Historic Downtown District Travel Guide

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 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

Salem Puzzling Adventure

Ashland Puzzling Adventure

฿1,143
per traveller
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

฿1,373
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

฿1,114
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 ฿4,735 per night from 1 Nov to 2 Nov
฿4,735
฿5,443 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this 3-star spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their ...
9.2/10 Wonderful! (1,006 reviews)
"Lovely music & coffee on the mezzanine in a.m. Beautiful decor. Comfortable bedding. Tea & cookies on the mezzanine in the afternoon. An orientation to amenities on arrival would have been helpful."

Reviewed on 4 Oct 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
Fully refundableReserve now, pay when you stay
The price is ฿3,225 per night from 14 Nov to 15 Nov
฿3,225
฿3,596 total
14 Nov - 15 Nov
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.6/10 Excellent! (1,005 reviews)
"Great location and nice room"

Reviewed on 18 Oct 2025

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is ฿5,904 per night from 27 Oct to 28 Oct
฿5,904
฿6,976 total
27 Oct - 28 Oct
includes taxes & fees
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.6/10 Exceptional! (255 reviews)
"Lovely room"

Reviewed on 15 Oct 2025

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
The price is ฿5,563 per night from 1 Nov to 2 Nov
฿5,563
฿6,203 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.8/10 Exceptional! (272 reviews)
"Location was very convenient to walking everywhere. Breakfast was fresh and delicious."

Reviewed on 12 Oct 2025

McCall House Boutique Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is ฿3,518 per night from 24 Oct to 25 Oct
฿3,518
฿3,958 total
24 Oct - 25 Oct
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,514 reviews)
"We arrived late from the airport. Very easy check in with a real person. The room was very clean and comfortable. Sinks were outside the toilet and shower. Sheets clean and crisp. Towels white and fluffy. Bed was a little hard. Pillows were large and fluffy. Very nice place to stay."

Reviewed on 18 Oct 2025

Rogue Regency Inn and Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
The price is ฿2,199 per night from 22 Oct to 23 Oct
฿2,199
฿2,452 total
22 Oct - 23 Oct
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,098 reviews)
"As a solo female traveller, I felt very safe at Flagship Inn! Thanks for a great stay!"

Reviewed on 15 Oct 2025

Flagship Inn of Ashland
See all 667 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 Travel Guide