Historic Downtown District

Ashland
Historic Downtown District

Popular places to visit

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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
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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
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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
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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
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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
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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

Things to do

Image for Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$55
Per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
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Ashland Puzzling Adventure

S$46
Per adult
Ashland Puzzling Adventure
See all activities in Ashland

Top hotels in Historic Downtown District

Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is S$127 per night from 18 Oct to 19 Oct
S$127
per night
18 Oct - 19 Oct
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! (1,507 reviews)
"Excellent!"

Reviewed on 25 Sep,2024

Rogue Regency Inn and Suites
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is S$340 per night from 29 Sep to 30 Sep
S$340
per night
29 Sep - 30 Sep
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! (1,001 reviews)
"Rooms are smaller than modern hotels but it was clean and had all we needed. Great experience with staff, location was ideal for plays."

Reviewed on 23 Sep,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 S$186 per night from 29 Oct to 30 Oct
S$186
per night
29 Oct - 30 Oct
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 ...
8.8/10 Excellent! (1,000 reviews)
"Walkable to festival plays!"

Reviewed on 17 Sep,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 S$265 per night from 30 Sep to 1 Oct
S$265
per night
30 Sep - 1 Oct
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! (224 reviews)
"Beautiful"

Reviewed on 21 Sep,2024

Winchester Inn
McCall House Boutique Inn
McCall House Boutique Inn
4 out of 5
153 Oak St, Ashland, OR
The price is S$251 per night from 29 Oct to 30 Oct
S$251
per night
29 Oct - 30 Oct
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! (243 reviews)
"We escaped for a mother and daughters weekend to see Macbeth at OSF. The McCall House was perfect, within walking distance to the theatre, downtown shops, and food. The room was adorable, breakfast was prepared with care and delicious. The Staff made us feel like cherished house guests."

Reviewed on 2 Sep,2024

McCall House Boutique Inn
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is S$219 per night from 7 Oct to 8 Oct
S$219
per night
7 Oct - 8 Oct
Book a stay at this ski hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,503 reviews)
"Easy access from the freeway, limited breakfast buffet, somewhat dated deco."

Reviewed on 24 Sep,2024

Ashland Hills Hotel & Suites
See all 623 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

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