Title: Book the Best HISTORIC Hotels in Ashland in 2026 | Expedia.ca [Ashland Travel Guide](https://expedia.ca/Ashland.dx6290)[Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d6290.Travel-Guide-Hotels)[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)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d6290.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.ca/Ashland.d6290.Destination-Travel-Guides) ![APB2G7 Shops and restaurants on Lithia Plaza at junction with Main Street in Ashland Oregon](https://images.trvl-media.com/place/6290/b205cc7b-4899-4c00-bc7b-b6c200d21d53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6290/b205cc7b-4899-4c00-bc7b-b6c200d21d53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Ashland Historic Hotels Tonight [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2026-01-25&endDate=2026-01-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6290&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ashland historic hotels ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/cd01e6a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/405a1648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/549e4bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ashland Springs Hotel [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) Historic Downtown District 9.2/10 Wonderful (1,014 reviews) "Room was clean, breakfast was excellent, staff was knowledgeable, pleasant, and eager to help. Outstanding stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ted CA $119 CA $153 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/24000000/23780000/23777800/23777789/3287754b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23780000/23777800/23777789/4cf1c270.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23780000/23777800/23777789/3e7f7c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/24000000/23780000/23777800/23777789/3d87739e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub [](https://www.expedia.ca/Central-Point-Hotels-Pet-Friendly.h23777789.Hotel-Information) Central Point 9.8/10 Exceptional (104 reviews) "The stay was private and great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bradley s. CA $107 CA $213 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Central-Point-Hotels-Pet-Friendly.h23777789.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/77f797af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/c69262cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/179be120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34280000/34275000/34274911/66e6cdee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT [](https://www.expedia.ca/Jacksonville-Hotels-Lily-Pad-1-BEST-LOCATION.h34274911.Hotel-Information) Jacksonville Historic District 10/10 Exceptional (46 reviews) "This place was awesome. Perfect location for walking to restaurants and Britt. The whole place was very clean. Looking forward to staying again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen H. CA $196 CA $419 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Jacksonville-Hotels-Lily-Pad-1-BEST-LOCATION.h34274911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45470000/45469100/45469029/4357cfcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/46000000/45470000/45469100/45469029/33caf90a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45470000/45469100/45469029/8de78e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/46000000/45470000/45469100/45469029/e91ad8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 5BR mountain-top retreat with private pool, breathtaking views, and total privacy. Sleeps 14 with spacious living areas, gourmet kitchen, and kid-friendly game space. Minutes to Jacksonville, wineries, and Ashland. [](https://www.expedia.ca/Jacksonville-Hotels-Luxury-5BR-Mountain-Top-Retreat-With-Private-Pool.h45469029.Hotel-Information) Jacksonville 9.8/10 Exceptional (79 reviews) "The property was wonderful for a group getaway, with many comfortable bedrooms and large, open communal spaces. While we were on a girl's trip, we'd absolutely consider coming back with the families as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Breah S. CA $806 CA $1,425 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Jacksonville-Hotels-Luxury-5BR-Mountain-Top-Retreat-With-Private-Pool.h45469029.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=2026-02-07&endDate=2026-02-08®ionId=6290&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![Timbers INN and Suites](https://images.trvl-media.com/lodging/1000000/920000/916000/915968/7580c086_y.jpg) ### Timbers INN and Suites 10/10 Excellent "They do allow pets. I was in a non-pet room without a pet. The room was really clean. Everything in the room is well taken care of and cleaned the fridge the microwave all of it they clean the tub the toilet, the counters really well the decor and the paint job was offset and very pretty, and they even have art in the room" [](https://expedia.ca/Medford-Hotels-Timbers-Motel.h915968.Hotel-Information) ![Ashland Springs Hotel](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91_y.jpg) ### Ashland Springs Hotel 10/10 Excellent "Room was clean, breakfast was excellent, staff was knowledgeable, pleasant, and eager to help. Outstanding stay!" [](https://expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Callahan's Mountain Lodge](https://images.trvl-media.com/lodging/13000000/12380000/12372400/12372363/2d34db80_y.jpg) ### Callahan's Mountain Lodge 10/10 Excellent "The front desk was run by Jax. He did a great job of greeting us. He knew who we were and took us to our room. Showed us both the games room and weight room. Informed us the breakfast was served in the dinning room between 7:30 and 9:30\. The room was excellent, very comfortable and clean. Breakfast was more than advertised. The next morning they cleared new fallen snow from our car. We are very pleased with Callahan's." [](https://expedia.ca/Medford-Hotels-Callahans-Mountain-Lodge.h12372363.Hotel-Information) ![McCall House Boutique Inn](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/c4aac0d0_y.jpg) ### McCall House Boutique Inn 10/10 Excellent "Limited iptions for breafast" [](https://expedia.ca/Medford-Hotels-McCall-House-Boutique-Inn.h15153095.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Ashland? ### What's the best place to stay in Ashland to absorb the local history? ### How many historically relevant hotels are located in Ashland? ### What are the must-see historical places and other sights in Ashland? ### What is a historic hotel like in Ashland? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Ashland have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Hotels near Allen Elizabethan Theatre ](https://www.expedia.ca/Allen-Elizabethan-Theatre-Hotels.0-l6078449-0.Travel-Guide-Filter-Hotels) - 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[Flights from San Francisco (SFO) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/sfo/ahm/san-francisco-to-ashland) - [Flights from San José (SJO) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/sjo/ahm/san-jose-to-ashland) - [Flights from Sacramento (SMF) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/smf/ahm/sacramento-to-ashland) - [Flights from Sydney (SYD) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/syd/ahm/sydney-to-ashland) - [Flights from Edmonton (YEG) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/yeg/ahm/edmonton-to-ashland) - [Flights from Regina (YQR) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/yqr/ahm/regina-to-ashland) - [Flights from Winnipeg (YWG) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/ywg/ahm/winnipeg-to-ashland) - [Flights from Toronto (YYZ) to Ashland (AHM) ](https://www.expedia.ca/lp/flights/yyz/ahm/toronto-to-ashland) - [Visit Skidmore Academy Historic District ](https://www.expedia.ca/Ashland-Skidmore-Academy-Historic-District.dx553248635976482103) - [Edenvale Winery ](https://www.expedia.ca/EdenVale-Winery-Medford.d6087459.Vacation-Attraction) - [Visit Medford ](https://www.expedia.ca/Medford.dx602702) - [Thomas Theatre ](https://www.expedia.ca/Thomas-Theatre-Historic-Downtown-District.d6078459.Vacation-Attraction) - [Car rental Talent ](https://www.expedia.ca/Car-Rentals-In-Talent.d6347896.Car-Rental-Guide) - [Book Historic Hotels in Ashland on Expedia.com ](https://www.expedia.com/Ashland-Hotels-Historic-Hotel.0-0-d6290-tHistoricHotel.Travel-Guide-Filter-Hotels)