Title: Visit Historic Downtown District: Best of Historic Downtown District, Ashland Travel 2025 | Expedia Tourism - Expedia.ca [Hotels in Historic Downtown District](https://expedia.ca/Historic-Downtown-District-Ashland-Hotels.0-n553248635976471666-0.Travel-Guide-Filter-Hotels)[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) # Historic Downtown District ## Ashland ![Historic Downtown District](https://mediaim.expedia.com/destination/1/2827c471dbf315bcf8c417169ecc676c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/c3984b62b75fb53f290ed89a1a691990.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Shannon Willitts](https://mediaim.expedia.com/destination/2/c3984b62b75fb53f290ed89a1a691990.jpg) ![Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/ed7d471e3db4861665201b87b179f849.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Shannon Willitts](https://mediaim.expedia.com/destination/2/ed7d471e3db4861665201b87b179f849.jpg) ![Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/8349980186958f824e68d97b963a432d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Shannon Willitts](https://mediaim.expedia.com/destination/2/8349980186958f824e68d97b963a432d.jpg) ![Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/886982e4c5154680b400098d913ea7f3.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Shannon Willitts](https://mediaim.expedia.com/destination/2/886982e4c5154680b400098d913ea7f3.jpg) ## Visit Historic Downtown District Things to do Hotels Where to stay [Ashland travel guide](https://expedia.ca/Ashland.dx6290) * * * ### Popular places to visit ![Oregon Shakespeare Festival](https://mediaim.expedia.com/destination/2/e7d42a6fce65f5ab7a72ba316bf31a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oregon Shakespeare Festival You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants. [](https://expedia.ca/Oregon-Shakespeare-Festival-Historic-Downtown-District.d6183594.Vacation-Attraction) ![Mount Ashland Ski Area](https://mediaim.expedia.com/destination/2/73f22d4b9709c52f846261d75ff942ad.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Mount Ashland Ski Area Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and lively festivals in this walkable area. [](https://expedia.ca/Mount-Ashland-Ski-Area-Ashland.d6087455.Vacation-Attraction) #### Oregon Cabaret Theatre You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants. [](https://expedia.ca/Oregon-Cabaret-Theatre-Historic-Downtown-District.d553248621532642225.Vacation-Attraction) #### Allen Elizabethan Theatre You can enjoy a show at Allen Elizabethan Theatre during your stay in Ashland. Wander around the area's picturesque gardens or experience its entertainment choices. [](https://expedia.ca/Allen-Elizabethan-Theatre-Historic-Downtown-District.d6078449.Vacation-Attraction) #### Thomas Theatre You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices. [](https://expedia.ca/Thomas-Theatre-Historic-Downtown-District.d6078459.Vacation-Attraction) #### Angus Bowmer Theatre You can get tickets for a performance at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its lively festivals. [](https://expedia.ca/Angus-Bowmer-Theatre-Historic-Downtown-District.d6078439.Vacation-Attraction) ### Things to do ![Salem Puzzling Adventure](https://mediaim.expedia.com/localexpert/45939288/039b3306-226d-46f0-a7b2-b0db77111871.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ashland Puzzling Adventure CA $48 per traveller [](https://expedia.ca/things-to-do/ashland-puzzling-adventure.a45939288.activity-details) [See all activities in Ashland](https://expedia.ca/Things-To-Do-In-Ashland.d6290.Travel-Guide-Activities) * * * ## Historic Downtown District Hotel Deals ![The Bard's Inn, BW Signature Collection by Best Western](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Bard's Inn, BW Signature Collection by Best Western 132 N Main Street, Ashland, OR CA $152 CA $170 total Nov 1 - Nov 2 includes taxes & fees Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ... 8.6/10 Excellent! (1,023 reviews) "My favorite place to stay in Ashland. Clean and nice rooms, affordable, PERFECT location and great staff!" Reviewed on Sep 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F11%2F2025&endDate=02%2F11%2F2025&selected=9249&PinnedHotelID=9249&HadPinnedHotel=true®ionId=553248635976471666) ![Ashland Springs Hotel](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ashland Springs Hotel 212 E Main St, Ashland, OR CA $244 CA $279 total Oct 5 - Oct 6 includes taxes & fees Stay at this 3-star spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ... 9.2/10 Wonderful! (1,011 reviews) "Second time staying at Ashland Springs. Came to the Oregon Shakespeare Festival for the weekend. Easy parking. Close to restaurants and shopping, very walkable. Great staff. Will be back again next year for sure!" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=660933&PinnedHotelID=660933&HadPinnedHotel=true®ionId=553248635976471666) ![McCall House Boutique Inn](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/c4aac0d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### McCall House Boutique Inn 153 Oak St, Ashland, OR CA $238 CA $266 total Nov 1 - Nov 2 includes taxes & fees Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ... 9.8/10 Exceptional! (270 reviews) Comfy, cozy and convenient "Wonderful place in a very convenient location within easy walking distance of OSF and a range of food, drink and shopping. Very comfortable and cozy, with a friendly, helpful staff." Reviewed on Aug 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F11%2F2025&endDate=02%2F11%2F2025&selected=15153095&PinnedHotelID=15153095&HadPinnedHotel=true®ionId=553248635976471666) ![Winchester Inn](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Winchester Inn 35 S. 2nd St., Ashland, OR CA $259 CA $306 total Oct 27 - Oct 28 includes taxes & fees Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ... 9.6/10 Exceptional! (253 reviews) "Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!" Reviewed on Sep 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=1505812&PinnedHotelID=1505812&HadPinnedHotel=true®ionId=553248635976471666) ![Rogue Regency Inn and Suites](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/8b20e842_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rogue Regency Inn and Suites 2300 Biddle Rd, Medford, OR CA $134 CA $151 total Oct 5 - Oct 6 includes taxes & fees Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ... 8.8/10 Excellent! (2,456 reviews) "This hotel has become my new stop between Reno and Seattle. It’s a full service hotel that is a little on the older side but very well cared for. I really enjoyed my stay. I appreciate that it was truly pet friendly as I travel with my best friend. There is a large field in front of the hotel that ..." Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=19703&PinnedHotelID=19703&HadPinnedHotel=true®ionId=553248635976471666) ![Ashland Hills Hotel & Suites](https://images.trvl-media.com/lodging/1000000/30000/28200/28139/3cd7d8f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ashland Hills Hotel & Suites 2525 Ashland St, Ashland, OR CA $152 CA $183 total Oct 6 - Oct 7 includes taxes & fees Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ... 8.8/10 Excellent! (1,457 reviews) Reviewed on Oct 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=06%2F10%2F2025&endDate=07%2F10%2F2025&selected=28139&PinnedHotelID=28139&HadPinnedHotel=true®ionId=553248635976471666) [See all 670 properties in Historic Downtown District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=553248635976471666) 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. ## Check Historic Downtown District hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-04&endDate=2025-10-05) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-04&endDate=2025-10-05)[Oct 4 - Oct 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-05&endDate=2025-10-06) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-05&endDate=2025-10-06)[Oct 5 - Oct 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=2025-10-05&endDate=2025-10-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)[Oct 10 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976471666&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025) * * * ### Other neighbourhoods around Historic Downtown District ![Default Image](https://mediaim.expedia.com/destination/2/706bfa5fabaff57e835c70e5c4f4c2eb.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Historic Railroad District Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out. [](https://expedia.ca/Ashland-Historic-Railroad-District.dx553248635976471888) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Siskiyou-Hargadine Historic District While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library. [](https://expedia.ca/Ashland-Siskiyou-Hargadine-Historic-District.dx553248635976473896) ![Default Image](https://mediaim.expedia.com/destination/2/87dfcc613b81a05a53a2dabfb311a2f7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Skidmore Academy Historic District Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out. [](https://expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103) * * * * * * - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Historic Downtown District ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAE8klEQVR4Xu3asXEbMRBGYXAUMHQJV4pKA0tTKSzBIQMOYf2LPWDveObMBnZAvZeIBBf4LoNoubT/UNkv/ItAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkiog97Jr0VLtH36Vs35ctV7b7z7wveSjY2nmGxWIBRIDWZdGIBZIDGRdGr0rUue7JuS7y/f8Sch3jpTyq4/c+tKHXv/W1Gh7FogFMgOxQEAaCIh/EG/vRasRCa0n+lttnFMLSF8fgYAoEJACArIOzZcHSFwqutCf8kdpICAgIOvQfAnSX4CAJBHvUcpn/z5tXdav2Fb8ig2iQNZAZiAgIBbI2h6ZOeIn2vbwqS2d9SMiIxCQBmKB1PkOpAcC0vbItqXP2nY78fXSrjpPBjlY2lXnySAHS7vqPBnkYGlXnSeDHCztqvNkkIOlXXWeDHKwtKvOkwNynO74+RXbLvRLmX9zHnf8q0BAjgOJgYAcBxJ7X8Rvb8tu79KRogtdJ5ZxoX/2HbakKcsexX5fqH1BgRQQBQICoh8gIG2D+AcPbY+zfqIveeZa9iiaOvlHY2kEAgICAmKBgKwr8+VdW/yq1id9Nt7eXm1bpIVv3WdtHFMeCAiIPrwUEJA55YGAHHfpyNfziebqx31z4kEgIMeBxEBAjgOJvSXisw99n9Yn3yfe+9F2onXVW58q5ayp0v/AbF+x7Y4PUx4ICAiIfQICMmZARnbi9q/JH/2ON/emC30stXGib/RH8SkQkAYCArJuBAF5hVjzr8mlLNpe++3t2+3E/ZIXnw4EpIGAeCANBOQVYtutrz5rS+qkJWtZhx/jUYqufX86R/aBgICAgIAokLUtonYn+vfpphNbu64nPrl+7XvzgRUICEj/GGTRKggIyA6pza/qMk4U8tD7c5t/c46udSn2dLbkU9U/aiAgID0QEBCQtT0Svzz7ibb9q7/y7fNC11Lrj7LWJ0FAQEBAFv0AAXmNeA9NnMdbbTe37U80d8yZ+9U32i8HIZAG0gMBUSAxkPbjkXihn8OJ1qcN9yVlj2KNqZNe3ORetV7XURAQEBAQvQCxPm0YZL5smp0XumY/xnZz91PzRLUiXh3zICAKBKSBgICsBeTeP3iMsWX9ZJ5oCbHsxKVvnF+xQUA8EAsEBATkJdK03S/0ohMP7vjrZvvWtUextlMgHggICMh+CsT70cjTVb1oVdstP9Gnik686Yfd8TF/uhAICAgICAhILCAH2YlWdFtHSl+yxtTMlxSIBbINJCwpEAtkG0hYUm+J3MOEtWj1EhZ88C/Xvv1yMKs+3UBAQPpGEJC16tMNBMRnZ0J8u3UeS+oUJudG+01gu6RAQEBAFMhuSYGA/O1Ev9DnlC/FE0e29OJfuEFAQEBAYiAN5Blp/Sv2SSd6H9ulsdEy1wd9SYGAgICAgMQTFYh3gPj2p/84Paf8Qr8U++/V1jhrBAICAgICUhtI36H2yExI03a/0M214tTW/VyXPjYjIDMQC8SWQEAaSOwHI9uWvr7dbvk/et/GaG32m0A5fhQQCyS29HWQPqNALJDY0tdB+ox6S+TfBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBU74P8ATtouZWoZimRAAAAAElFTkSuQmCC)