Title: Book the Best Westside WINERY Hotels in 2025 | Expedia.ca [Vacation Rentals in Jacksonville](https://expedia.ca/Jacksonville-Vacation-Rentals.d602997.Travel-Guide-VacationRentals)[Flights to Jacksonville](https://expedia.ca/Cheap-Flights-To-Jacksonville.d602997.Travel-Guide-Flights)[Things to do in Jacksonville](https://expedia.ca/Things-To-Do-In-Jacksonville.d602997.Travel-Guide-Activities)[Westside Car Rentals](https://expedia.ca/Car-Rentals-In-Westside.d553248635976384838.Car-Rental-Guide)[Westside Vacations](https://expedia.ca/Westside.d553248635976384838.Destination-Travel-Guides) ![Empty Docks on the River](https://images.trvl-media.com/place/553248635976384838/7ab17de3-c551-480d-b6ee-ebdf76bb7df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Westside, FL - ![](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 Westside Winery Hotels Tonight [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976384838&startDate=2025-11-23&endDate=2025-11-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976384838&startDate=2025-11-24&endDate=2025-11-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976384838&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976384838&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Westside Winery Hotels ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13500/13414/bf11d2a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/13500/13414/076020e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/13500/13414/b2a26771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/13500/13414/f7d141af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Jacksonville Beach Oceanfront Jacksonville Beach 8.6/10 Excellent (1001) "Room was very nice. Front desk staff was very pleasant and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $200 CA $227 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Jacksonville-Hotels-Courtyard-By-Marriott-Jacksonville-Beach-Oceanfront.h13414.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777110/335b1fee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777110/fba2ad11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777110/865695f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/100000000/99780000/99777200/99777110/w4000h2663x0y4-b90721a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel Jacksonville St Johns Town Center Southside 9.2/10 Wonderful (160) "Staff was excellent...highly recommend this Hotel" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Robert CA $196 CA $222 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Jacksonville-Hotels-AC-Hotel-Jacksonville-ST-Johns-Town-CTR.h99777110.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57890000/57882700/57882676/b63e4a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57890000/57882700/57882676/ac73bbf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57890000/57882700/57882676/59e728cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57890000/57882700/57882676/2bf6f91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Studio Entry Palm Valley 10/10 Exceptional (88) "Everything about this stay was fantastic! Steve and Carol are absolutely warm, welcoming and wholesome. They were so helpful and kind. The place was clean and cozy and perfect for me. I would stay here again in a heart beat" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Crystal CA $176 CA $335 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Jacksonville-Hotels-Private-Studio-Entry.h57882676.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34420000/34413500/34413457/a435d2ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/35000000/34420000/34413500/34413457/36e9c181.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/35000000/34420000/34413500/34413457/dffb8ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34420000/34413500/34413457/53a748b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Jacksonville - Town Center by IHG Southside 9.6/10 Exceptional (1009) "Nice staff nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $159 CA $181 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Jacksonville-Hotels-Holiday-Inn-Express-Suites-Jacksonville-Town-Center.h34413457.Hotel-Information) ![On the beach, beach towels](https://images.trvl-media.com/lodging/58000000/57110000/57100700/57100658/49f3f285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/58000000/57110000/57100700/57100658/fb810da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57110000/57100700/57100658/e915d03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/58000000/57110000/57100700/57100658/3a94de1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront: 607 Surf Villas at Sawgrass Beach Club Near TPC & Mayo Clinic Sawgrass 10/10 Exceptional (73) "We loved this condo! It was clean and offered all the essentials we needed. Beautiful view of the ocean with a quick walk to the private beach! Quick response from the agent and the owner was easy to work with when we wanted to add an extra day. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robynn W. CA $282 CA $721 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Jacksonville-Hotels-607-Surf-Villas-Oceanfront-Condo-At-Sawgrass-Beach-Club.h57100658.Hotel-Information) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106100000/106093300/106093254/80a176ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106100000/106093300/106093254/38da52df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106100000/106093300/106093254/6e75360f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106100000/106093300/106093254/bfa28208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Oceanfront Resort w Beach access & Pool Sawgrass 9.0/10 Wonderful (2) "Perfect little studio that’s a short walk to the beach and close to TPC Sawgrass! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maddie M. CA $175 CA $642 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Jacksonville-Hotels-Perfect-Getaway-Ponte-Vedra-Beach-Lifestyle.h106093254.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68360000/68354200/68354115/1535b0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices, printers](https://images.trvl-media.com/lodging/69000000/68360000/68354200/68354115/a410982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68360000/68354200/68354115/cc64c87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68360000/68354200/68354115/a03e3f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern & Historic quiet house near Arenas|Yard|No Pet fees|R&R |Street Parking Urban Core 9.6/10 Exceptional (4) "We enjoyed our stayed. The house was very clean and in a good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeffrey a. CA $204 CA $530 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Jacksonville-Hotels-Historic-Modern-Living-In-Springfield-Near-Arena-Pets-Free-Street-Parking.h68354115.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/72000000/71490000/71486600/71486517/f0862079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71490000/71486600/71486517/7f1bd133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71490000/71486600/71486517/cd721e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71490000/71486600/71486517/5e45172e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic 🏖️ Getaway! 2 king beds! EV charger. A 10 min drive from Mayo Clinic! Jacksonville Beach 9.6/10 Exceptional (28) "Loved the location and the house was perfect. We enjoyed the outback area with the firepit. Beds were all comfortable and I would recommend staying there" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy M. CA $234 CA $612 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Jacksonville-Hotels-Few-Steps-Walk-To-Jax-Beach-2-King-Beds-W-EV-Charger-And-Private-Backyard.h71486517.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117070000/117063300/117063300/90cfbf96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117070000/117063300/117063300/2841b335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117070000/117063300/117063300/a2a44bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117070000/117063300/117063300/470dc0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Noc Nest Family Retreat - Screened Lanai - Fire table - Outdoor BBQ - Game Room Ponte Vedra 10/10 Exceptional (8) "Perfect house for our trip" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael M. CA $357 CA $881 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Jacksonville-Hotels-Noc-Nest-Family-Retreat-Screened-Lanai-Fire-Table-Outdoor-BBQ.h117063300.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112530000/112527500/112527440/bbf64eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112530000/112527500/112527440/7811f9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112530000/112527500/112527440/w2832h1893x0y0-10acc5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112530000/112527500/112527440/01a56ce3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southern Charm at Southern Rose East Arlington 10/10 Exceptional (1) "Long weekend here with no issues at all. Would book again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe S. CA $366 CA $1,119 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Jacksonville-Hotels-Southern-Charm-At-Southern-Rose.h112527440.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=2025-12-07&endDate=2025-12-08®ionId=553248635976384838&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Westside Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in Middleburg](https://www.expedia.ca/2Star-Middleburg-Hotels.s20-0-d183107.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Lakeside](https://www.expedia.ca/5Star-Lakeside-Jacksonville-Hotels.s50-n553248635975874811-0.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Amelia Island](https://www.expedia.ca/Amelia-Island-Hotels-Hotel-With-Pool.0-0-d10814-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Avondale](https://www.expedia.ca/Avondale-Jacksonville-Hotels-Beach-Hotel.0-n6341884-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Avondale](https://www.expedia.ca/Avondale-Jacksonville-Hotels-Boutique-Hotel.0-n6341884-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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[Flights from Middleburg](https://www.expedia.ca/lp/flights/183107/flights-from-middleburg) - [Flights from Gainesville (GNV) to Jacksonville (VQQ)](https://www.expedia.ca/lp/flights/gnv/vqq/gainesville-to-jacksonville) - [Flights from St. Petersburg (PIE) to Jacksonville (VQQ)](https://www.expedia.ca/lp/flights/pie/vqq/st-petersburg-to-jacksonville) - [Visit Avondale](https://www.expedia.ca/Jacksonville-Avondale.dx6341884) - [Visit Cedar Hills](https://www.expedia.ca/Jacksonville-Cedar-Hills.dx553248635976481821) - [Visit Mixon Town](https://www.expedia.ca/Jacksonville-Mixon-Town.dx553248635976477967) - [Visit Riverside](https://www.expedia.ca/Jacksonville-Riverside.dx6341888) - [Car rental Middleburg](https://www.expedia.ca/Car-Rentals-In-Middleburg.d183107.Car-Rental-Guide) - [Car rental Orange Park](https://www.expedia.ca/Car-Rentals-In-Orange-Park.d9262.Car-Rental-Guide) - [Global Rent a Car Rental Cars in Riverside](https://www.expedia.ca/Global-Rent-A-Car-Car-Rentals-In-Riverside.d6341888-c1062.Car-Rental-Guide-Suppliers) - [Book Hotels in Westside on Expedia.com](https://www.expedia.com/Westside-Jacksonville-Hotels-Winery-Hotel.0-n553248635976384838-0-tWineryHotel.Travel-Guide-Filter-Hotels)