Title: Book the Best Jacksonville WINERY Hotels in 2025 | Expedia.ca [Hotels in Jacksonville](https://expedia.ca/Jacksonville-Hotels.d119087.Travel-Guide-Hotels)[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 Car Rentals](https://expedia.ca/Car-Rentals-In-Jacksonville.d119087.Car-Rental-Guide)[Jacksonville Vacation Packages](https://expedia.ca/Jacksonville.d119087.Destination-Travel-Guides) ![Jacksonville](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/106000/106461-Jacksonville.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Jacksonville, OR from CA $146 - ![](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 Winery Hotels Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=119087&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=119087&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=119087&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=119087&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Jacksonville Winery Hotels ![32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/736bb453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/30167641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/a9f07da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/fef2d532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wine Country Inn Jacksonville 9.4/10 Exceptional (1001) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Priscilla CA $132 CA $146 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Medford-Hotels-Wine-Country-Inn.h4011768.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78113200/78113145/c338542e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78120000/78113200/78113145/f9d8e483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78120000/78113200/78113145/w907h683x59y0-4028fda3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78113200/78113145/w903h683x60y0-87ad5c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Wild West Covered Wagon next to River Grants Pass 10/10 Exceptional (6) "We had a wonderful glamping experience. The host thought of everything. Our kids were so happy and enjoyed every minute! The trails with cute painted rocks, the swimming hole, the toys, the hammock, the teepee...it was so much fun! Thank you, we'll be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chandry B. CA $112 CA $206 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Jacksonville-Hotels-Cozy-Wild-West-Covered-Wagon-Next-To-River.h78113145.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/8a4ca45e.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) ![Standard King Room](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/7e445210.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) ### Magnolia Hotel Jacksonville Historic District 9.0/10 Wonderful (775) "Great place for concerts at the Britt. Quiet and clean with a great atmosphere. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $216 CA $238 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Jacksonvilles-Magnolia-Inn.h1798022.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90950000/90942100/90942099/w904h683x59y0-fe9c0316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90950000/90942100/90942099/w909h683x58y0-2ebf6461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90950000/90942100/90942099/c6df3c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90950000/90942100/90942099/w905h683x60y0-f8f339a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville Jacksonville 9.8/10 Exceptional (32) "The cottage was the perfect little place to retreat after wine tasting and walking around Jacksonville. Just far enough out and amongst wineries but still close to downtown :) lovely outdoor space with a relaxing river front seating. We just loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelseyann R. CA $168 CA $306 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Jacksonville-Hotels-Vrbo-Property.h90942099.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) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/dd03e2fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/109000000/108160000/108156900/108156836/c27de03c.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 Suite Upstairs - 2 blocks Historic Downtown J'ville Jacksonville Historic District 9.8/10 Exceptional (7) "The room was open and spacious, nicely decorated, welcoming and comfortable. It was also within walking distance from the concert I came to attend locally!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl CA $171 CA $319 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Jacksonville-Hotels-Cowgirl-Craftsman-Private-Suite-Upstairs-2-Blocks-Historic-Downtown-Jville.h108156836.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/96000000/95310000/95304400/95304355/66fe202d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/96000000/95310000/95304400/95304355/277978dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95310000/95304400/95304355/618b2c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95310000/95304400/95304355/0c611182.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \-River Retreat Log Cabin w/ Gym, Game Room, and Sauna- Jacksonville 10/10 Exceptional (2) "What a great slice of heaven! The home was great and the surrounding property was beautiful. We will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim F. CA $268 CA $749 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Jacksonville-Hotels-River-Retreat-Log-Cabin-W-Gym.h95304355.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/104000000/103100000/103092400/103092308/a5363fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103100000/103092400/103092308/71830842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite | Living area](https://images.trvl-media.com/lodging/104000000/103100000/103092400/103092308/dca7ea0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/104000000/103100000/103092400/103092308/8c3f684a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Orth House Inn by Remotion Jacksonville 9.4/10 Exceptional (21) "It was a lovely stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $202 CA $293 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Jacksonville-Hotels-The-Orth-House-Inn-By-Remotion.h103092308.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39200000/39192200/39192112/933addb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39200000/39192200/39192112/6eb203a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39200000/39192200/39192112/9bcd7921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/40000000/39200000/39192200/39192112/f95de048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charleen's Cottage~Couple Perfect!Great Location! A Gem! Jacksonville 9.8/10 Exceptional (178) "Wonderful hosts! Quiet, comfortable and clean place. Will definitely stay again when we are in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea P. CA $105 CA $147 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Jacksonville-Hotels-Charleens-Cottage-Excellent-Location-Perfect-For-A-Couple.h39192112.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/90037610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/425fb33f.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) ![Living area](https://images.trvl-media.com/lodging/120000000/119700000/119691400/119691394/9ebf8c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville Jacksonville Historic District 10/10 Exceptional (1) "The location was amazing: within walking distance of almost all the Jacksonville restaurants, stores, residential areas and the Britt Festival. The cottage was very cleaned and well-maintained. Ashley was very responsive and helpful in making all the arrangements for our party." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana S. CA $188 CA $503 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Jacksonville-Hotels-The-Williams-Luxe-2-Bedroom-Cottage-Wonsite-Parking-In-Downtown-Jacksonville.h119691394.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101900000/101899500/101899433/w907h683x58y0-c7b4f93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101900000/101899500/101899433/w922h682x51y0-dba72ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101900000/101899500/101899433/w924h683x50y0-4d32aa17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101899500/101899433/w918h683x47y0-4e730aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Barn in Wine Country Jacksonville 9.6/10 Exceptional (8) "This was a great place to stay. Loved the animals and river access for fishing and swimming. Winery next door was a plus too. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth J. CA $238 CA $394 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Jacksonville-Hotels-Red-Barn-In-Wine-Country.h101899433.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=2025-11-16&endDate=2025-11-17®ionId=119087&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Jacksonville Hotel Reviews ![Comfort Inn & Suites Ashland](//images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716_y.jpg) ### Comfort Inn & Suites Ashland 10/10 Excellent "Clean and great space in the room" [](https://expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![Flagship Inn of Ashland](//images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1_y.jpg) ### Flagship Inn of Ashland 10/10 Excellent "Friendly staff and clean room" [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Rogue Regency Inn and Suites](//images.trvl-media.com/lodging/1000000/20000/19800/19703/8b20e842_y.jpg) ### Rogue Regency Inn and Suites 10/10 Excellent "Courteous staff. Clean room. Breakfast could use some other options, but was ok." [](https://expedia.ca/Medford-Hotels-Rogue-Regency-Inn-And-Suites.h19703.Hotel-Information) ![Clarion Pointe Medford](//images.trvl-media.com/lodging/1000000/220000/218700/218641/6a918f34_y.jpg) ### Clarion Pointe Medford 10/10 Excellent "Very courteous dront desk and very clean room with comfortable king bed" [](https://expedia.ca/Medford-Hotels-Clarion-Pointe.h218641.Hotel-Information) ![Super 8 by Wyndham Central Pt Medford](//images.trvl-media.com/lodging/2000000/1290000/1281700/1281623/fe5b1b5b_y.jpg) ### Super 8 by Wyndham Central Pt Medford 10/10 Excellent "Clean and quiet room." [](https://expedia.ca/Medford-Hotels-Super-8-By-Wyndham-Central-Pt-Medford.h1281623.Hotel-Information) ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Staff was very helpful and cheerful. Older property, but well kept up. Very convenient location right in the middle of Ashland. " [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Motel 6 Medford, OR - North](//images.trvl-media.com/lodging/1000000/1000000/996400/996397/4a6c43ed_y.jpg) ### Motel 6 Medford, OR - North 10/10 Excellent "great stay" [](https://expedia.ca/Medford-Hotels-Motel-6-Medford.h996397.Hotel-Information) ![Ashland Hills Hotel & Suites](//images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg) ### Ashland Hills Hotel & Suites 10/10 Excellent "This hotel is an expansive, beautiful propert. I would recommend for any kind of traveler. The hottub was an extra bonus." [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Motel 6 Medford, OR](//images.trvl-media.com/lodging/1000000/1000000/996200/996127/7ef01fa3_y.jpg) ### Motel 6 Medford, OR 10/10 Excellent "Had to stay here for a night while we drove person up front was super friendly and fast with checking us in and really convenient." 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[Flights to Central Point](https://www.expedia.ca/Cheap-Flights-To-Central-Point.d602408.Travel-Guide-Flights) - [Flights to Medford](https://www.expedia.ca/Cheap-Flights-To-Medford.d602702.Travel-Guide-Flights) - [Flights from Central Point](https://www.expedia.ca/lp/flights/602408/flights-from-central-point) - [Flights from Medford](https://www.expedia.ca/lp/flights/602702/flights-from-medford) - [Flights from Bellingham (BLI) to Medford (MFR)](https://www.expedia.ca/lp/flights/bli/mfr/bellingham-to-medford) - [Flights from Buffalo (BUF) to Medford (MFR)](https://www.expedia.ca/lp/flights/buf/mfr/buffalo-to-medford) - [Flights from Detroit (DTW) to Medford (MFR)](https://www.expedia.ca/lp/flights/dtw/mfr/detroit-to-medford) - [Flights from Meridian (MEI) to Medford (MFR)](https://www.expedia.ca/lp/flights/mei/mfr/meridian-to-medford) - [Flights from Portland (PDX) to Medford (MFR)](https://www.expedia.ca/lp/flights/pdx/mfr/portland-to-medford) - [Flights from Reno (RNO) to Medford (MFR)](https://www.expedia.ca/lp/flights/rno/mfr/reno-to-medford) - 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[Flights from Saskatoon (YXE) to Medford (MFR)](https://www.expedia.ca/lp/flights/yxe/mfr/saskatoon-to-medford) - [Flights from Abbotsford (YXX) to Medford (MFR)](https://www.expedia.ca/lp/flights/yxx/mfr/abbotsford-to-medford) - [Flights from Calgary (YYC) to Medford (MFR)](https://www.expedia.ca/lp/flights/yyc/mfr/calgary-to-medford) - [Flights from Victoria (YYJ) to Medford (MFR)](https://www.expedia.ca/lp/flights/yyj/mfr/victoria-to-medford) - [Flights from Toronto (YYZ) to Medford (MFR)](https://www.expedia.ca/lp/flights/yyz/mfr/toronto-to-medford) - [Visit Central Point](https://www.expedia.ca/Central-Point.dx602408) - [Visit City Center Medford](https://www.expedia.ca/Medford-City-Center-Medford.dx6189484) - [Medford Vacations](https://www.expedia.ca/Medford.d602702.Destination-Travel-Guides) - [Visit Medford](https://www.expedia.ca/Medford.dx602702) - [Alamo Rent A Car Rental Cars in Medford](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Medford.d602702-c6.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Medford](https://www.expedia.ca/Budget-Car-Rentals-In-Medford.d602702-c39.Car-Rental-Guide-Suppliers) - [Car rental Medford](https://www.expedia.ca/Car-Rentals-In-Medford.d602702.Car-Rental-Guide) - [Rental cars Rogue Valley Intl. airport](https://www.expedia.ca/Car-Rentals-In-Rogue-Valley-Intl.d6030025.Car-Rental-Guide) - [Car rentals near The Expo](https://www.expedia.ca/Car-Rentals-In-The-Expo.d6189462.Car-Rental-Guide) - [Express Travel Group Rental Cars in Medford](https://www.expedia.ca/Express-Travel-Group-Car-Rentals-In-Medford.d602702-c1124.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Medford](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Medford.d602702-c33.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Medford](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Medford.d602702-c45.Car-Rental-Guide-Suppliers) - [Medford Vacation Rentals](https://www.expedia.ca/Medford-Vacation-Rentals.d602702.Travel-Guide-VacationRentals) - [Things to do in Central Point](https://www.expedia.ca/Things-To-Do-In-Central-Point.d602408.Travel-Guide-Activities) - [Things to do in Jackson County](https://www.expedia.ca/Things-To-Do-In-Jackson-County.d553248635976431789.Travel-Guide-Activities) - [Book Winery Hotels in Jacksonville on Expedia.com](https://www.expedia.com/Jacksonville-Hotels-Winery-Hotel.0-0-d119087-tWineryHotel.Travel-Guide-Filter-Hotels)