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

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

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

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

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

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

€38
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

€32
per traveller
Ashland Puzzling Adventure
See all activities in Ashland

Top hotels in Historic Downtown District

Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is €156 per night from 21 Apr to 22 Apr
€156
includes taxes & fees
21 Apr - 22 Apr
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! (1,009 reviews)
Teenie Tiny lol
"Cute area of town, pet friendly. We were staying only overnight but for those staying longer just know (at least in our case) We got a single Queen Bedroom an doh baby...this is a small room lol. Like one side of the bed maybe had 8" of clearance to the wall the other had the night table which was ..."

Reviewed on 12 Apr 2025

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 €107 per night from 23 Apr to 24 Apr
€107
includes taxes & fees
23 Apr - 24 Apr
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)
"From the easy check-in process to the personalized maid/cleaning service to the complimentary breakfast that was surprisingly good and had many choices for us, The Bard’s Inn was the perfect lodging place for our return to Ashland after a long absence. We will definitely book a room again this fall ..."

Reviewed on 16 Apr 2025

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
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! (259 reviews)
"close to center of town"

Reviewed on 21 Mar 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 €254 per night from 20 Apr to 21 Apr
€254
includes taxes & fees
20 Apr - 21 Apr
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! (242 reviews)
"Loved our stay so much!"

Reviewed on 19 Mar 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 €107 per night from 1 May to 2 May
€107
includes taxes & fees
1 May - 2 May
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 ...
9/10 Wonderful! (1,877 reviews)
"Great place to stay for an overnight stop with a dog, with no doggy smell or stains. Very friendly staff."

Reviewed on 16 Apr 2025

Rogue Regency Inn and Suites
Springhill Suites By Marriott Medford Airport
Springhill Suites By Marriott Medford Airport
3 out of 5
3519 HEATHROW WAY, Medford, OR
The price is €109 per night from 25 Apr to 26 Apr
€109
includes taxes & fees
25 Apr - 26 Apr
Stay at this 3-star business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (812 reviews)
"Staff was great. Really liked the facility and will stay here again."

Reviewed on 15 Apr 2025

Springhill Suites By Marriott Medford Airport
See all 639 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, Ashland Library and Oregon Cabaret 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, Ashland Library and Lithia Park 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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