Historic Downtown District Travel Guide
Ashland
Visit Historic Downtown District
Stay near popular Historic Downtown District attractions
Things to do
The Cultural Heart of Ashland: A Self-Guided Audio Tour
฿334
per adult
Top hotels in Historic Downtown District
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
The price is ฿3,989 per night from 4 Nov to 5 Nov
฿3,989
฿4,447 total
4 Nov - 5 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 ...
8.4/10 Very good! (1,003 reviews)
"The room was clean and the bed was comfortable. However, the pillows are in dire need for an upgrade. And the bathroom could use a renovation. The hotel is very convenient for attending the theater at the Shakespeare Festival, and is also a short walk to all of the area restaurants. In addition, ..."
Reviewed on 14 Oct 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is ฿3,136 per night from 11 Nov to 12 Nov
฿3,136
฿4,018 total
11 Nov - 12 Nov
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. ...
Winchester Inn
35 S. 2nd St. Ashland OR
The price is ฿4,377 per night from 16 Nov to 17 Nov
฿4,377
฿5,411 total
16 Nov - 17 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! (291 reviews)
"Amazing breakfasts, friendly staff, best location"
Reviewed on 10 Oct 2026
McCall House Boutique Inn
153 Oak St Ashland OR
Fully refundable
The price is ฿5,791 per night from 2 Nov to 3 Nov
฿5,791
฿6,457 total
2 Nov - 3 Nov
includes taxes & fees
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 ...
9.2/10 Wonderful! (618 reviews)
"Our favorite hotel In Ashland. It is probably the most beautiful building in Ashland and the rooms and the amenities are first class. We recommend this place to everyone."
Reviewed on 13 Oct 2026
Red Lion Hotel Rogue Regency Medford Airport
2300 Biddle Rd Medford OR
The price is ฿3,105 per night from 18 Oct to 19 Oct
฿3,105
฿3,661 total
18 Oct - 19 Oct
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.6/10 Excellent! (3,286 reviews)
"Need maintenance"
Reviewed on 16 Oct 2026
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is ฿4,736 per night from 18 Oct to 19 Oct
฿4,736
฿5,732 total
18 Oct - 19 Oct
includes taxes & fees
Stay at this golf hotel in Medford. Enjoy free breakfast, free parking and a casino. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
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.
Where to stay in Historic Downtown District
Find the best Historic Downtown District areas for the activities you enjoy most.
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.
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.
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.
