Historic Downtown District Travel Guide

Tourist Guide
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 get tickets for a performance 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 entertainment choices in this walkable area.

Mount Ashland Ski Area

Oregon Cabaret Theatre

You can get tickets for a performance at Oregon Cabaret Theatre during your stay in 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 trip to Ashland. Wander around the area's picturesque gardens or experience its acclaimed theatre scene.

Allen Elizabethan Theatre

Thomas Theatre

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

Thomas Theatre

Angus Bowmer Theatre

You can make plans for a show at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its lively festivals.

Angus Bowmer Theatre

Activities

Salem Puzzling Adventure

Ashland Puzzling Adventure

AU$54
Per adult
Ashland Puzzling Adventure
See all activities in Ashland

Our pick of the best Historic Downtown District Hotel Deals

Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is AU$274 per night from 1 Dec to 2 Dec
AU$274
includes taxes & fees
1 Dec - 2 Dec
Stay at this 3-star spa hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,004 reviews)
"Absolutely amazing hotel. We had a perfect room that was quiet. Staff went above and beyond to ensure out stay was great."

Reviewed on 20 Nov. 2024

Ashland Springs Hotel
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 AU$189 per night from 1 Dec to 2 Dec
AU$189
includes taxes & fees
1 Dec - 2 Dec
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! (1,000 reviews)
"nicely appointed, good value, excellent location."

Reviewed on 26 Oct. 2024

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is AU$219 per night from 9 Dec to 10 Dec
AU$219
includes taxes & fees
9 Dec - 10 Dec
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! (230 reviews)
"Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay ..."

Reviewed on 3 Nov. 2024

Winchester Inn
McCall House Boutique Inn
McCall House Boutique Inn
4 out of 5
153 Oak St, Ashland, OR
The price is AU$272 per night from 3 Dec to 4 Dec
AU$272
includes taxes & fees
3 Dec - 4 Dec
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! (248 reviews)
"Great location, walkable to downtown. Breakfasts were excellent and they were able to accommodate special dietary restrictions. Staff is wonderful. Loved it!"

Reviewed on 1 Nov. 2024

McCall House Boutique Inn
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is AU$137 per night from 2 Dec to 3 Dec
AU$137
includes taxes & fees
2 Dec - 3 Dec
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,460 reviews)
"We live this place. The staff is incredible and the pool / hot tub is wonderful"

Reviewed on 24 Nov. 2024

Stratford Inn
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is AU$166 per night from 26 Nov to 27 Nov
AU$166
includes taxes & fees
26 Nov - 27 Nov
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! (1,614 reviews)
"Clean, spacious rooms. On site restaurant and easy access to I-5. Overall, a very good value"

Reviewed on 24 Nov. 2024

Rogue Regency Inn and Suites
See all 638 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

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Historic Railroad District
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Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Siskiyou-Hargadine Historic District
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Skidmore Academy Historic District

While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District

Historic Downtown District Travel Guide

Choose two or more items and save on your trip: