76400200/76400133/4e24f0c1.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) "We enjoyed our stay at this quiet, cozy property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $208 CA $325 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Red-Hook-Hotels-The-Suite-Gallatin-Farmstead-Private.h76400133.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=908655810427924480&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Roundout Hotel Reviews ![Americas Best Value Inn New Paltz](//images.trvl-media.com/lodging/1000000/900000/897900/897882/1c07aec9_y.jpg) ### Americas Best Value Inn New Paltz 10/10 Excellent "We enjoyed our stay, we thought there could have been more choices for breakfast. Like sausage or eggs, etc. Other than that, everything else was good." [](https://expedia.ca/Poughkeepsie-Hotels-Americas-Best-Value-Inn-New-Paltz.h897882.Hotel-Information) ![SureStay Plus Hotel by Best Western Highland Poughkeepsie](//images.trvl-media.com/lodging/1000000/920000/918800/918797/960f4844_y.jpg) ### SureStay Plus Hotel by Best Western Highland Poughkeepsie 10/10 Excellent "Great hotel. New, clean. Pleasant staff. Plenty of parking. " [](https://expedia.ca/Poughkeepsie-Hotels-SureStay-Plus-Hotel-By-Best-Western-Highland-Poughkeepsie.h918797.Hotel-Information) ![Quality Inn Hyde Park Poughkeepsie North](//images.trvl-media.com/lodging/1000000/910000/906700/906700/ea4bff95_y.jpg) ### Quality Inn Hyde Park Poughkeepsie North 10/10 Excellent "NA" [](https://expedia.ca/Poughkeepsie-Hotels-Quality-Inn-Hyde-Park-Poughkeepsie-North.h906700.Hotel-Information) ![Minnewaska Lodge](//images.trvl-media.com/lodging/2000000/1210000/1201800/1201707/3be04d40_y.jpg) ### Minnewaska Lodge 10/10 Excellent "Beautiful room, lobby, dining/sitting area and grounds" [](https://expedia.ca/Poughkeepsie-Hotels-Minnewaska-Lodge.h1201707.Hotel-Information) ![Courtyard by Marriott Poughkeepsie](//images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg) ### Courtyard by Marriott Poughkeepsie 10/10 Excellent "Very clean, nice and convenient to get from car to room. My husband said they had the best shower water pressure he had ever experienced in his entire life. Lol. Awesome stay! Very quiet when we were there. " [](https://expedia.ca/Poughkeepsie-Hotels-Courtyard-By-Marriott-Poughkeepsie.h5910.Hotel-Information) ![Holiday Inn Express Poughkeepsie by IHG](//images.trvl-media.com/lodging/1000000/20000/12200/12157/9d729415_y.jpg) ### Holiday Inn Express Poughkeepsie by IHG 10/10 Excellent "Clean room. Helpful staff. Breakfast was a typical Holiday Inn Express buffet - adequate and replenished as needed. No nearby restaurants so we had to drive 7-8 minutes to get dinner, which wasn’t a big inconvenience. We were there on a Sunday night and many places were closed. " [](https://expedia.ca/Poughkeepsie-Hotels-Holiday-Inn-Express-Poughkeepsie.h12157.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) - [Hotels & Resorts for Couples in Albany](https://www.expedia.ca/Albany-Hotels-Couples-Resorts-Hotels.0-0-d603260-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Albany](https://www.expedia.ca/Albany-Hotels-Hotel-With-Early-Check-In.0-0-d603260-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Bar.0-0-d603260-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Albany](https://www.expedia.ca/Albany-Hotels-Hotels-With-Tennis-Courts.0-0-d603260-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Ski Hotels in Albany](https://www.expedia.ca/Albany-Hotels-Ski-Hotel.0-0-d603260-tSkiHotel.Travel-Guide-Filter-Hotels) - 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