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 ...
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! (1,003 reviews)
"we appreciated the wonderful staff. Since the hotel is older, the one small elevator was the only way to avoid lots of stairs."
Reviewed on 20 Sept 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is ฿8,190 per night from 27 Sept to 28 Sept
฿8,190
฿9,830 total
27 Sept - 28 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! (287 reviews)
"Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely ..."
Reviewed on 5 Sept 2026
McCall House Boutique Inn
153 Oak St Ashland OR
The price is ฿10,616 per night from 17 Oct to 18 Oct
฿10,616
฿11,837 total
17 Oct - 18 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! (612 reviews)
"Breakfast was great each morning & they prepared a snack to go the last day, because we wanted to leave early."
Reviewed on 18 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 ...
9.6/10 Exceptional! (1,126 reviews)
"Matress was cozy. Great shower water pressure which to me is paramount. Cute Nice place next to small casino. The Restaurant was fun at night. Breakfast had real eggs!"
Reviewed on 19 Sept 2026
Red Lion Hotel Rogue Regency Medford Airport
2300 Biddle Rd Medford OR
The price is ฿3,087 per night from 22 Sept to 23 Sept
฿3,087
฿3,640 total
22 Sept - 23 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! (3,256 reviews)
"A/c did not function. No screen for only window at ground level. Broken furniture. Floor damaged. Surfaces not clean. Staff rude, cold and did not give basic information for stay. Would not recommend staying. Would recommend green lawn behind building for dogs."
Reviewed on 20 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.
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.
