Title: Book the Best Chester WINERY Hotels in 2025 | Expedia.ca [Chester Travel Guide](https://expedia.ca/Chester.dx6590)[Hotels in Chester](https://expedia.ca/Chester-Hotels.d6590.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6590.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.ca/Cheap-Flights-To-Chester.d6590.Travel-Guide-Flights)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d6590.Travel-Guide-Activities)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6590.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6590.Destination-Travel-Guides) ![Chester showing night scenes, street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/162000/162415-Chester.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chester from CA $189 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6590&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6590&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6590&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6590&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Winery Hotels ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/200000/190800/190780/04dacf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/200000/190800/190780/ea8e65b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/200000/190800/190780/b72cabf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/200000/190800/190780/2417cd73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carden Park Chester 9.0/10 Wonderful (1000) "The Vines restaurant is excellent in all aspects, food and service makes the experience really special. " CA $209 CA $251 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chester-Hotels-Carden-Park.h190780.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23560000/23551600/23551573/c0517fb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/24000000/23560000/23551600/23551573/c0320ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23560000/23551600/23551573/cf5f2f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23560000/23551600/23551573/61cf1868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super spacious barn conversion with Log fire and hot tub Chester 8.6/10 Excellent (66) "Accommodation was very nice, great views from bbq and hot tub area, not far from city centre either" CA $167 CA $497 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chester-Hotels-Super-Spacious-Barn-Conversion-With-Free-Wifi.h23551573.Hotel-Information) ![Deluxe Apartment, 1 Double Bed, City View | Living area](https://images.trvl-media.com/lodging/79000000/78400000/78395600/78395505/100d3bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 1 Double Bed | Private kitchen](https://images.trvl-media.com/lodging/79000000/78400000/78395600/78395505/910217d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Penthouse, 2 Bedrooms, Ensuite, City View](https://images.trvl-media.com/lodging/79000000/78400000/78395600/78395505/6119f5e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Double Bed, City View | Living area](https://images.trvl-media.com/lodging/79000000/78400000/78395600/78395505/3fc53037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 14-16 Grosvenor Street Luxury Apartments Chester 6.4/10 (10) "Perfect location, great size property. Maybe a little tired in terms of furniture but overall, highly recommend." CA $126 CA $189 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chester-Hotels-14-16-Grosvenor-Street-Luxury-Apartments.h78395505.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=2025-10-15&endDate=2025-10-16®ionId=6590&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews