Historic Downtown District
Ashland
Visit Historic Downtown District
Stay near popular Historic Downtown District attractions
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 S$194 per night from 22 Jun to 23 Jun
S$194
22 Jun - 23 Jun
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! (1,013 reviews)
"I made a mistake and did not reserve the type of room we usually get and the staff upgraded me for free. We frequently stay at Bards for the convenience of walking around down town and around Lithia Park. Great location!"
Reviewed on 12 Jun, 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is S$258 per night from 22 Jun to 23 Jun
S$258
22 Jun - 23 Jun
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! (1,011 reviews)
"The room was clean, beds comfortable, and staff friendly. The hotel is charming, and you couldn't ask for a better location -especially since we were seeing a performance at OCT, just a block away. We did breakfast, and while it was worth the $5 price tag, don't expect to be wowed. Pick up some coffee, ..."
Reviewed on 11 Jun, 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is S$447 per night from 6 Jul to 7 Jul
S$447
6 Jul - 7 Jul
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! (275 reviews)
"A lovely place to land. Beautiful Victorian with a garden to relax in. The room was so comfortable (even had a window seat) and the food was great. As was each member of the staff."
Reviewed on 2 May, 2026
McCall House Boutique Inn
153 Oak St Ashland OR
The price is S$394 per night from 6 Jul to 7 Jul
S$394
6 Jul - 7 Jul
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! (596 reviews)
"Perfection."
Reviewed on 27 May, 2026
Rogue Regency Inn Medford Airport
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is S$168 per night from 15 Jun to 16 Jun
S$168
15 Jun - 16 Jun
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. ...
8.8/10 Excellent! (3,108 reviews)
"The staff was fine They were very busy. We have stayed here before and it is getting run down—. Needs paint and a good cleaning. Breakfast was not the best. Beds were comfortable"
Reviewed on 13 Jun, 2026
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
The price is S$122 per night from 16 Jun to 17 Jun
S$122
16 Jun - 17 Jun
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! (1,361 reviews)
"Did not enjoy the virtual kiosk check-in experience."
Reviewed on 13 Jun, 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.
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.
