Title: Book the Best Chappaqua WINERY Hotels in 2025 | Expedia.ca [Hotels in Chappaqua](https://expedia.ca/Chappaqua-Hotels.d88470.Travel-Guide-Hotels)[Vacation Rentals in Chappaqua](https://expedia.ca/Chappaqua-Vacation-Rentals.d88470.Travel-Guide-VacationRentals)[Chappaqua Car Rentals](https://expedia.ca/Car-Rentals-In-Chappaqua.d88470.Car-Rental-Guide)[Chappaqua Vacation Packages](https://expedia.ca/Chappaqua.d88470.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 Chappaqua, NY from CA $155 ![](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 Chappaqua Winery Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=88470&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chappaqua 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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/da977c85.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) ### Sonesta Simply Suites Nanuet Nanuet 8.4/10 Very good (1020) "Great place to stay!!" CA $134 CA $155 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.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) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/67801e28.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) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands Fort Montgomery 9.8/10 Exceptional (122) "It has an incredible mountain and water view. " CA $263 CA $431 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/9fa76c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/8a733476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/120892ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/95000000/94720000/94717500/94717468/7b3193ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Local Artist Inspired | Walk to WestPoint + King Bed Highland Falls 9.2/10 Wonderful (7) "Stayed for the Easter w/e to visit our cadet son at West Point. % mins from maon street and 10 mins from West Point and the golf course. Clean, spacious and well laid out for 2 adults and 2 teenage kids. Will be looking to stay there again on future visits instead of trying to find hotels that are 25-40 mins drive away." CA $276 CA $723 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Highland-Falls-Hotels-Local-Artist-Inspired-Walk-To-WestPoint-King-Bed.h94717468.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/62b642d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/2af87762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/92f79611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114640000/114637300/114637256/4675a87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3BR Prime Luxury near NYC w Arcade Room Southeast Yonkers 8.0/10 Very good (1) "We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms." CA $839 CA $1,077 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Yonkers-Hotels-3BR-Prime-Luxury-Near-NYC-W-Arcade-Room.h114637256.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/76b5d504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/df2c75ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/fe2ef847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/490a9125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining 8.8/10 Excellent (5) "We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. " CA $1,175 CA $1,908 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Ossining-Hotels-Castle-Cozy-Winter-Wonderland-Events.h101852343.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/d9fd577e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/cf9301a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/78370020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/8f17c18a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility. Waccabuc 2.0/10 (1) CA $179 CA $254 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Waccabuc-Hotels-Cozy-Ground-Floor-Suite-Ideal-For-A-Relaxing-Stay-Enjoy-Peace-And-Tranquility.h119145159.Hotel-Information) ![Blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114720000/114714100/114714091/333a4576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114720000/114714100/114714091/068a3fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114720000/114714100/114714091/f27fcf05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/115000000/114720000/114714100/114714091/65dc72b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultra-Modern Luxe Sleek & Stunning Stay White Plains 2.0/10 (1) CA $819 CA $913 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/White-Plains-Hotels-Ultra-Modern-Luxe-Sleek-Stunning-Stay.h114714091.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=2025-10-27&endDate=2025-10-28®ionId=88470&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chappaqua Hotel Reviews ![Ardsley Acres Hotel Westchester](//images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 10/10 Excellent "The heating is very weak. Must improve before freezing weather. Would be nice to have more than two sets of towels for two occupants" [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Awesome staff and beautiful room" [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![West Gate Inn Nyack](//images.trvl-media.com/lodging/6000000/5850000/5843400/5843352/393dcf26_y.jpg) ### West Gate Inn Nyack 10/10 Excellent "Staff was extreamly friendly. Great breakfast buffett. " [](https://expedia.ca/Nyack-Hotels-West-Gate-Inn-Nyack.h5843352.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](//images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "They had free cookies. " [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](//images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "I have stayed here many times It is central to everything Clean ,pleasant ,efficient and professional On this particular stay the night desk clerk and the housekeeping staff were extremely helpful and nice " [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Beach-Hotel.0-0-d9324-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Cheap-Hotels.0-0-d9324-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Armonk](https://www.expedia.ca/Armonk-Hotels-Golf-Hotel.0-0-d9324-tGolfHotel.Travel-Guide-Filter-Hotels) - 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