Historic Downtown District Travel Guide

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 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 lively festivals 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 entertainment choices and lively festivals.

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

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Rp691.740
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

Rp575.627
per traveller
Ashland Puzzling Adventure
Klamath River- Irongate "Kucascas" Dam Scenic Float

Klamath River- Irongate "Kucascas" Dam Scenic Float

Rp3.229.767
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 Rp2.085.792 per night from 19 Oct to 20 Oct
Rp2.085.792
Rp2.325.722 total
19 Oct - 20 Oct
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,017 reviews)
"Great location!"

Reviewed on 22 Sept 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 Rp3.077.100 per night from 5 Oct to 6 Oct
Rp3.077.100
Rp3.514.406 total
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3-star spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their ...
9.2/10 Wonderful! (1,007 reviews)
"Toilet doesn’t flush all the way unless you keep holding the handle down and then you have to pull up on the handle or it keeps running."

Reviewed on 18 Sept 2025

Ashland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
The price is Rp3.437.144 per night from 28 Sept to 29 Sept
Rp3.437.144
Rp3.832.416 total
28 Sept - 29 Sept
includes taxes & fees
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their 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 30 Aug 2025

McCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is Rp3.787.675 per night from 29 Sept to 30 Sept
Rp3.787.675
Rp4.450.047 total
29 Sept - 30 Sept
includes taxes & fees
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (253 reviews)
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"

Reviewed on 16 Sept 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 Rp1.801.980 per night from 28 Sept to 29 Sept
Rp1.801.980
Rp2.027.228 total
28 Sept - 29 Sept
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,445 reviews)
"Bigand comfort room."

Reviewed on 25 Sept 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 Rp2.105.191 per night from 28 Sept to 29 Sept
Rp2.105.191
Rp2.514.167 total
28 Sept - 29 Sept
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,479 reviews)
Definitely recommend
"Clean room, friendly staff and lots of parking. Location is great close to everything."

Reviewed on 24 Sept 2025

Ashland Hills Hotel & Suites
See all 669 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