Historic Downtown District Travel Guide
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 £100 per night from 4 Nov to 5 Nov
£100
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 ...
Ashland Springs Hotel
212 E Main St Ashland OR
The price is £90 per night from 11 Nov to 12 Nov
£90
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. ...
9.2/10 Wonderful! (1,002 reviews)
"The staff was friendly and very helpful."
Reviewed on 18 Oct 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is £124 per night from 26 Oct to 27 Oct
£124
26 Oct - 27 Oct
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 £130 per night from 18 Nov to 19 Nov
£130
18 Nov - 19 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 £82 per night from 20 Oct to 21 Oct
£82
20 Oct - 21 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. ...
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is £127 per night from 26 Oct to 27 Oct
£127
26 Oct - 27 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! (1,169 reviews)
"The staff was fantastic, very pleasant. We did find a pile of dirty towels in the closet that had been missed when the room was cleaned, but other than that it was a very nice, clean room."
Reviewed on 18 Oct 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.
