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

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

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

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

Salem Puzzling Adventure

Ashland Puzzling Adventure

P2,041
per traveler
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
Fully refundableReserve now, pay when you stay
The price is P7,365 per night from 30 Jan to 31 Jan
P7,365
P8,505 total
includes taxes & fees
Jan 30 - Jan 31
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! (1,003 reviews)
"Lovely property and rooms, centrally located."

Reviewed on Jan 18, 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 P6,437 per night from 22 Jan to 23 Jan
P6,437
P7,178 total
includes taxes & fees
Jan 22 - Jan 23
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)
"This was such a fun quirky place to stay. They take pets - we were traveling with our cat. The entire place is themed with a renaissance theme down to the stationary. There were some dated fixtures but the room felt super homey and was very clean and comfortable. It was also very quiet. We barely ..."

Reviewed on Jan 4, 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 P7,900 per night from 22 Jan to 23 Jan
P7,900
P8,809 total
includes taxes & fees
Jan 22 - Jan 23
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! (251 reviews)
"Beautiful setting and room."

Reviewed on Dec 30, 2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is P6,961 per night from 3 Feb to 4 Feb
P6,961
P8,321 total
includes taxes & fees
Feb 3 - Feb 4
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! (237 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 Jan 20, 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 P5,671 per night from 22 Jan to 23 Jan
P5,671
P6,379 total
includes taxes & fees
Jan 22 - Jan 23
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! (1,697 reviews)
No free breakfast
"The hotel offered a free breakfast, but when I got the breakfast they told me only the coffee was free, and i had to pay for the food."

Reviewed on Jan 18, 2025

Rogue Regency Inn and Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is P4,682 per night from 22 Jan to 23 Jan
P4,682
P5,220 total
includes taxes & fees
Jan 22 - Jan 23
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (1,506 reviews)
"Great place to stay!"

Reviewed on Jan 18, 2025

Stratford Inn
See all 638 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

Road trip food!! I loved the burrito bowl

Historic Railroad District

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

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

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

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