Title: Book the Best St. Augustine Historic District WINERY Hotels in 2025 | Expedia.ca [St. Augustine Historic District Travel Guide](https://expedia.ca/St-Augustine-St-Augustine-Historic-District.dx6339215)[Vacation Rentals in St. Augustine](https://expedia.ca/St-Augustine-Vacation-Rentals.d6047864.Travel-Guide-VacationRentals)[Flights to St. Augustine](https://expedia.ca/Cheap-Flights-To-St-Augustine.d6047864.Travel-Guide-Flights)[Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities)[St. Augustine Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-St-Augustine-Historic-District.d6339215.Car-Rental-Guide)[St. Augustine Historic District Vacations](https://expedia.ca/St-Augustine-Historic-District.d6339215.Destination-Travel-Guides) ![Cathedral Basilica of St. Augustine showing signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/109000/109477-Basilica-Cathedral.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in St. Augustine Historic District, FL from CA $209 ![](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 St. Augustine Historic District Winery Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6339215&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=6339215&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=6339215&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=6339215&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top St. Augustine Historic District Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/12976fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/affccb1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/1000000/330000/329700/329630/adf8ee4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Monica Resort & Spa, Autograph Collection St. Augustine Historic District 9.0/10 Wonderful (1008) "Amazing Stay!" CA $312 CA $383 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/St-Augustine-Hotels-Casa-Monica-Resort-Spa.h329630.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/ccfc348c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sapphire Room - Standard Room (Adults 21+ Only)](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/8e385f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/da1d031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed | Private kitchenette](https://images.trvl-media.com/lodging/3000000/2350000/2345700/2345615/f71702d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carriage Way Inn St. Augustine Historic District 9.8/10 Exceptional (629) "Wonderful stay!" CA $275 CA $307 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/St-Augustine-Hotels-Carriage-Way-Bed-Breakfast.h2345615.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/1c8f09af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/00bca5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Hot Tub ( (3, 4, 7))](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/0bb3946f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17750000/17749000/17748908/d8b16b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Agustin Inn St. Augustine Historic District 9.4/10 Exceptional (1002) "Great staff ideal location " CA $175 CA $209 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Augustine-Hotels-Agustin-Inn.h17748908.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/35b39f5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View (Patricia's Suite)](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/7614fda5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/6c3369bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed with Sofa bed, City View (Cadiz Suite) | Living area](https://images.trvl-media.com/lodging/1000000/900000/898900/898873/d1af9b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Victorian House Bed & Breakfast St. Augustine Historic District 9.4/10 Exceptional (559) " Beautiful property fantastic breakfast and nice staff" CA $212 CA $236 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/St-Augustine-Hotels-Victorian-House.h898873.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/e0f1a250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/2b123828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/ac28c793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Country French #7 | Balcony](https://images.trvl-media.com/lodging/37000000/36690000/36682700/36682652/d4724c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kenwood Inn St. Augustine Historic District 9.6/10 Exceptional (315) "well managed clean beautiful relaxing staff was excellent close to everything " [](https://www.expedia.ca/St-Augustine-Hotels-The-Kenwood-Inn.h36682652.Hotel-Information) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956187/71e15a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956187/6b64f562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956187/567183d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956187/7d4e0c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1880 Victorian In Heart of Downtown St. Augustine Historic District 9.6/10 Exceptional (146) "Amazing property in the heart of historic downtown. " CA $95 CA $220 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Augustine-Hotels-1880-Victorian-In-Heart-Of-Downtown.h18956187.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119333900/119333866/137e2ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119340000/119333900/119333866/8da5b104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119340000/119333900/119333866/9dbbc034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119333900/119333866/80996e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Remodel, Epicenter of Historic Downtown, Balcony with Water View, Walk Everywhere, Parking St. Augustine Historic District 10/10 Exceptional (1) "This is an amazing place! Right in the heart of St. Augustine. You do have a water view from the balcony and you can see the Columbia restaurant from the other view. You can wake up and have an amazing waffle from the place directly below you! Casa Maya restaurant is litteraly 20 steps from this place and has amazing food and wonderful drinks! This place is wonderful to stay in and has been redone very well." CA $246 CA $713 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Augustine-Hotels-Brand-New-Remodel.h119333866.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/4047bae2.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/91000000/90800000/90795800/90795726/3396c695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/53247f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90800000/90795800/90795726/325e3f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heart of Historic District! Rooftop with Fire Pit, Park and Walk Everywhere, $300 in Free Tickets! St. Augustine Historic District 10/10 Exceptional (82) "Great location, nicely appointed, & comfortable!" CA $168 CA $591 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/St-Augustine-Hotels-Rooftop-WFirepit.h90795726.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/9528789e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/9e231874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/c3020d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112950000/112947200/112947161/ccc8d29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heart of Historic Downtown, Renovated, Park and Walk to Attractions, Balcony, $300 in Free Tickets! St. Augustine Historic District 10/10 Exceptional (6) "Property was well listed and described. In the heart of the historic district and in walking distance to all main tourist sites. Very clean and well stocked. As stated, there are restaurants and bars that are open and play music until midnight on the weekend so it can be loud until then. Overall an amazing place to stay!" CA $322 CA $791 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Augustine-Hotels-Heart-Of-Historic-Downtown.h112947161.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57290000/57282700/57282639/6e464bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57290000/57282700/57282639/f878a43a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/58000000/57290000/57282700/57282639/fcfa290f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57290000/57282700/57282639/273b58c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Center of Historic City- Balcony Overlooks Shops, Restaurants, Bars, Free Parking, Walk Everywhere!! St. Augustine Historic District 10/10 Exceptional (154) "Excellent property location. Relaxing and will definitely stay again!!" CA $242 CA $717 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Augustine-Hotels-New-Center-Of-Historic-City-Balcony-Overlooks-Shops.h57282639.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=2025-10-26&endDate=2025-10-27®ionId=6339215&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top St. Augustine Historic District Hotel Reviews ![Casa Monica Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/1000000/330000/329700/329630/186cf1c7_y.jpg) ### Casa Monica Resort & Spa, Autograph Collection 10/10 Excellent "This hotel is centrally located and we had an awesome experience. 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