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 entertainment choices.

Angus Bowmer Theatre

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

€40
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

€34
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 €159 per night from 19 Feb to 20 Feb
€159
includes taxes & fees
19 Feb - 20 Feb
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! (1,004 reviews)
"It’s the only place I stay when I’m in southern Oregon."

Reviewed on 12 Feb 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 €117 per night from 19 Feb to 20 Feb
€117
includes taxes & fees
19 Feb - 20 Feb
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! (1,001 reviews)
Weekend Getaway
"Nice place with free breakfast, friendly staff, walk to downtown."

Reviewed on 14 Feb 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
The price is €145 per night from 20 Feb to 21 Feb
€145
includes taxes & fees
20 Feb - 21 Feb
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! (255 reviews)
"Building was gorgeous and interesting, rooms had many nice amenities, breakfast was delicious and price was good."

Reviewed on 1 Feb 2025

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is €136 per night from 3 Mar to 4 Mar
€136
includes taxes & fees
3 Mar - 4 Mar
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! (232 reviews)
"Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and ..."

Reviewed on 14 Jan 2025

Winchester Inn
The Urban Gypsy Loft
The Urban Gypsy Loft
Ashland
Stay at this apartment in Ashland. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Ashland Library and Oregon Cabaret Theatre are located ...
10/10 Exceptional! (1 review)
Charming historic flat on charming Main Street
"This 2 bedroom flat is very spacious, with plenty of room to relax and enjoy your company. The front room has a dining area, and spacious sitting area overlooking Main Street. There is a tv room, 2 bedrooms and a kitchen. It’s is a very cozy, comfortable and homey flat. Walking distance to everywhere ..."

Reviewed on 11 Dec 2024

Get rates
The Urban Gypsy Loft
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is €110 per night from 19 Feb to 20 Feb
€110
includes taxes & fees
19 Feb - 20 Feb
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! (1,746 reviews)
"Easy checkin. Decent price. Restaurant was quite spendy for okay food."

Reviewed on 17 Feb 2025

Rogue Regency Inn and Suites
See all 634 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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