Title: Book the Best Ashland WINERY Hotels in 2025 | Expedia.ca [Ashland Travel Guide](https://expedia.ca/Ashland.dx6290)[Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d6290.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d6290.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.ca/Cheap-Flights-To-Ashland.d6290.Travel-Guide-Flights)[Things to do in Ashland](https://expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d6290.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.ca/Ashland.d6290.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/2827c471dbf315bcf8c417169ecc676c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Ashland, OR from CA $137 ![](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 Ashland Winery Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Ashland Winery Hotels ![Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/01670d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/52c43a54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/af89d40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Callahan's Mountain Lodge Ashland 8.8/10 Excellent (1177) "Loved our visit there, staff was top notch" CA $154 CA $178 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2acbb0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/5f7e6be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Room, Mountainside | Mountain view](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/4093c3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1571) "The hotel is exceptionally clean and very friendly!" CA $122 CA $137 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/eed498c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/9264db9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/d3116ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bard's Inn, BW Signature Collection by Best Western Historic Downtown District 8.6/10 Excellent (1003) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " CA $153 CA $170 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/7ef065ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sunrise Suite](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/887e2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Creekside Suite | Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/235e6367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657800/89657723/306c76f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Willows Inn and Estate Ashland 9.8/10 Exceptional (32) "Beautiful setting close to downtown. Pool is marvelous!" CA $271 CA $275 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ashland-Hotels-Country-Willows-Inn-And-Estate.h89657723.Hotel-Information) ![Honeymoon Suite #7, 1 Queen Bed, Jetted Tub, Mountain Views](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/965ebb54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/5496e43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/0e643dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/7283f84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peerless Hotel by WanderLodges Historic Railroad District 9.6/10 Exceptional (90) "A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown. " CA $162 CA $258 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Ashland-Hotels-The-Peerless-Hotel-By-WanderLodges.h92723926.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103030000/103028500/103028494/da2b7e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/104000000/103030000/103028500/103028494/35fe933a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103030000/103028500/103028494/8ac29521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/104000000/103030000/103028500/103028494/f1edadd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. Ashland 10/10 Exceptional (31) "This place was perfect! Very clean, great decor, and the view was amazing. We loved beginning and ending our day on the porch, enjoying the peace and quiet. The owners were great and had a very quick response time. We would definitely stay there again. Thank you for such a wonderful place for a much-needed getaway!" CA $213 CA $373 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ashland-Hotels-Siskiyou-Mountain-Place.h103028494.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/6d9845b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/4de1acfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/87a63cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room](https://images.trvl-media.com/lodging/47000000/46090000/46085100/46085022/98094857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Arden Forest Inn Ashland 9.8/10 Exceptional (100) "This was our second visit and always a nice stay during the summer months. " CA $216 CA $241 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Medford-Hotels-Arden-Forest-Inn.h46085022.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/71000000/70440000/70436800/70436753/b1b3b300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70440000/70436800/70436753/0055afe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70440000/70436800/70436753/d9a4424f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/71000000/70440000/70436800/70436753/c8c8296c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Dragon House Ashland 10/10 Exceptional (98) "We were looking for a nice quiet location close to the highway and this was perfect. It was very clean, the kitchen was beautiful and the welcome cookies were delicious. Thank you!" CA $245 CA $283 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Ashland-Hotels-1.h70436753.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111997800/111997707/w4096h2297x0y216-bffcc2c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/112000000/112000000/111997800/111997707/fbf249ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/112000000/112000000/111997800/111997707/3ecd1847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury House, Mountain View | Living area](https://images.trvl-media.com/lodging/112000000/112000000/111997800/111997707/f3007092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grandview of Ashland Ashland 10/10 Exceptional (1) "I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. " CA $425 CA $732 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Ashland-Hotels-Grandview-Of-Ashland.h111997707.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104080000/104075400/104075379/a9297270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104080000/104075400/104075379/777db126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104080000/104075400/104075379/w900h683x62y0-7a798239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/105000000/104080000/104075400/104075379/1971e0da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chateau Herbe ~ Oberon Suite w/ Kitchen Ashland 9.4/10 Exceptional (16) "Excellent place to stay. Grounds were stunning and the chateau felt cozy and private. " CA $200 CA $294 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ashland-Hotels-Oberon-Suite-In-A-Castle-Sweeping.h104075379.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=2025-10-27&endDate=2025-10-28®ionId=6290&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![Ashland Hills Hotel & Suites](//images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg) ### Ashland Hills Hotel & Suites 10/10 Excellent "The hotel is nice and the quality is almost always the same, reliable, nice amenities. The beds are comfortable. Beautiful Ashland views. There are ebbs and flows with the staff…small town, some are great and fast some are good and slow. There are roaches by the hot tub beware, only saw them outside. " [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.Hotel-Information) ![Comfort Inn & Suites Ashland](//images.trvl-media.com/lodging/1000000/10000/3500/3448/9eb7c716_y.jpg) ### Comfort Inn & Suites Ashland 10/10 Excellent "The room was clean. Front desk staff was very helpful. Checking in and out was very easy." [](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 "So first of all, the people who run the place our friendly and very helpful. We needed to make some last minute changes to our accommodations and Shasta sorted it all out for us. Great customer service. The room decor is maybe a little tired, but they have spent money where it counts. The mattresses, pillows, and bedding were incredibly comfortable. We also loved that the double room consisted of a room with a bed and a second, separate room with a bed. Great if you're traveling with kids! The fridge was sizeable and it worked great. Everything was very clean. Would absolutely stay here again. " [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.Hotel-Information) ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Nice, clean and quiet. The staff was great and they have a good breakfast. It is pet-friendly, with a small “park” in the parking lot for them." [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Plaza Inn & Suites at Ashland Creek](//images.trvl-media.com/lodging/1000000/890000/880600/880585/7e1c38a2_y.jpg) ### Plaza Inn & Suites at Ashland Creek 10/10 Excellent "With a great view of the garden, spacious room with couch and super soft bed, Tesla chargers, and a short walk to Lithia Park - this place is perfect for us! The free breakfast is pretty good too: bacon, scrambled eggs, yogurt, oranges/bananas and a waffle maker. Only a couple minor down sides: tiny bottles of shampoo etc rather than built in large bottles, plastic water glasses and a really narrow driveway down to the chargers. Nothing to change our minds, though. A great place to stay. " [](https://expedia.ca/Medford-Hotels-Plaza-Inn-Suites-At-Ashland-Creek.h880585.Hotel-Information) ![The Bard's Inn, BW Signature Collection by Best Western](//images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6_y.jpg) ### The Bard's Inn, BW Signature Collection by Best Western 10/10 Excellent "Clean room. Great location. Friendly staff" [](https://expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Lithia Springs Resort](//images.trvl-media.com/lodging/1000000/900000/893600/893586/a941912b_y.jpg) ### Lithia Springs Resort 10/10 Excellent "We enjoyed a quiet stay in one of the suites. The staff were friendly and helpful. The beds were very comfortable and everything was clean. We had fun walking around the grounds and seeing a group of wild turkeys wander past. " [](https://expedia.ca/Medford-Hotels-Lithia-Springs-Resort.h893586.Hotel-Information) ![Holiday Inn Express & Suites Ashland by IHG](//images.trvl-media.com/lodging/1000000/850000/845500/845432/2a6193b5_y.jpg) ### Holiday Inn Express & Suites Ashland by IHG 10/10 Excellent "We were in need of medical care and the staff was able to provide us with information on an urgent care clinic. Our room wasn’t ready when we checked in (early) but we were notified by text when we could check back in. We didn’t have breakfast there so can’t comment on that." [](https://expedia.ca/Medford-Hotels-Holiday-Inn-Express-Suites-Ashland.h845432.Hotel-Information) ![Ashland Springs Hotel](//images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91_y.jpg) ### Ashland Springs Hotel 10/10 Excellent "Lovely hotel!" 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[Motels in Phoenix](https://www.expedia.ca/Phoenix-Motels.d6047195-aaMotels.Travel-Guide-Accommodation) - [Resorts in Phoenix](https://www.expedia.ca/Phoenix-Resort-Hotels.d6047195-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Phoenix](https://www.expedia.ca/Phoenix-Townhomes.d6047195-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near Rogue Valley Country Club](https://www.expedia.ca/Rogue-Valley-Country-Club-Hotels.0-l6078463-0.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Skidmore Academy Historic District](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels-Best-Western.0-n553248635976482103-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Skidmore Academy Historic District](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels-Pet-Friendly-Hotel.0-n553248635976482103-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Skidmore Academy Historic District Hotels](https://www.expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels.0-n553248635976482103-0.Travel-Guide-Filter-Hotels) - [Hotels near Southern Oregon University](https://www.expedia.ca/Southern-Oregon-University-Hotels.0-l6188400-0.Travel-Guide-Filter-Hotels) - [Hotels near Sumner Parker Field](https://www.expedia.ca/Sumner-Parker-Field-Airport-Hotels.0-aAHM-0.Travel-Guide-Filter-Hotels) - [Farmstay in Talent](https://www.expedia.ca/Talent-Agritourism.d6347896-aaAgritourism.Travel-Guide-Accommodation) - [Guest Houses in Talent](https://www.expedia.ca/Talent-Guest-Houses.d6347896-aaGuestHouses.Travel-Guide-Accommodation) - [Adults Only Resorts & in Talent](https://www.expedia.ca/Talent-Hotels-Adults-Only-Resorts.0-0-d6347896-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Talent](https://www.expedia.ca/Talent-Hotels-Cheap-Hotels.0-0-d6347896-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Talent](https://www.expedia.ca/Talent-Hotels-Couples-Resorts-Hotels.0-0-d6347896-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Talent](https://www.expedia.ca/Talent-Hotels-Hotels-With-Balconies.0-0-d6347896-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - 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[Flights from New York (JFK) to Ashland (AHM)](https://www.expedia.ca/lp/flights/jfk/ahm/new-york-to-ashland) - [Flights from Kuwait City (KWI) to Ashland (AHM)](https://www.expedia.ca/lp/flights/kwi/ahm/kuwait-city-to-ashland) - [Flights from Medford (MFR) to Ashland (AHM)](https://www.expedia.ca/lp/flights/mfr/ahm/medford-to-ashland) - [Flights from Minneapolis (MSP) to Ashland (AHM)](https://www.expedia.ca/lp/flights/msp/ahm/minneapolis-to-ashland) - [Flights from Oakland (OAK) to Ashland (AHM)](https://www.expedia.ca/lp/flights/oak/ahm/oakland-to-ashland) - [Flights from Ontario (ONT) to Ashland (AHM)](https://www.expedia.ca/lp/flights/ont/ahm/ontario-to-ashland) - [Flights from Portland (PDX) to Ashland (AHM)](https://www.expedia.ca/lp/flights/pdx/ahm/portland-to-ashland) - [Flights from San Diego (SAN) to Ashland (AHM)](https://www.expedia.ca/lp/flights/san/ahm/san-diego-to-ashland) - [Flights from San Antonio (SAT) to Ashland (AHM)](https://www.expedia.ca/lp/flights/sat/ahm/san-antonio-to-ashland) - 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[Visit Skidmore Academy Historic District](https://www.expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103) - [Edenvale Winery](https://www.expedia.ca/EdenVale-Winery-Medford.d6087459.Vacation-Attraction) - [Visit Medford](https://www.expedia.ca/Medford.dx602702) - [Thomas Theatre](https://www.expedia.ca/Thomas-Theatre-Historic-Downtown-District.d6078459.Vacation-Attraction) - [Car rental Talent](https://www.expedia.ca/Car-Rentals-In-Talent.d6347896.Car-Rental-Guide) - [Book Winery Hotels in Ashland on Expedia.com](https://www.expedia.com/Ashland-Hotels-Winery-Hotel.0-0-d6290-tWineryHotel.Travel-Guide-Filter-Hotels)