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
฿334
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 ฿5,695 per night from 27 Jul to 28 Jul
฿5,695
฿6,350 total
27 Jul - 28 Jul
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! (1,012 reviews)
"Older building with not quite enough parking.. Soundproofing between rooms and floor above not up to today's standards. Airi conditioner very noisy. Location is good to old town. Perhaps $50.00 a night more expensive than I would expect."
Reviewed on 25 Jul 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is ฿6,183 per night from 27 Jul to 28 Jul
฿6,183
฿7,435 total
27 Jul - 28 Jul
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. ...
9.4/10 Exceptional! (1,007 reviews)
"Quaint historical hotel right downtown and next to the theatres. Good restaurant."
Reviewed on 25 Jul 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is ฿5,664 per night from 27 Jul to 28 Jul
฿5,664
฿6,904 total
27 Jul - 28 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! (280 reviews)
"Good location. Good breakfast"
Reviewed on 14 Jul 2026
McCall House Boutique Inn
153 Oak St Ashland OR
The price is ฿9,279 per night from 27 Jul to 28 Jul
฿9,279
฿10,346 total
27 Jul - 28 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! (601 reviews)
"McCall Boutique was an excellent stay! We will definitely be back for a return visit."
Reviewed on 26 Jun 2026
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
The price is ฿5,731 per night from 4 Aug to 5 Aug
฿5,731
฿6,852 total
4 Aug - 5 Aug
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! (1,041 reviews)
"Nice new hotel"
Reviewed on 25 Jul 2026
Rogue Regency Inn Medford Airport
2300 Biddle Rd Medford OR
The price is ฿3,245 per night from 26 Jul to 27 Jul
฿3,245
฿3,819 total
26 Jul - 27 Jul
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.
Historic Railroad District
While Historic Railroad District isn't home to many top sights, Angus Bowmer Theatre and Oregon Shakespeare Festival 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 Angus Bowmer Theatre and Oregon Shakespeare Festival.
