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 entertainment choices.

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 acclaimed theatre scene.

Angus Bowmer Theatre

Activities

Salem Puzzling Adventure

Ashland Puzzling Adventure

AU$53
per traveller
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
Fully refundableReserve now, pay when you stay
The price is AU$327 per night from 31 Aug to 1 Sept
AU$327
31 Aug - 1 Sept
includes taxes & fees
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)
"Historic hotel on Main Street within easy reach of all Ashland offers. We had a corner room on the 8th floor; high ceilings and big windows with lovely views of the Rogue Valley hillsides. Decor & amenities a bit dated (especially carpets & upholstery). But bed was comfortable and staff friendly ..."

Reviewed on 4 Aug. 2025

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$272 per night from 24 Aug to 25 Aug
AU$272
24 Aug - 25 Aug
includes taxes & fees
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! (1,004 reviews)
"This property is on Main Street and walkable to the historic Main St. Our room smelled like urine and I realized that I had booked a pet friendly room without knowing it. The front staff graciously upgraded us to a pet free room."

Reviewed on 9 Aug. 2025

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$385 per night from 18 Aug to 19 Aug
AU$385
18 Aug - 19 Aug
includes taxes & fees
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! (249 reviews)
"This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. ..."

Reviewed on 23 Jul. 2025

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
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! (267 reviews)
"Great location , good breakfast but could use a little modernization"

Reviewed on 7 Aug. 2025

Get rates
McCall House Boutique Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is AU$186 per night from 12 Aug to 13 Aug
AU$186
12 Aug - 13 Aug
includes taxes & fees
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! (2,241 reviews)
"Rooms clean, everything was do convenient, restaurant and the airport was just down the road, quick and easy to get to."

Reviewed on 10 Aug. 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 AU$231 per night from 11 Aug to 12 Aug
AU$231
11 Aug - 12 Aug
includes taxes & fees
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! (1,463 reviews)
"This was a clean, well maintained hotel with a friendly helpful staff. The breakfasts were delicious! It was in a great location so that we could visit the Oregon Shakespeare festival and other downtown restaurants. The pool and hot tub were wonderful!"

Reviewed on 5 Aug. 2025

Ashland Hills Hotel & Suites
See all 656 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

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