Title: Book the Best Historic Downtown WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in Ocala](https://expedia.ca/Ocala-Vacation-Rentals.d6190293.Travel-Guide-VacationRentals)[Flights to Ocala](https://expedia.ca/Cheap-Flights-To-Ocala.d6190293.Travel-Guide-Flights)[Historic Downtown Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Downtown.d553248635976659158.Car-Rental-Guide)[Historic Downtown Vacations](https://expedia.ca/Historic-Downtown.d553248635976659158.Destination-Travel-Guides) ![Ocala, FL](https://images.trvl-media.com/place/553248635976659158/2d0249ed-18e3-4820-9e94-7584c69b1480.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635976659158/2d0249ed-18e3-4820-9e94-7584c69b1480.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Historic Downtown Winery Hotels Tonight [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976659158&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976659158&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976659158&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976659158&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Historic Downtown hotels with winery ![Exterior](https://images.trvl-media.com/lodging/11000000/10260000/10253700/10253641/aa72bd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/11000000/10260000/10253700/10253641/a6a0cbc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10260000/10253700/10253641/97b459b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10260000/10253700/10253641/f29e029e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shamrock Cove Inn [](https://www.expedia.ca/Ocala-Hotels-Shamrock-Historic-Inn.h10253641.Hotel-Information) Historic Downtown 8.6/10 Excellent (902 reviews) "Always a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Ocala-Hotels-Shamrock-Historic-Inn.h10253641.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27150000/27149100/27149092/24df5430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/28000000/27150000/27149100/27149092/b51c778a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible (Mobility, Accessible Tub)](https://images.trvl-media.com/lodging/28000000/27150000/27149100/27149092/cd0ee8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27150000/27149100/27149092/45a4fa0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Ocala by IHG [](https://www.expedia.ca/Ocala-Hotels-Holiday-Inn-Express-Suites-Ocala.h27149092.Hotel-Information) Ocala 9.2/10 Wonderful (1,000 reviews) "Staff was very friendly and the room was super clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tomas CA $177 CA $197 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Ocala-Hotels-Holiday-Inn-Express-Suites-Ocala.h27149092.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114170000/114165300/114165251/98b924ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114170000/114165300/114165251/4e362949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114170000/114165300/114165251/c0d5ff42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114170000/114165300/114165251/3ac89a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Ranch Retreat Near WEC, Downtown Ocala & Silver Springs [](https://www.expedia.ca/Ocala-Hotels-The-Ocala-Modern-Ranch-Retreat.h114165251.Hotel-Information) Ocala 9.6/10 Exceptional (10 reviews) "Very cozy home with all the small details covered. Owner is quick and precise with communication. Close to Rainbow Springs which was a relaxing experience. Would definitely stay at this property again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry C. [](https://www.expedia.ca/Ocala-Hotels-The-Ocala-Modern-Ranch-Retreat.h114165251.Hotel-Information) ![Smart TV, stereo](https://images.trvl-media.com/lodging/107000000/106950000/106949600/106949570/df289d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106950000/106949600/106949570/9147efd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106950000/106949600/106949570/0b1f4d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106950000/106949600/106949570/f725fb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy house with 1 bedroom and WiFi, AC, Huge Pool, 1 Acre Property Gym, Jacuzzi [](https://www.expedia.ca/Ocala-Hotels-Cozy-Cottage-With-1-Bedroom-And-WiFi.h106949570.Hotel-Information) Fort King District 6.0/10 (1 review) "The listing indicated the rental was a house. However it is almost a studio apartment attached to a house.The space itself was clean and convenient for my overnight stay. Future renters should be aware there are dogs on the property that are quite vocal and the refrigerator is dorm sized but cold." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine G. CA $203 CA $295 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Ocala-Hotels-Cozy-Cottage-With-1-Bedroom-And-WiFi.h106949570.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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