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 lively festivals in this walkable area.

Mount Ashland Ski Area
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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 acclaimed theatre scene.

Allen Elizabethan Theatre
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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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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
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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 acclaimed theatre scene and lively festivals.

Thomas 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$56
Per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
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Ashland Puzzling Adventure

S$47
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$171 per night from 29 Jun to 30 Jun
S$171
per night
29 Jun - 30 Jun
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,197 reviews)
Great place
"Stopped for a one night stay o. Our way thru town. Place was nice. Everything comfortable, breakfast was great. Staff were friendly - I’d stay again."

Reviewed on 15 Jun,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$352 per night from 17 Jun to 18 Jun
S$352
per night
17 Jun - 18 Jun
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! (985 reviews)
"All of it was very nice"

Reviewed on 12 Jun,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$287 per night from 17 Jun to 18 Jun
S$287
per night
17 Jun - 18 Jun
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)
"A very clean, comfortable and convenient place to stay"

Reviewed on 3 Jun,2024

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 S$371 per night from 18 Jun to 19 Jun
S$371
per night
18 Jun - 19 Jun
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan ...
9.8/10 Exceptional! (235 reviews)
"Excellent boutique hotel. Walk to all the restaurants and the OSF. Our only negative would be our room on the first floor had a loud neighbor above, and we were right next to the kitchen which gears up early to serve an excellent breakfast."

Reviewed on 7 Jun,2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is S$318 per night from 30 Jun to 1 Jul
S$318
per night
30 Jun - 1 Jul
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (206 reviews)
"This was a lovely stopover in Ashland on our way to Santa Barbara. It is a charming, well run inn. This was Memorial Day weekend so breakfast was not “full service” but what we had was delicious."

Reviewed on 3 Jun,2024

Winchester Inn
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is S$189 per night from 24 Jun to 25 Jun
S$189
per night
24 Jun - 25 Jun
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! (1,517 reviews)
"Great bang for your buck! So grateful to have a place in Ashland we can stay with our dog, too. Walk across the parking lot to Cubans Biazzi for a beautiful classic Italian meal."

Reviewed on 12 Jun,2024

Stratford Inn
See all 586 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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