Title: Book the Best Historic Downtown District WINERY Hotels in 2025 | Expedia.ca [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)[Historic Downtown District Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Downtown-District.d553248635976471666.Car-Rental-Guide)[Historic Downtown District Vacations](https://expedia.ca/Historic-Downtown-District.d553248635976471666.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/2827c471dbf315bcf8c417169ecc676c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Historic Downtown District, OR from CA $92 - ![](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 Historic Downtown District Winery Hotels Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&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=553248635976471666&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Historic Downtown District Winery Hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/7fe2e00a.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 (1009) "Great location close to everything!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kari CA $139 CA $155 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/7ace6696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/5284c096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/71f81a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/7cb6fc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Medford-Central Point by IHG Central Point 9.0/10 Wonderful (1001) "Everything was excellent, thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon CA $149 CA $167 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Hotel-Suites-Medford-Central-Point.h1573382.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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/7b9348b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratford Inn Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1569) "We had a very nice stay! Rooms were comfortable, and the location is great - many great dining choices and entertainment within walking distance of the hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $126 CA $141 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/8b20e842.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/eebd3461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair salon](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/ea36dd0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/63c12e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rogue Regency Inn and Suites Medford 9.0/10 Wonderful (2558) "We always choose this hotel when visiting. Rooms are clean, beds are comfy, staff is friendly and the breakfast was excellent!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) janet CA $135 CA $151 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-Rogue-Regency-Inn-And-Suites.h19703.Hotel-Information) ![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) ![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) ![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) ![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) ### Callahan's Mountain Lodge Ashland 8.8/10 Excellent (1169) "Loved our visit there, staff was top notch" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $147 CA $171 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![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) ![Garden](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/fef2d532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/45fa2e41.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) ### 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) ![Reception](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/b7be0ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/3521d653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/1fc2d2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/2f76930a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Compass by Margaritaville in Medford Medford 9.6/10 Exceptional (1031) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shasta [](https://www.expedia.ca/Medford-Hotels-Compass-By-Margaritaville-In-Medford.h76138485.Hotel-Information) ![Glamp Cottage Trailer | Living area](https://images.trvl-media.com/lodging/105000000/104010000/104007600/104007590/e5ae938e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104010000/104007600/104007590/964ed6b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/105000000/104010000/104007600/104007590/a8dd4f03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Glamp Cottage Trailer](https://images.trvl-media.com/lodging/105000000/104010000/104007600/104007590/891dc776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paschal Winery Talent 9.6/10 Exceptional (13) "It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heidi CA $110 CA $245 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Talent-Hotels-Paschal-Winery.h104007590.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/1fa7d33b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/c52562e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Modern King Room Non-Smoking ( NO PETS ALLOWED )](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/46c19682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/3d717efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### City Center Motel City Center Medford 8.8/10 Excellent (446) "This is my third stay over the last couple of years. Inplan to return " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tylan CA $81 CA $92 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Medford-Hotels-City-Center-Motel-Medford-Downtown.h10357209.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) ![Interior detail](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/7283f84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/91792c28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peerless Hotel by WanderLodges Historic Railroad District 9.6/10 Exceptional (91) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew [](https://www.expedia.ca/Ashland-Hotels-The-Peerless-Hotel-By-WanderLodges.h92723926.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=2025-11-15&endDate=2025-11-16®ionId=553248635976471666&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown District 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) ![Quality Inn & Suites Medford Airport](//images.trvl-media.com/lodging/1000000/30000/28200/28140/5667147f_y.jpg) ### Quality Inn & Suites Medford Airport 10/10 Excellent "Wonderful location and convenient for the airport" [](https://expedia.ca/Medford-Hotels-Quality-Inn-And-Suites-Airport.h28140.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [3 Star Hotels in Ashland](https://www.expedia.ca/3Star-Ashland-Hotels.s30-0-d6290.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Ashland](https://www.expedia.ca/4Star-Ashland-Hotels.s40-0-d6290.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Ashland](https://www.expedia.ca/5Star-Ashland-Hotels.s50-0-d6290.Travel-Guide-Filter-Hotels) - [Hotels near Allen Elizabethan Theatre](https://www.expedia.ca/Allen-Elizabethan-Theatre-Hotels.0-l6078449-0.Travel-Guide-Filter-Hotels) - 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