Historic Downtown District

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 make plans for a show 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 make plans for a show at Oregon Cabaret Theatre during your trip to 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 stay in Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.

Allen Elizabethan Theatre

Thomas Theatre

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

Thomas Theatre

Angus Bowmer Theatre

You can get tickets for a performance at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its acclaimed theater scene.

Angus Bowmer Theatre

Things to do

Rogue River Family Float & Discovery Park-Rafting and Kayaking

Rogue River Family Float & Discovery Park-Rafting and Kayaking

P6,310
per adult
Rogue River Family Float & Discovery Park-Rafting and Kayaking
Salem Puzzling Adventure

Ashland Puzzling Adventure

P1,982
per traveler
Ashland Puzzling Adventure
Rafting Kikacéki

Kikacéki (Ward's) Canyon

P14,091
per adult
Kikacéki (Ward's) Canyon
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 P7,713 per night from Jul 27 to Jul 28
P7,713
P8,600 total
Jul 27 - Jul 28
includes taxes & fees
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! (1,002 reviews)
Four Out of Five
"The room was very clean. The check in staff was friendly and thorough. There were a lot of breakfast choices available. The only area I gave it a 3 is the room itself. It was definitely dated, and the balcony sliding door didn’t lock. It had a wooden dowel on the inside so someone from the outside ..."

Reviewed on Jul 23, 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 P10,199 per night from Aug 10 to Aug 11
P10,199
P11,658 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this 3-star spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,006 reviews)
"An extremely convenient and pleasant place to stay when coming to town for a play at OSF. Couldn't be better!"

Reviewed on Jul 25, 2025

Ashland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
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! (265 reviews)
"Great, friendly, helpful staff. Walk to the theater, gourmet breakfasts."

Reviewed on Jul 22, 2025

Get rates
McCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is P12,289 per night from Jul 28 to Jul 29
P12,289
P14,455 total
Jul 28 - Jul 29
includes taxes & fees
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! (249 reviews)
"This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. ..."

Reviewed on Jul 23, 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 P6,170 per night from Jul 29 to Jul 30
P6,170
P6,941 total
Jul 29 - Jul 30
includes taxes & fees
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! (2,171 reviews)
"Well managed hotel conveniently located for the airport ."

Reviewed on Jul 23, 2025

Rogue Regency Inn and Suites
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
The price is P5,099 per night from Aug 24 to Aug 25
P5,099
P5,765 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this spa hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,030 reviews)
"Nice hotel friendly staff and clean room"

Reviewed on Jul 25, 2025

Quality Inn & Suites Medford Airport
See all 658 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

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

Historic Railroad District
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Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Siskiyou-Hargadine Historic District
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Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District

Historic Downtown District