Title: Book the Best Darien WINERY Hotels in 2025 | Expedia.ca [Hotels in Darien](https://expedia.ca/Darien-Hotels.d7557.Travel-Guide-Hotels)[Vacation Rentals in Darien](https://expedia.ca/Darien-Vacation-Rentals.d7557.Travel-Guide-VacationRentals)[Flights to Darien](https://expedia.ca/Cheap-Flights-To-Darien.d7557.Travel-Guide-Flights)[Darien Car Rentals](https://expedia.ca/Car-Rentals-In-Darien.d7557.Car-Rental-Guide)[Darien Vacation Packages](https://expedia.ca/Darien.d7557.Destination-Travel-Guides) ![Nice beach, picnic tables. Park done the street if you don't have the Darien sticker. ](https://images.trvl-media.com/place/7557/83dbfd26-5696-4a63-bb13-31b0d6b47a49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tim Rousseau # Find Winery Hotels in Darien, CT from CA $237 - ![](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 Darien Winery Hotels Tonight [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=7557&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=7557&startDate=2025-11-07&endDate=2025-11-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7557&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7557&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Darien Winery Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2220000/2210600/2210572/8a009742.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/3000000/2220000/2210600/2210572/0ef09a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2220000/2210600/2210572/0802122b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2220000/2210600/2210572/0420e809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Melville Plainview 8.8/10 Excellent (1001) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Niarobi CA $207 CA $237 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Plainview-Hotels-Hilton-Garden-Inn-Melville.h2210572.Hotel-Information) ![Smart TV, fireplace, table tennis, computer monitors](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/11c0d934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/346e3932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/7b672dc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/82000000/81830000/81827600/81827580/dfe354b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Cottage - Cold Spring Harbor Water Views Cold Spring Harbor 10/10 Exceptional (70) "Great home to stay. Beautiful area to explore!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy W. CA $282 CA $656 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Cold-Spring-Harbor-Hotels-Captains-Cottage-Cold-Spring-Harbor-Water-Views.h81827580.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) ![Pool](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/490a9125.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) ![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) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining 9.0/10 Wonderful (6) "This is an incredibly unique property with some upsides. It is a cool old (1920's) Tudor style house that is well-suited for large groups. While it was fine for a couple of nights, any longer would have made the downsides (deferred maintenance, insufficient silverware, stained carpeting) less tolerable. There were also some communication issues with the property management company and the host during the stay. Specifically, we counted on there being a crib available, as it was specified in the... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marnie O. CA $1,168 CA $1,960 total includes taxes & fees Dec 2 - Dec 3 [](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) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/ba6c1ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119150000/119145200/119145159/f8330815.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) ### Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility. Waccabuc 4.0/10 (2) "Clean but minimalist, big empty basement, good for a cheap stay near Caramoor" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick M. CA $208 CA $288 total includes taxes & fees Nov 10 - Nov 11 [](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) ![Private kitchen](https://images.trvl-media.com/lodging/115000000/114720000/114714100/114714091/6cd14839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultra-Modern Luxe Sleek & Stunning Stay White Plains 2.0/10 (1) CA $742 CA $827 total includes taxes & fees Nov 27 - Nov 28 [](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=2025-11-20&endDate=2025-11-21®ionId=7557&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Darien Hotel Reviews ![Tarrytown House Estate](//images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "The view from the balcony was amazing " [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Ardsley Acres Hotel Westchester](//images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 10/10 Excellent "Was in town Halloween over night to go to Tarrytown/Sleepy Hollow which is an easy 10 minute drive from the hotel. The property was very clean and cozy. Check in was easy and receptionist was Friendly. The room was clean and very comfortable. Easy access to dining and highways. Breakfast was basically breads, cereal and coffee. But there is Starbucks and breakfast options within half mile. Definitely a great stay. Would recommend. " [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Sonesta White Plains Downtown](//images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Excellent guest service. Room was very clean. Always stay at the Sonesta when I am traveling to NY." [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Sleepy Hollow Hotel](//images.trvl-media.com/lodging/1000000/10000/4000/3956/ee0f5c7a_y.jpg) ### Sleepy Hollow Hotel 10/10 Excellent "Was very nice!! Would definitely visit again" [](https://expedia.ca/White-Plains-Hotels-Sleepy-Hollow-Hotel-Conference-Center.h3956.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 "Breakfast was great..Great temperature..Fruits were fresh..Staff was very friendly.The heat was great..Its winter.Indoor needs heat" [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.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 "." 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[Stamford Hotels](https://www.expedia.ca/Stamford-Hotels.d602523.Travel-Guide-Hotels) - [Inns in Stamford](https://www.expedia.ca/Stamford-Inns.d602523-aaInns.Travel-Guide-Accommodation) - [Lodges in Stamford](https://www.expedia.ca/Stamford-Lodges.d602523-aaLodges.Travel-Guide-Accommodation) - [Motels in Stamford](https://www.expedia.ca/Stamford-Motels.d602523-aaMotels.Travel-Guide-Accommodation) - [Residences in Stamford](https://www.expedia.ca/Stamford-Residences.d602523-aaResidences.Travel-Guide-Accommodation) - [Hotels near Stamford Town Center](https://www.expedia.ca/Stamford-Town-Center-Hotels.0-l6125753-0.Travel-Guide-Filter-Hotels) - [Hotels near The Maritime Aquarium](https://www.expedia.ca/The-Maritime-Aquarium-Hotels.0-l553248621555566147-0.Travel-Guide-Filter-Hotels) - [Hotels near The SoNo Collection](https://www.expedia.ca/The-SoNo-Collection-Hotels.0-l759370593496035328-0.Travel-Guide-Filter-Hotels) - [Flights to Norwalk](https://www.expedia.ca/Cheap-Flights-To-Norwalk.d9245.Travel-Guide-Flights) - [Flights to Rowayton](https://www.expedia.ca/Cheap-Flights-To-Rowayton.d3000430454.Travel-Guide-Flights) - [Flights to Stamford](https://www.expedia.ca/Cheap-Flights-To-Stamford.d602523.Travel-Guide-Flights) - [Flights from Stamford](https://www.expedia.ca/lp/flights/602523/flights-from-stamford) - [Flights from Norwalk Islands](https://www.expedia.ca/lp/flights/6347888/flights-from-norwalk-islands) - [Flights from Norwalk](https://www.expedia.ca/lp/flights/9245/flights-from-norwalk) - [Norwalk Islands Vacations](https://www.expedia.ca/Norwalk-Islands.d6347888.Destination-Travel-Guides) - [Visit Norwalk Islands](https://www.expedia.ca/Norwalk-Islands.dx6347888) - [Sheffield Island Lighthouse](https://www.expedia.ca/Sheffield-Island-Lighthouse-Connecticut.d553248621558114961.Vacation-Attraction) - [Visit Sheffield Island](https://www.expedia.ca/Sheffield-Island.dx6353650) - [Stamford Vacations](https://www.expedia.ca/Stamford.d602523.Destination-Travel-Guides) - [Visit Stamford](https://www.expedia.ca/Stamford.dx602523) - [Alamo Rent A Car Rental Cars in Norwalk Islands](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Norwalk-Islands.d6347888-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Norwalk](https://www.expedia.ca/Avis-Car-Rentals-In-Norwalk.d9245-c41.Car-Rental-Guide-Suppliers) - [Car rental Norwalk](https://www.expedia.ca/Car-Rentals-In-Norwalk.d9245.Car-Rental-Guide) - [Car rental Stamford](https://www.expedia.ca/Car-Rentals-In-Stamford.d602523.Car-Rental-Guide) - [Hertz Rental Cars in Norwalk Islands](https://www.expedia.ca/Hertz-Car-Rentals-In-Norwalk-Islands.d6347888-c40.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in Norwalk Islands](https://www.expedia.ca/Payless-Car-Rentals-In-Norwalk-Islands.d6347888-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Norwalk](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Norwalk.d9245-c33.Car-Rental-Guide-Suppliers) - [Norwalk Islands Vacation Rentals](https://www.expedia.ca/Norwalk-Islands-Vacation-Rentals.d6347888.Travel-Guide-VacationRentals) - [Norwalk Vacation Rentals](https://www.expedia.ca/Norwalk-Vacation-Rentals.d9245.Travel-Guide-VacationRentals) - [Things to do in Stamford](https://www.expedia.ca/Things-To-Do-In-Stamford.d602523.Travel-Guide-Activities) - [Book Winery Hotels in Darien on Expedia.com](https://www.expedia.com/Darien-Hotels-Winery-Hotel.0-0-d7557-tWineryHotel.Travel-Guide-Filter-Hotels)