Historic Downtown District Travel Guide

Tourist Guide

Historic Downtown District
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts

Popular places to visit

Activities


Our pick of the best Historic Downtown District Hotel Deals

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 AU$207 per night from 1 Dec to 2 Dec
AU$207
1 Dec - 2 Dec
includes taxes & fees
Stay at this 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 reviews. ...
9.2/10 Wonderful! (1,004 reviews)
Front desk staff made me feel welcome and were very helpful!!!

Reviewed on 18 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
The price is AU$181 per night from 4 Dec to 5 Dec
AU$181
4 Dec - 5 Dec
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! (1,004 reviews)
The room was a little small for two king beds but was otherwise clean and comfortable. The staff was great. The hotels is convenient location to downtown Ashland is a big plus.

Reviewed on 20 Nov 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 AU$407 per night from 26 Nov to 27 Nov
AU$407
26 Nov - 27 Nov
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (258 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
Stay at this 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. Popular ...
9.8/10 Exceptional! (276 reviews)
The room and the breakfast. The staff were very nice.

Reviewed on 23 Nov 2025

McCall House Boutique Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
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! (2,630 reviews)
Quite nice, will come again!

Reviewed on 23 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 AU$89 per night from 5 Dec to 6 Dec
AU$89
5 Dec - 6 Dec
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! (1,167 reviews)
Clean rooms, friendly staff

Reviewed on 24 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 Shakespeare Festival and Lithia Park 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 Oregon Shakespeare Festival and Allen Elizabethan Theatre.

Skidmore Academy Historic District


Historic Downtown District Travel Guide

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