Historic Downtown District, OR

Ashland

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.
A display window with a large red flower and a sign reading "Oregon Shakespeare Festival Welcome Center".
A building corner with ornate architectural details and arched windows overlooking a cityscape.
A detailed bronze sculpture of a group of people, some with raised hands, against a tiled wall.
A street with a 'NO PARKING' sign, a 'VARNS' sign, and a 'JEWEL BOX' storefront.

Stay near popular Historic Downtown District attractions


Historic Downtown District Hotel Deals

The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
The price is NT$4,113 per night from Nov 1 to Nov 2
NT$4,113
NT$4,587 total
Nov 1 - Nov 2
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,006 reviews)
"We liked the convenience of being in town. We were comfortable and felt safe. We liked having breakfast. The rooms needed updating…new lighting…the comforters need to be replaced. Smart TVs with streaming options. We definitely stay again."

Reviewed on 2026/10/7

The Bard's Inn, BW Signature Collection by Best Western
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is NT$2,712 per night from Nov 1 to Nov 2
NT$2,712
NT$3,518 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,003 reviews)
"The room was fine, older but updated. The only thing we would skip is the $5 breakfast voucher, would have rather gone out for breakfast."

Reviewed on 2026/10/7

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is NT$4,152 per night from Oct 26 to Oct 27
NT$4,152
NT$5,132 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (290 reviews)
"This inn is very sweet - and so well located. The room was spacious enough and the cooked breakfast option was a total highlight. The rooms, I said"

Reviewed on 2026/10/6

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is NT$5,510 per night from Nov 2 to Nov 3
NT$5,510
NT$6,143 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
McCall House Boutique Inn
Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is NT$2,945 per night from Nov 3 to Nov 4
NT$2,945
NT$3,473 total
Nov 3 - Nov 4
includes taxes & fees
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Red Lion Hotel Rogue Regency Medford Airport
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
The price is NT$4,835 per night from Oct 12 to Oct 13
NT$4,835
NT$5,821 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this golf hotel in Medford. Enjoy free breakfast, free parking, and a casino. Our guests praise the breakfast and the pool in our reviews. Popular ...
Compass by Margaritaville in Medford
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 and neighborhoods for the activities you enjoy most.

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.



Historic Downtown District, OR