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 lively festivals.

Allen Elizabethan 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 lively festivals.

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 lively festivals and entertainment choices.

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

My Place Hotel-Medford OR
My Place Hotel-Medford OR
3 out of 5
580 Airport Rd, Medford, OR
The price is S$173 per night from 23 May to 24 May
S$173
per night
23 May - 24 May
Stay at this 3-star business-friendly hotel in Medford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (880 reviews)
"Comfortable beds and quiet"

Reviewed on 17 May,2024

My Place Hotel-Medford OR
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is S$321 per night from 26 May to 27 May
S$321
per night
26 May - 27 May
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! (1,005 reviews)
"A very quaint hotel"

Reviewed on 19 May,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
Fully refundableReserve now, pay when you stay
The price is S$225 per night from 23 May to 24 May
S$225
per night
23 May - 24 May
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)
"The property is old, and the comforters need updating, but the location, free breakfast and staff made it worth the stay. Sweetest people ever."

Reviewed on 12 May,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$325 per night from 23 May to 24 May
S$325
per night
23 May - 24 May
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! (231 reviews)
"Beautiful and comfortable, I would get a larger room next time for the price, stayed at the Anthony, seemed more expensive for the size. Used Expedia."

Reviewed on 15 May,2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is S$332 per night from 3 Jun to 4 Jun
S$332
per night
3 Jun - 4 Jun
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! (203 reviews)
"The service was delightful"

Reviewed on 12 May,2024

Winchester Inn
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
The price is S$176 per night from 23 May to 24 May
S$176
per night
23 May - 24 May
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! (1,134 reviews)
"stairs were hard to navigate"

Reviewed on 19 May,2024

Rogue Regency Inn and Suites
See all 597 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