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

Popular places to visit


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 ฿3,464 per night from 10 Nov to 11 Nov
฿3,464
฿4,351 total
10 Nov - 11 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! (1,012 reviews)
Great location

Reviewed on 2 Nov 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 ฿3,218 per night from 15 Nov to 16 Nov
฿3,218
฿3,588 total
15 Nov - 16 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! (1,009 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 ฿6,199 per night from 9 Nov to 10 Nov
฿6,199
฿7,315 total
9 Nov - 10 Nov
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! (256 reviews)
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on 26 Oct 2025

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
The price is ฿5,900 per night from 6 Nov to 7 Nov
฿5,900
฿6,579 total
6 Nov - 7 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)
McCall House is A-plus!
Breakfast was great! Convenient location…walked to shopping, dinner, and a play.

Reviewed on 24 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 ฿3,071 per night from 13 Nov to 14 Nov
฿3,071
฿3,455 total
13 Nov - 14 Nov
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! (2,574 reviews)
Friendly check in staff

Reviewed on 5 Nov 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 ฿1,759 per night from 6 Nov to 7 Nov
฿1,759
฿1,961 total
6 Nov - 7 Nov
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! (1,127 reviews)
Easy check in, convenient location.

Reviewed on 1 Nov 2025

Flagship Inn of Ashland
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