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 ฿3,343 per night from 26 Nov to 27 Nov
฿3,343
฿3,727 total
26 Nov - 27 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 ...
8.4/10 Very good! (1,012 reviews)
"We booked Jere because everything else was taken that was in downtown. The hotel is ok. Breakfast was decent with some variety in terms of protein and fresh fruit. The tvs are out dated so we couldn’t watch Netflix and the property is spread out over 4 buildings at 3 different intersections."
Reviewed on 26 Oct 2026
Ashland Springs Hotel
212 E Main St Ashland OR
The price is ฿3,160 per night from 17 Nov to 18 Nov
฿3,160
฿4,047 total
17 Nov - 18 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! (1,003 reviews)
"The property is rather dated. There is a lack of outlets in the room for digital devices. My suggestion is that the bedside lamps should be replaced with lamps that have additional outlets and USB ports."
Reviewed on 24 Oct 2026
Winchester Inn
35 S. 2nd St. Ashland OR
The price is ฿4,510 per night from 9 Nov to 10 Nov
฿4,510
฿5,567 total
9 Nov - 10 Nov
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
The price is ฿5,728 per night from 1 Nov to 2 Nov
฿5,728
฿6,387 total
1 Nov - 2 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
Compass by Margaritaville in Medford
2399 S Pacific Hwy Medford OR
The price is ฿5,136 per night from 1 Nov to 2 Nov
฿5,136
฿6,183 total
1 Nov - 2 Nov
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! (1,185 reviews)
"The staff was super friendly. The water pressure for the shower was terrible."
Reviewed on 25 Oct 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is ฿3,312 per night from 19 Nov to 20 Nov
฿3,312
฿4,031 total
19 Nov - 20 Nov
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,567 reviews)
"Places was super clean, staff was nice, restaurant in hotel closes early around 9pm"
Reviewed on 24 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.
Check Historic Downtown District hotel availability
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.
