Title: Book the Best Historic Downtown District ALL INCLUSIVE Resorts and Hotels - All-inclusive Hotels in Historic Downtown District, Ashland | 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) ![Landmark building in Ashland Oregon.](https://images.trvl-media.com/place/553248635976471666/d364eacf-6c97-42f7-8156-e8b8401cdb92.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find All Inclusive Resorts and Hotels in Historic Downtown District, Ashland - ![](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 All Inclusive Resorts and Hotels Tonight [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2025-12-31&endDate=2026-01-01&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 1 - Jan 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2026-01-01&endDate=2026-01-02&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976471666&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=ALL_INCLUSIVE&mealPlan=ALL_INCLUSIVE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Historic Downtown District ![Garden](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/86190d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/c5aa855a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/1000000/670000/661000/660933/5e44a7f8.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) ### Ashland Springs Hotel [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) Historic Downtown District 9.2/10 Wonderful (1003) "Small room but wonderful view and comfortable bed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $119 CA $153 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Medford-Hotels-Ashland-Springs-Hotel.h660933.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/80dea5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/4615a2ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/4ed86249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9300/9249/b907a781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bard's Inn, BW Signature Collection by Best Western [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) Historic Downtown District 8.6/10 Excellent (1001) "The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne CA $144 CA $160 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Medford-Hotels-The-Bards-Inn.h9249.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/c4aac0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/d524dba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/d1de8521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/16000000/15160000/15153100/15153095/fac9b352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### McCall House Boutique Inn [](https://www.expedia.ca/Medford-Hotels-McCall-House-Boutique-Inn.h15153095.Hotel-Information) Historic Downtown District 9.2/10 Wonderful (580) "The room was very clean, meals were excellent. Staff was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renae [](https://www.expedia.ca/Medford-Hotels-McCall-House-Boutique-Inn.h15153095.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/684defd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Barbara Howard)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/815c2dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (Silverdale) | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a170cf24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505812/a65795fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester Inn [](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information) Historic Downtown District 9.8/10 Exceptional (264) "Beautiful B&B. This will now be our favorite stop in Ashland. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Willy CA $199 CA $237 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Medford-Hotels-Winchester-Inn.h1505812.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99670000/99664500/99664494/w1920h1079x0y1-9421166c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99664500/99664494/w1914h1080x3y0-5dae51e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms](https://images.trvl-media.com/lodging/100000000/99670000/99664500/99664494/7b8054b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99670000/99664500/99664494/w1920h1077x0y3-eb847001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom historic home with two king beds and kitchenette. [](https://www.expedia.ca/Ashland-Hotels-Spacious-2-Bedroom-Historic-Home-With-King-And-Queen-Beds-And-Kitchenette.h99664494.Hotel-Information) Historic Downtown District 10/10 Exceptional (3) "Great location, nice place to stay. Could use a frying pan." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen B. CA $219 CA $475 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Ashland-Hotels-Spacious-2-Bedroom-Historic-Home-With-King-And-Queen-Beds-And-Kitchenette.h99664494.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663732/w1608h1079x160y1-7b5ce958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663732/c355cfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663732/w1920h1079x0y1-6c09cd75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663732/ca268196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests. [](https://www.expedia.ca/Ashland-Hotels-5-Bedroom-Historic-Home-With-Brand-New-Furnishings.h99663732.Hotel-Information) Historic Downtown District 10/10 Exceptional (4) "Excellent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karl B. CA $404 CA $948 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Ashland-Hotels-5-Bedroom-Historic-Home-With-Brand-New-Furnishings.h99663732.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/100000000/99670000/99664400/99664351/w1216h866x17y17-d58f9e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/100000000/99670000/99664400/99664351/w1282h864x18y18-fd74d0c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99670000/99664400/99664351/w1914h1080x3y0-687a6484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/100000000/99670000/99664400/99664351/a2ee2c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury condo with king bedroom, two bathrooms, full kitchen. [](https://www.expedia.ca/Ashland-Hotels-Luxury-Condo-With-King-Bedroom.h99664351.Hotel-Information) Historic Downtown District 10/10 Exceptional (9) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine W. CA $409 CA $704 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Ashland-Hotels-Luxury-Condo-With-King-Bedroom.h99664351.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/100000000/99670000/99662900/99662834/w1280h864x18y18-cc633d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/100000000/99670000/99662900/99662834/w1165h868x16y16-81a130bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/100000000/99670000/99662900/99662834/w1231h866x17y17-caa4d2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99670000/99662900/99662834/w1244h864x18y18-386a3860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury condo with king bedroom, two bathrooms, full kitchen. [](https://www.expedia.ca/Ashland-Hotels-Luxury-Condo-With-King-Bedroom.h99662834.Hotel-Information) Historic Downtown District 10/10 Exceptional (9) "A wonderful place in a perfect location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary W. CA $375 CA $676 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Ashland-Hotels-Luxury-Condo-With-King-Bedroom.h99662834.Hotel-Information) ![Fridge, microwave, stovetop](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663726/7a9c5c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663726/a5c2bda3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663726/w1284h917x0y7-496240cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms](https://images.trvl-media.com/lodging/100000000/99670000/99663800/99663726/w1914h1080x3y0-26932336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-story, 3 bedroom modern home with king and queen beds, living room and kitchen. [](https://www.expedia.ca/Ashland-Hotels-2-Story.h99663726.Hotel-Information) Historic Downtown District 10/10 Exceptional (12) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie H. CA $267 CA $569 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Ashland-Hotels-2-Story.h99663726.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/100000000/99670000/99664000/99663995/w1608h1079x160y1-ce641b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms](https://images.trvl-media.com/lodging/100000000/99670000/99664000/99663995/8365d3e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99670000/99664000/99663995/a1f238ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/100000000/99670000/99664000/99663995/c8685292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette. [](https://www.expedia.ca/Ashland-Hotels-3-Bedrooms-Include-A-King-And-Two-Queen-Size-Beds.h99663995.Hotel-Information) Historic Downtown District CA $219 CA $518 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Ashland-Hotels-3-Bedrooms-Include-A-King-And-Two-Queen-Size-Beds.h99663995.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=2026-01-14&endDate=2026-01-15®ionId=553248635976471666&adults=2&mealPlan=ALL_INCLUSIVE&sort=RECOMMENDED&openPlayBack=true) ## Top Historic Downtown District Hotel Reviews ## Frequently asked questions ### Looking for Historic Downtown District all-inclusive resorts? ### What is there to do near my all-inclusive resort in Historic Downtown District? ## 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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