Title: Skidmore Academy Historic District Vacation Packages | Holiday Packages & Trips 2026/2027 from Expedia.ca [Skidmore Academy Historic District Travel Guide](https://expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103)[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) ![](https://images.trvl-media.com/place/553248635976482103/8e257b0c-49b6-4a00-9cd9-fbf87a8384c5.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Skidmore Academy Historic District Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Where to stay in Skidmore Academy Historic District Find the best Skidmore Academy Historic District areas and neighborhoods for the activities you enjoy most. [Learn more about Skidmore Academy Historic District](https://expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103) ![Landmark building in Ashland Oregon.](https://images.trvl-media.com/place/553248635976471666/d364eacf-6c97-42f7-8156-e8b8401cdb92.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Historic Downtown District 4 out of top 10 points of interest in this area 4.5/5(2 area reviews) If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Thomas Theatre are top sights worth seeing. [Find hotel + flight trips in Historic Downtown District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Historic%20Downtown%20District&DestID=553248635976471666&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States ](https://images.trvl-media.com/place/553248635976471888/2d665321-38b8-4fb8-8dfd-85c9bdddd663.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. [Find hotel + flight trips in Historic Railroad District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Historic%20Railroad%20District&DestID=553248635976471888&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Street scene in downtown Ashland Oregon state.](https://images.trvl-media.com/place/553248635976473896/3bb45aed-ff93-4c44-aad0-62b3fa65d4ee.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. [Find hotel + flight trips in Siskiyou-Hargadine Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Siskiyou-Hargadine%20Historic%20District&DestID=553248635976473896&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Skidmore Academy Historic District Hotel Deals ![Stratford Inn](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758881/2ce3f8a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stratford Inn 555 Siskiyou Blvd Ashland OR CA $123 CA $137 total Mar 22 - Mar 23 includes taxes & fees 9.4/10 Exceptional! (1,712 reviews) I have stayed several times at the Stratford Inn. It is always so easy to check in and out and again - the breakfast is awesome. Everyone seems to like working there which is a great thing. Reviewed on Mar 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=2758881&PinnedHotelID=2758881&HadPinnedHotel=true®ionId=553248635976482103) ![Rogue Regency Inn Medford Airport](https://images.trvl-media.com/lodging/1000000/20000/19800/19703/75221956_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rogue Regency Inn Medford Airport 2300 Biddle Rd Medford OR Fully refundableReserve now, pay when you stay CA $118 CA $140 total Mar 18 - Mar 19 includes taxes & fees 8.8/10 Excellent! (2,876 reviews) Staff were very friendly and our room was clean and comfy. They are dog friendly and have an onsite bar/restaurant. Reviewed on Mar 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%2F2026&selected=19703&PinnedHotelID=19703&HadPinnedHotel=true®ionId=553248635976482103) ![Compass by Margaritaville in Medford](https://images.trvl-media.com/lodging/77000000/76140000/76138500/76138485/f171fa6c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Compass by Margaritaville in Medford 2399 S Pacific Hwy Medford OR Fully refundableReserve now, pay when you stay CA $196 CA $237 total Mar 22 - Mar 23 includes taxes & fees 9.6/10 Exceptional! (1,003 reviews) The whole place is very vibrant and upbeat. Staff was friendly and cool. Room was super clean. Will definitely stay there again. Reviewed on Mar 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=76138485&PinnedHotelID=76138485&HadPinnedHotel=true®ionId=553248635976482103) [See all 702 properties in Skidmore Academy Historic District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F03%2F2026&endDate=19%2F03%2F2026®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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Frequently asked questions ### How much does a Skidmore Academy Historic District vacation package cost? ### How do I get a cheap travel package to Skidmore Academy Historic District? ### Where should I stay in Skidmore Academy Historic District? ### What are the top hotels in Skidmore Academy Historic District? ### How far in advance should I book my Skidmore Academy Historic District vacation? ### What does an Expedia Skidmore Academy Historic District travel package include? ### What should I know before booking a Skidmore Academy Historic District travel package? ### Can I choose my airline with a Skidmore Academy Historic District Expedia vacation package? ### If I'm not able to travel, can I cancel my Skidmore Academy Historic District vacation package? ### Discover the most popular places to visit in Skidmore Academy Historic District #### 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) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.