Title: Book the Best Jacksonville Historic District WINERY Hotels in 2026 | Expedia.ca [Jacksonville Historic District Travel Guide](https://expedia.ca/Jacksonville-Jacksonville-Historic-District.dx6347523)[Vacation Rentals in Jacksonville](https://expedia.ca/Jacksonville-Vacation-Rentals.d119087.Travel-Guide-VacationRentals)[Flights to Jacksonville](https://expedia.ca/Cheap-Flights-To-Jacksonville.d119087.Travel-Guide-Flights)[Jacksonville Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Jacksonville-Historic-District.d6347523.Car-Rental-Guide)[Jacksonville Historic District Vacations](https://expedia.ca/Jacksonville-Historic-District.d6347523.Destination-Travel-Guides) ![The towns theme of swags of incense Pine makes for a festive holiday town to put on your itinerary.](https://images.trvl-media.com/place/119087/87260e65-a7db-4bf8-a018-2dd291a4e472.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Shannon Willitts ![](https://images.trvl-media.com/place/119087/87260e65-a7db-4bf8-a018-2dd291a4e472.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 Jacksonville Historic District Winery Hotels Tonight [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=6347523&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=6347523&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6347523&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=6347523&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Jacksonville Historic District hotels with winery ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/8f95829c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/4f350342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/b2c83847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/a26a95c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magnolia Hotel [](https://www.expedia.ca/Medford-Hotels-Jacksonvilles-Magnolia-Inn.h1798022.Hotel-Information) Jacksonville Historic District 9.0/10 Wonderful (778 reviews) "We loved our stay! What a great location and beautifully decorated for the holidays. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kathleen CA $208 CA $230 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Medford-Hotels-Jacksonvilles-Magnolia-Inn.h1798022.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/9ebf8c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/90037610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/7999c99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/94d36f4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville [](https://www.expedia.ca/Jacksonville-Hotels-The-Williams-Luxe-2-Bedroom-Cottage-Wonsite-Parking-In-Downtown-Jacksonville.h119691394.Hotel-Information) Jacksonville Historic District 10/10 Exceptional (2 reviews) "Wonderful place and great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) darren t. CA $201 CA $509 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Jacksonville-Hotels-The-Williams-Luxe-2-Bedroom-Cottage-Wonsite-Parking-In-Downtown-Jacksonville.h119691394.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/77f797af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/179be120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/c69262cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/386ccf58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT [](https://www.expedia.ca/Jacksonville-Hotels-Lily-Pad-1-BEST-LOCATION.h34274911.Hotel-Information) Jacksonville Historic District 10/10 Exceptional (47 reviews) "This place was awesome. Perfect location for walking to restaurants and Britt. The whole place was very clean. Looking forward to staying again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen H. CA $194 CA $414 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Jacksonville-Hotels-Lily-Pad-1-BEST-LOCATION.h34274911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/c584e522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/d2507caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/33c478e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/0bb61016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville [](https://www.expedia.ca/Jacksonville-Hotels-Cowgirl-Craftsman-Private-Suite-Upstairs-2-Blocks-Historic-Downtown-Jville.h108156836.Hotel-Information) Jacksonville Historic District 9.8/10 Exceptional (7 reviews) "Cozy, warm, and inviting stay here for an anniversary getaway. Lots of things in walking distance. Wonderful hostess and wonderful stay. We would definitely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristi CA $165 CA $308 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-Cowgirl-Craftsman-Private-Suite-Upstairs-2-Blocks-Historic-Downtown-Jville.h108156836.Hotel-Information) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/67000000/66790000/66790000/66789930/6829b836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66790000/66790000/66789930/ee3f33fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66790000/66790000/66789930/6a95fa93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/67000000/66790000/66790000/66789930/f92ab8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### California Cottage: Downtown! [](https://www.expedia.ca/Jacksonville-Hotels-California-Cottage-Downtown.h66789930.Hotel-Information) Jacksonville Historic District 9.8/10 Exceptional (42 reviews) "Love the house and location! It exceeded our expectations. Just steps away from the quaint Jacksonville downtown area. Also, quick and easy drive to Ashland. We'll definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen B. CA $160 CA $327 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-California-Cottage-Downtown.h66789930.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742171/ec3bb54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742171/c9f59086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742171/ad11af89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742171/9da76ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boutique 1 BR King Suite in historic Jacksonville. Walk to Britt Festival and wine tasting! Features a luxurious tub, comfortable king bed, and charming Inn details. Ideal for couples [](https://www.expedia.ca/Jacksonville-Hotels-King-Suite-At-The-Jacksonville-Inn-Features-Luxurious-Soaking-Tub-In-Room.h95742171.Hotel-Information) Jacksonville Historic District 10/10 Exceptional (1 review) "This is the best bed I have slept on at any vrbo. The details and tub are exquisite." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ashley b. CA $275 CA $366 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-King-Suite-At-The-Jacksonville-Inn-Features-Luxurious-Soaking-Tub-In-Room.h95742171.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742183/7effd65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742183/4819bad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742183/e1cfc9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742183/9a35e0aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacksonville Inn Room #5: Luxurious 1 BR King Guest Room. Walkable to the Britt Festival, downtown shops, and wine tasting rooms. Experience historic charm with modern comfort! [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742183.Hotel-Information) Jacksonville Historic District 9.0/10 Wonderful (2 reviews) "Very clean and comfortable. Could not ask for a better location. Had a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy S. CA $261 CA $349 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742183.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/100000000/99480000/99476900/99476853/2dda0ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99480000/99476900/99476853/36008ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99476900/99476853/3276e15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99480000/99476900/99476853/705e5e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station House Suite A [](https://www.expedia.ca/Jacksonville-Hotels-Station-House-Suite-A.h99476853.Hotel-Information) Jacksonville Historic District 9.8/10 Exceptional (23 reviews) "Beautiful & comfortable place to stay in an excellent location. Thank you for the great memories, can’t wait to stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $234 CA $592 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Jacksonville-Hotels-Station-House-Suite-A.h99476853.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742191/2cdba0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742191/1e2060d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742191/06e92e40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742191/1a105adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacksonville Inn Room #8: King Suite. Prime downtown location for festivals and dining. Comfortable king bed, Nespresso coffee, and historic boutique elegance [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742191.Hotel-Information) Jacksonville Historic District 10/10 Exceptional (3 reviews) "Rooms was spotless, and nice amenities. Such a lovely stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale CA $261 CA $349 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742191.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742187/f0d9a989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742187/8c5d42b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742187/5c474506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95750000/95742200/95742187/79aa61a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boutique 1 BR King Guest Room in historic Jacksonville, OR. Features a plush King bed, Nespresso machine, and charming Inn details. Perfect for a comfortable, walkable downtown escape. [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742187.Hotel-Information) Jacksonville Historic District 9.0/10 Wonderful (2 reviews) "Wonderful beautiful property! Will return" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $261 CA $349 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Jacksonville-Hotels-King-Guest-Room-At-The-Jacksonville-Inn.h95742187.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=2026-02-12&endDate=2026-02-13®ionId=6347523&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Jacksonville Historic District Hotel Reviews ![Rogue Regency Inn and Suites](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/8b20e842_y.jpg) ### Rogue Regency Inn and Suites 10/10 Excellent "Front desk was exceptional. Great stay." [](https://expedia.ca/Medford-Hotels-Rogue-Regency-Inn-And-Suites.h19703.Hotel-Information) ![Motel 6 Medford, OR - North](https://images.trvl-media.com/lodging/1000000/1000000/996400/996397/4a6c43ed_y.jpg) ### Motel 6 Medford, OR - North 10/10 Excellent "Room clean, front desk host was efficient and polite. Been here before, why I came back. " [](https://expedia.ca/Medford-Hotels-Motel-6-Medford.h996397.Hotel-Information) ![Stratford Inn](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Great staff, very clean, amazing location! This is a really fun place to stay in Ashland. And great year round indoor pool!" [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Holiday Inn Express Hotel & Suites Medford-Central Point by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/7ace6696_y.jpg) ### Holiday Inn Express Hotel & Suites Medford-Central Point by IHG 10/10 Excellent "Yes, it was a clean room, great amenities andcfront desk personal were wonderful. " [](https://expedia.ca/Medford-Hotels-Holiday-Inn-Express-Hotel-Suites-Medford-Central-Point.h1573382.Hotel-Information) ![Ashland Springs Hotel](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91_y.jpg) ### Ashland Springs Hotel 10/10 Excellent "Bed and pillows were absolutely amazing, super comfortable. Room stayed very warm for the cold night. Great location and super friendly staff. Getting to the parking lot prior to checking in is slightly confusing but there is a parking lot right next to it to park momentarily before moving it to the hotel’s parking lot. We would love to come back and stay here again. " [](https://expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Lithia Springs Resort](https://images.trvl-media.com/lodging/1000000/900000/893600/893586/a941912b_y.jpg) ### Lithia Springs Resort 10/10 Excellent "I love this place! One of my favorite hotels!! " [](https://expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.Hotel-Information) ![Super 8 by Wyndham Central Pt Medford](https://images.trvl-media.com/lodging/2000000/1290000/1281700/1281623/fe5b1b5b_y.jpg) ### Super 8 by Wyndham Central Pt Medford 10/10 Excellent "UPSCALE FOR THE PRICE" [](https://expedia.ca/Medford-Hotels-Super-8-By-Wyndham-Central-Pt-Medford.h1281623.Hotel-Information) ![Comfort Inn & Suites Ashland](https://images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716_y.jpg) ### Comfort Inn & Suites Ashland 10/10 Excellent "Room was spotless, great breakfast and super friendly staff!!!" [](https://expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![Ashland Hills Hotel & Suites](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg) ### Ashland Hills Hotel & Suites 10/10 Excellent "Clean room, front desk service, and Luna Cafe, was geeat." 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