Historic Downtown District, OR
Ashland
Visit Historic Downtown District
Popular places to visit
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.
Lithia Park
Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and lively festivals in this family-friendly area.
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.
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 acclaimed theater scene.
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.
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 acclaimed theater scene.
Things to do
Historic Downtown District Hotel Deals
Ashland Springs Hotel
Just a block from the Shakespeare Festival, this hotel is ideally located. Room was clean as were common areas. Chairs in the room were cute, but could use some stuffing. Breakfast was good deal at $5…a step up from chain hotel breakfasts.
Reviewed on Apr 7, 2026
The Bard's Inn, BW Signature Collection by Best Western
food good parking good
Reviewed on Apr 12, 2026
Winchester Inn
Lovely establishment, made to order breakfast, easy walking to theaters.
Reviewed on Apr 8, 2026
McCall House Boutique Inn
It has a great location, easy to walk to center of town. The breakfasts were very fresh and warm. They had 3 or 4 different EV chargers behind the lovely historic house.
Reviewed on Mar 31, 2026
Stratford Inn
For an obviously older hotel, everything was clean, up-to-date, and comfortable. The breakfast was lovely including Gluten Free.
Reviewed on Apr 13, 2026
Rogue Regency Inn Medford Airport
I normally stay next door at the Comfort Inn, but Regency has higher ratings on Expedia so I wanted to try it. Room floor was not clean, with numerous carpet stains as well as visible debris that should have been vacuumed/ swept. Beds are extremely uncomfortable. Breakfast was no better than other ...
Reviewed on Apr 14, 2026
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Other neighborhoods around Historic Downtown District
Historic Railroad District
Historic Railroad District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.
Siskiyou-Hargadine Historic District
While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.
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.
