Title: Visit Skidmore Academy Historic District: Best of Skidmore Academy Historic District, Ashland Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Skidmore Academy Historic District](https://expedia.ca/Skidmore-Academy-Historic-District-Ashland-Hotels.0-n553248635976482103-0.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)[Skidmore Academy Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Skidmore-Academy-Historic-District.d553248635976482103.Car-Rental-Guide)[Skidmore Academy Historic District Vacations](https://expedia.ca/Skidmore-Academy-Historic-District.d553248635976482103.Destination-Travel-Guides) # Skidmore Academy Historic District ## Ashland ![Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/87dfcc613b81a05a53a2dabfb311a2f7.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Shannon Willitts ](https://mediaim.expedia.com/destination/2/87dfcc613b81a05a53a2dabfb311a2f7.jpg) ## Visit Skidmore Academy Historic 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 entertainment choices in this walkable area. [](https://expedia.ca/Mount-Ashland-Ski-Area-Ashland.d6087455.Vacation-Attraction) #### Southern Oregon University Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's lively festivals and entertainment choices. [](https://expedia.ca/Southern-Oregon-University-Ashland.d6188400.Vacation-Attraction) #### Lithia Park 5/5(8 reviews) Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area. [](https://expedia.ca/Lithia-Park-Ashland.d553248621532642212.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) #### Howard Prairie Lake Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants. [](https://expedia.ca/Howard-Prairie-Lake-Ashland.d553248621532642226.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 $49 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) --- ## Skidmore Academy Historic District Hotel Deals ![Abigail’s Bed & Breakfast Inn](https://images.trvl-media.com/lodging/5000000/4970000/4966500/4966403/996815d3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Abigail’s Bed & Breakfast Inn 451 North Main Street Ashland OR CA $248 CA $276 total Jan 7 - Jan 8, 2026 includes taxes & fees Stay at this B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Allen Elizabethan Theatre and Angus Bowmer Theatre ... 9.6/10 Exceptional! (42 reviews) Abigail's B & B Abigail's is a lovely B & B and the hosts are quite accommodating. We felt very welcome in their home and were provided several amenities including a blanket and seat cushions for the play we attended in the outdoor Elizabethan Theatre. Reviewed on Jul 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=4966403&PinnedHotelID=4966403&HadPinnedHotel=true®ionId=553248635976482103) ![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 $115 CA $130 total Dec 18 - Dec 19 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! (2,683 reviews) Great breakfast, friendly staff. Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=19703&PinnedHotelID=19703&HadPinnedHotel=true®ionId=553248635976482103) ![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 $124 CA $153 total Jan 1 - Jan 2, 2026 includes taxes & fees Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ... 8.8/10 Excellent! (1,490 reviews) Convenient dog park right on the beautiful hotel grounds. Great for dogs and owners that have been traveling for hours. The staff is warm and friendly. The rooms are spotless and well equipped. I love stopping here! Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=28139&PinnedHotelID=28139&HadPinnedHotel=true®ionId=553248635976482103) ![Stratford Inn](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/b7c87028_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stratford Inn 555 Siskiyou Blvd Ashland OR CA $112 CA $125 total Jan 3 - Jan 4, 2026 includes taxes & fees Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ... 9.2/10 Wonderful! (1,596 reviews) We had a great stay! Haven’t stayed here since 2001\. Happy to report that the Stratford is in great shape and the staff is still friendly, knowledgeable, and super helpful. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=03%2F01%2F2026&endDate=04%2F01%2F2026&selected=2758881&PinnedHotelID=2758881&HadPinnedHotel=true®ionId=553248635976482103) ![Flagship Inn of Ashland](https://images.trvl-media.com/lodging/1000000/50000/42900/42817/f8004dc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Flagship Inn of Ashland 1193 Siskiyou Blvd Ashland OR CA $83 CA $93 total Dec 14 - Dec 15 includes taxes & fees Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ... 8.6/10 Excellent! (1,180 reviews) Room was very clean. We like to stay here. Reasonable rates and good location near the college. Had a little trouble getting keys to work, but the manager quickly took care of it. Breakfast a little skimpy but there is a great restaurant next door called Morning Glory. There is a free charge point ... Reviewed on Dec 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=42817&PinnedHotelID=42817&HadPinnedHotel=true®ionId=553248635976482103) ![My Place Hotel-Medford OR](https://images.trvl-media.com/lodging/66000000/66000000/65997100/65997015/fbc27264_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### My Place Hotel-Medford OR 580 Airport Rd Medford OR CA $110 CA $123 total Dec 24 - Dec 25 includes taxes & fees Book a stay at this business-friendly hotel in Medford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ... 9/10 Wonderful! (1,511 reviews) Great place for the price Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=65997015&PinnedHotelID=65997015&HadPinnedHotel=true®ionId=553248635976482103) [See all 699 properties in Skidmore Academy Historic District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635976482103) 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 Skidmore Academy Historic District hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=2025-12-12&endDate=2025-12-13)[Dec 12 - Dec 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=2025-12-12&endDate=2025-12-13) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=2025-12-13&endDate=2025-12-14)[Dec 13 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=2025-12-13&endDate=2025-12-14) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025)[Dec 12 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976482103&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025) --- ### Other neighbourhoods around Skidmore Academy Historic District ![Default Image](https://mediaim.expedia.com/destination/1/2827c471dbf315bcf8c417169ecc676c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Historic Downtown District 4.5/5(2 area reviews) If you're spending some time in Historic Downtown District, Thomas Theatre and Oregon Shakespeare Festival are top sights worth seeing. [](https://expedia.ca/Ashland-Historic-Downtown-District.dx553248635976471666) ![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 Thomas Theatre and Oregon Shakespeare Festival 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) --- --- - [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) # Skidmore Academy Historic District ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [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) - [Aparthotels in Ashland ](https://www.expedia.ca/Ashland-Apart-Hotels.d6290-aaApartHotels.Travel-Guide-Accommodation) - 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