Historic Downtown District
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
S$13
per adult
Top hotels in Historic Downtown District
Ashland Springs Hotel
212 E Main St Ashland OR
The price is S$274 per night from 12 Oct to 13 Oct
S$274
12 Oct - 13 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. ...
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
The price is S$239 per night from 13 Sept to 14 Sept
S$239
13 Sept - 14 Sept
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)
"We stayed at the “London” property. The staff was quick to respond to a plumbing problem that we found upon arrival - no complaints there. The lobby and breakfast areas were fine. Our room was dark, however, the air conditioner noisy, and overall, it felt shabby and old. Could definitely use an ..."
Reviewed on 12 Sept, 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is S$309 per night from 20 Sept to 21 Sept
S$309
20 Sept - 21 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 S$389 per night from 14 Sept to 15 Sept
S$389
14 Sept - 15 Sept
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 ...
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is S$232 per night from 12 Oct to 13 Oct
S$232
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 S$138 per night from 13 Sept to 14 Sept
S$138
13 Sept - 14 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. ...
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 Oregon Shakespeare Festival.
