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 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

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

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

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

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

€36
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Rafting Kikacéki

Kikacéki (Ward's) Canyon

€214
per adult
Kikacéki (Ward's) Canyon
Salem Puzzling Adventure

Ashland Puzzling Adventure

€30
per traveller
Ashland Puzzling Adventure
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 €155 per night from 24 Aug to 25 Aug
€155
24 Aug - 25 Aug
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! (1,006 reviews)
Comfortable in Ashland
"The Bard's Inn is comfortable and welcoming, and an easy stroll down the street to restaurants, shops and the Oregon Shakespeare Festival shows"

Reviewed on 28 Jul 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 €222 per night from 8 Aug to 9 Aug
€222
8 Aug - 9 Aug
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! (1,011 reviews)
"Beautiful old hotel (refurbished) close to everything in Ashland!"

Reviewed on 29 Jul 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 22 Jul 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 €212 per night from 4 Aug to 5 Aug
€212
4 Aug - 5 Aug
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 23 Jul 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 €106 per night from 4 Aug to 5 Aug
€106
4 Aug - 5 Aug
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! (2,193 reviews)
"Good place to stay"

Reviewed on 31 Jul 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 €88 per night from 1 Sept to 2 Sept
€88
1 Sept - 2 Sept
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! (1,043 reviews)
A good value
"The front desk was very friendly and professional (especially Cathy!) and housekeeping did a good job. The hotel does not have an elevator and during my second visit I was assigned a second floor room. I am in my 70s and getting my luggage upstairs would have been difficult so they quickly assigned ..."

Reviewed on 29 Jul 2025

Quality Inn & Suites Medford Airport
See all 654 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

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