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 $100 ![](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 [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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) ## 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) ![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) ![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 (1007) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lindsey CA $139 CA $155 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.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) ![Hair salon](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/ea36dd0a.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) ![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 (2540) "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 $134 CA $151 total includes taxes & fees Oct 28 - Oct 29 [](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) ![Outdoor wedding area](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/609741f8.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 (1174) "Loved our visit there, staff was top notch" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $145 CA $169 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.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) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1580000/1573400/1573382/b4c1b610.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) ![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) ### Holiday Inn Express Hotel & Suites Medford-Central Point by IHG Central Point 9.0/10 Wonderful (1002) "Everything was excellent, thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon CA $150 CA $168 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Medford-Hotels-Holiday-Inn-Express-Hotel-Suites-Medford-Central-Point.h1573382.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) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/1d738efd.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) ![Lobby](https://images.trvl-media.com/lodging/11000000/10360000/10357300/10357209/c52562e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### City Center Motel City Center Medford 8.8/10 Excellent (446) "Great place, quaint and friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $88 CA $100 total includes taxes & fees Oct 28 - Oct 29 [](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](https://images.trvl-media.com/lodging/93000000/92730000/92724000/92723926/91792c28.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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $162 CA $257 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Ashland-Hotels-The-Peerless-Hotel-By-WanderLodges.h92723926.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) ![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) ### Stratford Inn Siskiyou-Hargadine Historic District 9.4/10 Exceptional (1571) "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 $149 CA $167 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.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 (1027) "Great place to stay with our dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $213 CA $256 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-Compass-By-Margaritaville-In-Medford.h76138485.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4020000/4011800/4011768/a9f07da1.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 (1000) "Very charming inn in a very charming historical town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha Coya CA $146 CA $162 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Medford-Hotels-Wine-Country-Inn.h4011768.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1800000/1798100/1798022/12202684.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) "Beautifully appointed with all the amenities you would expect, wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $215 CA $238 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Medford-Hotels-Jacksonvilles-Magnolia-Inn.h1798022.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=2025-11-10&endDate=2025-11-11®ionId=553248635976471666&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown District Hotel Reviews ![Stratford Inn](//images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg) ### Stratford Inn 10/10 Excellent "Comfortable, firm bed. Easily adjusted temperature" [](https://expedia.ca/Medford-Hotels-Stratford-Inn.h2758881.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 is an incredible property! The spaces are unqiue and you can see they have repurposed rooms and renovated things over the years. I love gow sprawling it is and how homey it feels-while still feeling upscale." [](https://expedia.ca/Medford-Hotels-Ashland-Hills-Hotel-Suites.h28139.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 "Loved the waffles, so happy you provided bananas. It was so quiet and convenient and close to my friend’s hospital. Loved the Mexican restaurant so close to the hotel, and no problems parking. 👍" [](https://expedia.ca/Medford-Hotels-Flagship-Inn-Of-Ashland.h42817.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 "Airport shuttle was fine" [](https://expedia.ca/Medford-Hotels-Super-8-By-Wyndham-Central-Pt-Medford.h1281623.Hotel-Information) ![Clarion Pointe Medford](//images.trvl-media.com/lodging/1000000/220000/218700/218641/6a918f34_y.jpg) ### Clarion Pointe Medford 10/10 Excellent "Staff very friendly, breakfast had lots of choices and the area was quiet and safe. " [](https://expedia.ca/Medford-Hotels-Clarion-Pointe.h218641.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 "We got in really late at night and the staff at the front was so welcoming. Breakfast is in a cute diner/pub, but the quality of the food was ho-hum... The room was clean and very cozy. Would stay here again if we go through Medford on our next trip. " [](https://expedia.ca/Medford-Hotels-Rogue-Regency-Inn-And-Suites.h19703.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 "Good place to stay nice rooms just need remodeled" [](https://expedia.ca/Medford-Hotels-Comfort-Inn-Suites.h3448.Hotel-Information) ![Best Western Crater Lake Highway White City/Medford](//images.trvl-media.com/lodging/3000000/2140000/2133600/2133508/ae7ed87d_y.jpg) ### Best Western Crater Lake Highway White City/Medford 10/10 Excellent "Perfect stay before a flight!" [](https://expedia.ca/Medford-Hotels-Best-Western-Crater-Lake-Highway-White-CityMedford.h2133508.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 "Great location and nice room" [](https://expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.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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