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

Thomas Theatre

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

Thomas 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

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

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

AU$68
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

AU$56
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
The price is AU$251 per night from 7 Jan to 8 Jan
AU$251
includes taxes & fees
7 Jan - 8 Jan
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! (1,003 reviews)
"Great spot in Ashland. Close to everything and a great place to unwind after a day of exploring town. Felt cozy and comfortable! I will definitely be returning."

Reviewed on 31 Dec. 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$215 per night from 6 Jan to 7 Jan
AU$215
includes taxes & fees
6 Jan - 7 Jan
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)
"large puddle near door to my room excessively noisy H-Vac system. your listing said hotel was pet friendly but did not indicate that they would charge an additional $20 dollars for my pet"

Reviewed on 2 Jan. 2025

The Bard's Inn, BW Signature Collection by Best Western
McCall House Boutique Inn
McCall House Boutique Inn
4 out of 5
153 Oak St, Ashland, OR
The price is AU$231 per night from 7 Jan to 8 Jan
AU$231
includes taxes & fees
7 Jan - 8 Jan
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! (247 reviews)
"Beautiful setting and room."

Reviewed on 30 Dec. 2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is AU$213 per night from 13 Jan to 14 Jan
AU$213
includes taxes & fees
13 Jan - 14 Jan
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! (232 reviews)
Great place, but.....
"The place and staff is fabulous. Always like it. Sorry to say I have the same complaint now as last time we were there, and we stayed in a different room. The carpets were filthy. Even if they were clean, they looked horrible with all the stains. How about hard wood floors or..... Thanks for ..."

Reviewed on 3 Jan. 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 AU$175 per night from 8 Jan to 9 Jan
AU$175
includes taxes & fees
8 Jan - 9 Jan
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! (1,682 reviews)
"Excellent property, room and service."

Reviewed on 3 Jan. 2025

Rogue Regency Inn and Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is AU$143 per night from 6 Jan to 7 Jan
AU$143
includes taxes & fees
6 Jan - 7 Jan
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! (1,417 reviews)
"Most restaurants were closed"

Reviewed on 4 Jan. 2025

Stratford Inn
See all 632 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 Oregon Shakespeare Festival 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 Oregon Shakespeare Festival and Oregon Cabaret Theatre.

Skidmore Academy Historic District

Historic Downtown District Travel Guide

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