Historic Downtown District, OR

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

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 reviews)

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
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

4/5(70 reviews)

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

4.5/5(47 reviews)

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 acclaimed theater scene.

Allen Elizabethan Theatre

Thomas Theatre

4.5/5(81 reviews)

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

Historic Downtown District Hotel Deals

Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is AED 498 per night from Feb 9 to Feb 10
AED 498
AED 574 total
includes taxes & fees
9 Feb - 10 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! (1,001 reviews)
Disappointed.
"We have stayed here several times over the years & it’s always beautiful. Our room this time was SUPER crowded. Way too much furniture. It was also snowing and there was no attempt to have the parking lot or surrounding areas plowed or shoveled. The front sidewalk and drop off area at a minimum should ..."

Reviewed on 5 February 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 AED 404 per night from Feb 12 to Feb 13
AED 404
AED 450 total
includes taxes & fees
12 Feb - 13 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! (1,000 reviews)
"Nice property walking distance to the Ashland Plaza. Underground parking, comfortable bed, and very quiet!"

Reviewed on 2 February 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 AED 503 per night from Feb 9 to Feb 10
AED 503
AED 561 total
includes taxes & fees
9 Feb - 10 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! (253 reviews)
"Building was gorgeous and interesting, rooms had many nice amenities, breakfast was delicious and price was good."

Reviewed on 1 February 2025

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is AED 352 per night from Feb 10 to Feb 11
AED 352
AED 425 total
includes taxes & fees
10 Feb - 11 Feb
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! (239 reviews)
Wonderful
"The Winchester, especially the Hargadine Suite, is the best hotel on the west coast. I love it so much it is a very very uniquely special place. I go to Ashland specifically for the Winchester and their amazing breakfast."

Reviewed on 20 January 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 AED 377 per night from Feb 9 to Feb 10
AED 377
AED 424 total
includes taxes & fees
9 Feb - 10 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! (1,729 reviews)
"Nice place due to restarunt"

Reviewed on 7 February 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is AED 356 per night from Feb 23 to Feb 24
AED 356
AED 434 total
includes taxes & fees
23 Feb - 24 Feb
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,477 reviews)
"Great service"

Reviewed on 1 February 2025

Ashland Hills Hotel & Suites
See all 643 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 neighborhoods around Historic Downtown District

Road trip food!! I loved the burrito bowl

Historic Railroad District

4.5/5(7 area reviews)

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

Historic Railroad District
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Siskiyou-Hargadine Historic District

4.5/5(12 area reviews)

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

Siskiyou-Hargadine Historic District
Walked across the street from the ER and imagine this was the view from a physician parking lot

Skidmore Academy Historic District

5/5(1 area review)

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

Skidmore Academy Historic District

Historic Downtown District, OR

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