Title: Book the Best Oshawa WINERY Hotels in 2025 | Expedia.ca [Oshawa Travel Guide](https://expedia.ca/Oshawa.dx6057905)[Hotels in Oshawa](https://expedia.ca/Oshawa-Hotels.d6057905.Travel-Guide-Hotels)[Vacation Rentals in Oshawa](https://expedia.ca/Oshawa-Vacation-Rentals.d6057905.Travel-Guide-VacationRentals)[Flights to Oshawa](https://expedia.ca/Cheap-Flights-To-Oshawa.d6057905.Travel-Guide-Flights)[Oshawa Car Rentals](https://expedia.ca/Car-Rentals-In-Oshawa.d6057905.Car-Rental-Guide)[Oshawa Vacation Packages](https://expedia.ca/Oshawa.d6057905.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/4f6a286dfe3f07d09b8284dad6e8e911.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Oshawa from CA $212 ![](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 Oshawa Winery Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6057905&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6057905&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6057905&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6057905&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oshawa Winery Hotels ![Interior](https://images.trvl-media.com/lodging/41000000/40010000/40002400/40002365/36c92929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/41000000/40010000/40002400/40002365/a03d409e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/41000000/40010000/40002400/40002365/82984218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/41000000/40010000/40002400/40002365/6f4ad248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willow Pond Bed and Breakfast Port Perry 9.6/10 Exceptional (14) "Enjoyed my stay" CA $149 CA $216 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Scugog-Hotels-Willow-Pond-Satellite-Bed-And-Breakfast.h40002365.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103470000/103468200/103468112/da53ed27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103470000/103468200/103468112/82eacab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103470000/103468200/103468112/30ea4af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103470000/103468200/103468112/41b8a4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Winter Gateaway Nestleton Station 10/10 Exceptional (3) "It is not just a very nice place to stay, it is also an authentic and a unique experience that the host offers to his guests, especially if one opts for the Italian Dinner...Sublime! " CA $188 CA $476 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Scugog-Hotels-A-Hidden-Cozy-Gem-In-Beautiful-Scugog.h103468112.Hotel-Information) ![Sauna](https://images.trvl-media.com/lodging/107000000/106650000/106646600/106646505/w904h683x60y0-518db78b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106650000/106646600/106646505/w907h683x59y0-a1094741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/107000000/106650000/106646600/106646505/w904h683x60y0-8eb987a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/107000000/106650000/106646600/106646505/w1024h616x0y34-b25fd63a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Uxbridge Igloo on Pefferlaw Creek with Private Lake. Pet Friendly! Uxbridge 8.0/10 Very good (2) "The whole setup is very thoughtful and provides a wonderful sheltered camping experience on a private creek. " CA $144 CA $217 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Uxbridge-Hotels-The-Uxbridge-Igloo-On-Pefferlaw-Creek-With-Private-Lake-Pet-Friendly.h106646505.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69250000/69247400/69247302/8fa6d805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69250000/69247400/69247302/b04a383b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69250000/69247400/69247302/4e6a499e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69250000/69247400/69247302/de21519a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Assets Event Venue Modern interior with elegant Décor Whitby 9.2/10 Wonderful (16) "Amazing home and an even better backyard! Great for large groups as there is so much space. " CA $1,800 CA $3,097 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Whitby-Hotels-Modern-Interior-With-Intoxicated-Decor.h69247302.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/13000000/12540000/12535400/12535339/68ce661f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Suite (Second floor)](https://images.trvl-media.com/lodging/13000000/12540000/12535400/12535339/6730b9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12540000/12535400/12535339/171ab0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12540000/12535400/12535339/b52c84c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Plantation House Bed & Breakfast Port Hope 9.8/10 Exceptional (60) "Bed were extremely comfortable & food was delicious & well presented!" CA $399 CA $451 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Peterborough-Hotels-Plantation-House-Bed-Breakfast.h12535339.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76800000/76796900/76796819/786f8ed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76800000/76796900/76796819/e1f4d218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76800000/76796900/76796819/2220f64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, stovetop, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/77000000/76800000/76796900/76796819/8a662fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking Aurora 10/10 Exceptional (12) "Super clean and cozy, very comfortable bed, would definitely stay again!" CA $120 CA $212 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Toronto-Hotels-Stylish-Main-Level-Suite-With-Separate-Entrance.h76796819.Hotel-Information) ![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/102000000/101090000/101087100/101087060/30c651b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/102000000/101090000/101087100/101087060/83940062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101090000/101087100/101087060/11897d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Balcony view](https://images.trvl-media.com/lodging/102000000/101090000/101087100/101087060/be3cd05b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BightStays Downtown Toronto 7.2/10 Good (48) "Great location, clean, would recommend." CA $295 CA $484 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Toronto-Hotels-BightStays.h101087060.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. 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[Hotels & Resorts for Couples in Whitby](https://www.expedia.ca/Whitby-Hotels-Couples-Resorts-Hotels.0-0-d7606-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Family-Hotel.0-0-d7606-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Golf-Hotel.0-0-d7606-tGolfHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Historic-Hotel.0-0-d7606-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Whitby](https://www.expedia.ca/Whitby-Hotels-Honeymoon-Hotels.0-0-d7606-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotel-With-Early-Check-In.0-0-d7606-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotel-With-Pool.0-0-d7606-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotel-With-Wifi.0-0-d7606-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-A-Lazy-River.0-0-d7606-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Balconies.0-0-d7606-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Bar.0-0-d7606-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d7606-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Free-Breakfast.0-0-d7606-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Free-Parking.0-0-d7606-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Hot-Tubs.0-0-d7606-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Indoor-Pool.0-0-d7606-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Kitchenettes.0-0-d7606-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Smoking-Rooms.0-0-d7606-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Whitby](https://www.expedia.ca/Whitby-Hotels-Hotels-With-Waterslides.0-0-d7606-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-LGBT-Friendly-Hotel.0-0-d7606-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Lake Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Lake-Hotels.0-0-d7606-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Luxury-Hotel.0-0-d7606-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Mountain-Hotels.0-0-d7606-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Oceanfront-Hotels.0-0-d7606-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Pet-Friendly-Hotel.0-0-d7606-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Romantic-Hotel.0-0-d7606-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Scuba Diving Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Scuba-Diving-Vacations.0-0-d7606-tscubadivingvacations.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Shopping-Hotel.0-0-d7606-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Ski-Hotel.0-0-d7606-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Waterpark-Hotels.0-0-d7606-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Wedding-Hotels.0-0-d7606-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Whitby](https://www.expedia.ca/Whitby-Hotels-Winery-Hotel.0-0-d7606-tWineryHotel.Travel-Guide-Filter-Hotels) - [Flights to Toronto](https://www.expedia.ca/Cheap-Flights-To-Toronto.d178314.Travel-Guide-Flights)