Title: Book the Best Chester WINERY Hotels in 2026 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6046665.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6046665.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6046665.Destination-Travel-Guides) ![Black dirt region farm Chester New York](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046665/d9882a23-1cf5-416b-8c04-b5101f7be1f4.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Chester Winery Hotels Tonight [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-14&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels with winery ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/7ce1352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/61a8edaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/a69379da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/e358b978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Central Valley - Woodbury [](https://www.expedia.ca/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.Hotel-Information) Central Valley 7.6/10 Good (16 reviews) "The cleaning could have been better" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuna CA $134 CA $165 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/47637293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/2154c327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/20894557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/49ef52ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borland House Inn [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) Montgomery 9.2/10 Wonderful (155 reviews) "Our room was beautiful and well maintained and spotlessly clean. I did not realize before we came to the hotel that the bathroom was out in the hall, not en suite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/605b2de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/f3b7bb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/abf8ab38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Montgomery by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) Montgomery 8.8/10 Excellent (832 reviews) "clean, warm room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $117 CA $133 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/3df08b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/275854de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/e34f60f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/000bcb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Newburgh Stewart Airport [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) Newburgh 9.2/10 Wonderful (1,001 reviews) "Wonderful accommodations!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne CA $155 CA $183 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/3b6f022d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e02a568f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/f4de9a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) Fishkill 8.6/10 Excellent (1,001 reviews) "Room was beautifully spotless. Enjoyed everything during my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francine CA $133 CA $151 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/4c32f4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w906h683x59y0-429ea470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w904h683x60y0-c79d6146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90899500/90899463/w1024h680x0y3-a7b1dcac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in the heart of the Hudson Valley, Cabin 4 [](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.Hotel-Information) Newburgh 9.0/10 Wonderful (26 reviews) "We LOVE this place and have stayed here twice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer w. CA $175 CA $271 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90899463.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.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/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (132 reviews) "Amazing place Thanks for the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien C. CA $256 CA $417 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/b2f29274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/eb48d384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/54004000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) Goshen 9.8/10 Exceptional (13 reviews) "Great place to stay when visiting Legoland. Convenient location and comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica C. CA $202 CA $403 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/10d69ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/877cc95b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/0c3ccbf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/cb371140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dream getaway apartment in the foot of Gunks Ridge [](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information) Wallkill 9.6/10 Exceptional (24 reviews) "Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary S. CA $74 CA $221 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.Hotel-Information) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y2-21ff539b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-d877abc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h680x0y3-8188dd85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90900000/90897800/90897766/w1024h681x0y0-cfce0679.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in the Heart of the Hudson Valley, Cabin 1 [](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.Hotel-Information) Newburgh 10/10 Exceptional (32 reviews) "Great overnight spot, especially with a dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed C. CA $230 CA $384 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Newburgh-Hotels-Cabin-In-The-Heart-Of-The-Hudson-Valley.h90897766.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=2026-03-27&endDate=2026-03-28®ionId=6046665&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_6046665) ## Top Chester Hotel Reviews ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg) ### Courtyard by Marriott Newburgh Stewart Airport 10/10 Excellent "Very clean" [](https://expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Great plave" [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Chester cost? ### Which area of Chester is best to stay in for vineyards and wineries? > For couples looking for a romantic escape, the serene setting of Chester's wineries provides the great atmosphere. Imagine strolling hand-in-hand through vineyards, enjoying a wine tasting, and perhaps sharing a gourmet picnic on the grounds. Many wineries also host special events, such as live music and seasonal festivals, adding to the charm of your getaway. > > > Families will appreciate the family-friendly vibe of this area. Many wineries offer outdoor spaces for children to play, along with educational tours that engage visitors of all ages. The nearby Hudson Highlands offer hiking trails and breathtaking views, making it easy to combine outdoor adventure with your vineyard visits. ### What winery activities should we do in Chester? > For couples seeking a romantic outing, a visit to the nearby Brotherhood Winery is a must. Established in 1839, it is the oldest continuously operating winery in the United States. You can stroll through the scenic grounds before indulging in a guided tasting of their exquisite wines. The winery also hosts events and live music, making it an ideal setting for a special evening together. > > > Families will find fun at the scenic Whitecliff Vineyard and Winery, where kids can enjoy the expansive outdoor space while parents sip on award-winning wines. The vineyard often hosts family-friendly events, including picnics and seasonal festivals, allowing everyone to enjoy a day in the sun while learning about the winemaking process. > > > Lastly, if you're a foodie, don't miss the opportunity to pair local wines with delicious fare at the various vineyard restaurants. Many offer farm-to-table dining experiences that highlight the region's rich agricultural bounty, providing a superb complement to the wines and a memorable culinary adventure. ### Does Chester host any wine festivals or events? > For couples seeking a romantic experience, the Hudson Valley is dotted with picturesque wineries that offer intimate tastings and vineyard tours. Places like Brotherhood Winery, the oldest in the U.S., provide not only exquisite wines but also stunning views, making for a great day out together. > > > Families can enjoy the lively option of Chester's various local events throughout the year. The annual Chester Harvest Festival features local crafts, delicious food, and fun activities for all ages, ensuring that everyone has a memorable time. ### How can I save on a winery hotel in Chester with Expedia? ### Is it cheaper to book flights and a winery hotel in Chester as a package deal? ### Can I cancel my winery hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Cheap-Hotels.0-0-d3000448042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Blooming Grove ](https://www.expedia.ca/Blooming-Grove-Hotels-Hotels-With-Free-Breakfast.0-0-d3000448042-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Campbell Hall ](https://www.expedia.ca/Campbell-Hall-Hotels-Cheap-Hotels.0-0-d6338665-tCheapHotels.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central New York City ](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Adults-Only-Resorts.0-n553248633938969338-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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