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
฿328
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 ฿4,632 per night from 18 Oct to 19 Oct
฿4,632
฿5,164 total
18 Oct - 19 Oct
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! (1,003 reviews)
"Friendly staff. Themed decor. Good location for OSF. Ridiculously small bed pillows. I stayed 2 nights. Staff came in to add new facecloths - but did not make the bed ….?"
Reviewed on 20 Sept 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is ฿5,693 per night from 18 Oct to 19 Oct
฿5,693
฿6,879 total
18 Oct - 19 Oct
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)
"It was close to the Shakespeare festival site. We had a great view. Breakfast was the same as the free breakfast at the hotel down the road. Air conditioning was good. There were big stains in several places on the carpet in our room."
Reviewed on 20 Sept 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is ฿6,508 per night from 28 Sept to 29 Sept
฿6,508
฿7,880 total
28 Sept - 29 Sept
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! (288 reviews)
"The property is very charming, and comfortable with beautiful gardens and outdoor spaces. The breakfast choices were delicious and dinner was also exceptional. Staff is very warm, friendly and helpful. I recommend highly."
Reviewed on 21 Sept 2026
McCall House Boutique Inn
153 Oak St Ashland OR
The price is ฿9,176 per night from 5 Oct to 6 Oct
฿9,176
฿10,232 total
5 Oct - 6 Oct
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! (613 reviews)
"Location location location! Very close to all the OSF facilities. Very close to lots of restaurants. Thoughtful staff and wonderful breakfast. We had to leave early our last morning and they prepared a take away breakfast. The furnishings are a little tired but everything else was excellent. We would ..."
Reviewed on 20 Sept 2026
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is ฿5,068 per night from 12 Oct to 13 Oct
฿5,068
฿6,101 total
12 Oct - 13 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 ...
Red Lion Hotel Rogue Regency Medford Airport
2300 Biddle Rd Medford OR
The price is ฿3,087 per night from 27 Sept to 28 Sept
฿3,087
฿3,640 total
27 Sept - 28 Sept
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! (3,261 reviews)
"The property is dated and needs to be upgraded. While we were there we noticed the one staff member trying to check in over 50 guests no one to help him people were waiting over an hour and a half to get checked in that's ridiculous."
Reviewed on 21 Sept 2026
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.
Check Historic Downtown District hotel availability
Where to stay in Historic Downtown District
Find the best Historic Downtown District areas for the activities you enjoy most.
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.
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.
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 Angus Bowmer Theatre.
