Title: Book the Best Chester WINERY Hotels in 2025 | 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) ![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 Chester, NY from CA $156 - ![](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 [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6046665&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Winery Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/46d5cbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/213a567d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a6bae724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Simply Suites Nanuet Nanuet 8.4/10 Very good (1058) "great place for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ramon CA $149 CA $173 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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) ![View from property](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/25051ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11800000/11796100/11796055/91f0a8ce.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 Montgomery 9.2/10 Wonderful (140) "Our room was clean, comfortable, and cozy. The staff was so kind. Breakfast was awesome! We had a wedding at City Winery so location was also perfect. Would highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis [](https://www.expedia.ca/Newburgh-Hotels-Borland-House-Inn.h11796055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/fe354234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/dc5981dc.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) ### Holiday Inn Express & Suites Montgomery by IHG Montgomery 8.8/10 Excellent (778) "Location to venue we were attending. Room size was perfect and clean! Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $150 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-Suites-Montgomery.h7814618.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/e1e7e350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2f2f704a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/459515b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/890500/890436/2831de3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Fishkill Fishkill 8.6/10 Excellent (1019) "Very clean and updated facilities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $138 CA $156 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hilton-Garden-Inn-Fishkill.h890436.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) ![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/fe94434f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17270000/17262200/17262186/11f1915d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Newburgh Stewart Airport Newburgh 9.2/10 Wonderful (958) "It was very clean.. friendly check in/ desk people.. great safety features in the bathroom.. comfortable bed. Will stay again !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) amy CA $160 CA $189 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Suites-Newburgh-Stewart-Airport.h17262186.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/2a01f3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/9b9c3b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/b3546f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Newburgh Stewart Airport Newburgh 8.2/10 Very good (691) "Property clean rooms clean front desk the Best " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dirwin CA $142 CA $167 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Newburgh-Hotels-Courtyard-By-Marriott-Newburgh-Stewart-Airport.h42673.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/b3c97637.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) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/fd01a6d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83430000/83426500/83426410/475d7ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dream getaway apartment in the foot of Gunks Ridge Wallkill 9.6/10 Exceptional (23) "This was such a great option for us as we were only in town for the night for a haunted house attraction. The space is extremely spacious, very nicely decorated and gave us the fall season feeling. A great stay and would definitely do it again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal L. CA $105 CA $257 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Wallkill-Hotels-Dream-Getaway-Apartment-In-The-Foot-Of-Gunks-Ridge.h83426410.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) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83400000/83395700/83395605/a0a87ff4.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) ### The DeVita House Est. 1900 Gardiner 10/10 Exceptional (31) "We loved our stay at this rental. The house was cozy and very clean. The neighborhood was quiet and had amazing scenery. We will definitely book this house again in the future!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hilary T. CA $210 CA $622 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Gardiner-Hotels-The-DeVita-House-Est-1900.h83395605.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/f57ee72e.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/1000000/120000/119300/119273/8529e0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/w3831h2553x9y7-9c25ee45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/120000/119300/119273/0c0edcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Fishkill Fishkill 8.6/10 Excellent (1002) "Was convenient. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy CA $163 CA $185 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Poughkeepsie-Hotels-Hampton-Inn-Fishkill.h119273.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108750000/108747000/108746993/155035bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108750000/108747000/108746993/b6757000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108750000/108747000/108746993/w1079h959x0y0-752079e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108750000/108747000/108746993/w1080h959x0y1-22442b90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Hudson Valley Retreat Near Mohonk Plattekill 10/10 Exceptional (2) "Beautiful location and great stay! Would come here again in a heartbeat. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gavin [](https://www.expedia.ca/Wallkill-Hotels-The-Sapling-At-Forest.h108746993.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=2025-11-15&endDate=2025-11-16®ionId=6046665&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Hampton Inn Harriman Woodbury](//images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Very clean hotel , friendly staff and convenient to shopping. We will definitely stay here again. " [](https://expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ## Frequently asked questions ### How much does a winery hotel in Chester cost? > Enjoy staying in a winery hotel in Chester, with plenty of hotels from CA $156 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays. ### Which area of Chester is best to stay in for vineyards and wineries? > The Hudson Valley region, particularly around Chester, New York, is a delightful choice for wine enthusiasts seeking to explore picturesque vineyards and wineries. This charming area is home to several award-winning wineries set against a backdrop of rolling hills and scenic landscapes. From the renowned Brotherhood Winery, the oldest in America, to the quaint Tasting Room at Glorie Farm Winery, each location offers a great experience and a chance to sample exquisite local wines. > > > > 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? > Chester, New York, is a hidden gem for wine enthusiasts, located in the picturesque Hudson Valley. This charming town offers a delightful selection of wineries, where you can experience the local viticulture and enjoy breathtaking views of the surrounding landscapes. Renowned for its artisanal approach, Chester's wineries often feature tastings of unique blends and varietals, showcasing the region's commitment to quality. > > > > 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? > Chester, New York, is a charming town located in the scenic Hudson Valley, known for its stunning landscapes and vibrant local culture. This delightful area is home to several wine festivals and events that celebrate the rich viticulture of the region. Each year, the Hudson Valley Wine & Food Festival draws visitors from near and far, showcasing an impressive selection of local wineries, craft breweries, and artisanal food vendors. Set against the backdrop of the beautiful autumn foliage, this festival is a feast for the senses, offering tastings, live music, and culinary demonstrations. > > > > 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? > Members always get our best prices. Find our best Chester hotel deals by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's free travel rewards program. As a member, you can unlock instant savings and member perks when you're signed in. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too. ### Is it cheaper to book flights and a winery hotel in Chester as a package deal? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my winery hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel winery hotel in Chester for you. ## 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) - [Beach Hotel Hotels in Central New York City](https://www.expedia.ca/Central-New-York-City-New-York-Hotels-Beach-Hotel.0-n553248633938969338-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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