Historic Downtown District

Ashland

Historic Downtown District
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts

Popular places to visit

Oregon Shakespeare Festival

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.

Oregon Shakespeare Festival
Mount Ashland Ski 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.

Mount Ashland Ski Area

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.

Oregon Cabaret Theatre

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.

Allen Elizabethan Theatre

Thomas Theatre

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's entertainment choices and lively festivals.

Thomas Theatre

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 lively festivals.

Angus Bowmer Theatre

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

P1,992
per traveler
Ashland Puzzling Adventure
Klamath River- Irongate "Kucascas" Dam Scenic Float

Klamath River- Irongate "Kucascas" Dam Scenic Float

P11,177
per adult
Klamath River- Irongate "Kucascas" Dam Scenic Float
See all activities in Ashland

Top hotels in Historic Downtown District

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street, Ashland, OR
The price is P8,854 per night from Oct 1 to Oct 2
P8,854
per night
Oct 1 - Oct 2
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,003 reviews)
"I always stay at the Bards Inn when in Ashland."

Reviewed on Sep 7, 2025

The Bard's Inn, BW Signature Collection by Best Western
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St, Ashland, OR
The price is P14,990 per night from Sep 22 to Sep 23
P14,990
per night
Sep 22 - Sep 23
Stay at this 3-star spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,000 reviews)
Great stay not long enough
"Everything was as expected. Perfect! Wish i would have booked 1 more night. Looking for a room the day i checked out was horrible. I traveled from Salem to relax ended up driving home Wednesday after i played golf since i had nowhere to stay."

Reviewed on Sep 11, 2025

Ashland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
The price is P11,764 per night from Sep 28 to Sep 29
P11,764
per night
Sep 28 - Sep 29
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.8/10 Exceptional! (270 reviews)
Comfy, cozy and convenient
"Wonderful place in a very convenient location within easy walking distance of OSF and a range of food, drink and shopping. Very comfortable and cozy, with a friendly, helpful staff."

Reviewed on Aug 30, 2025

McCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is P15,358 per night from Sep 29 to Sep 30
P15,358
per night
Sep 29 - Sep 30
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (252 reviews)
"Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close ..."

Reviewed on Sep 8, 2025

Winchester Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is P6,169 per night from Sep 18 to Sep 19
P6,169
per night
Sep 18 - Sep 19
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! (2,373 reviews)
Stay Rogue (Hotel) for One Night
"This hotel was much bigger than I had anticipated. The Cafe & Grill had amazing staff with drinks to match. If you get a chance to order the cheese curds- do it!!?"

Reviewed on Sep 10, 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is P6,796 per night from Sep 28 to Sep 29
P6,796
per night
Sep 28 - Sep 29
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,451 reviews)
"Always enjoy our stay in Ashland. Quiet and spacious rooms."

Reviewed on Sep 9, 2025

Ashland Hills Hotel & Suites
See all 670 properties in Historic Downtown District
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.

Other neighbourhoods around Historic Downtown District

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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.

Historic Railroad District
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Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Siskiyou-Hargadine Historic District
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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.

Skidmore Academy Historic District

Historic Downtown District