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$5,451 per night from Aug 16 to Aug 17
NT$5,451
NT$6,078 total
Aug 16 - Aug 17
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! (1,017 reviews)
"Great location for sure! The room was a little out dated but it goes with the town I feel. Breakfast was good and easy hotel parking. Best part they allowed a late check-out at noon for no extra fee."

Reviewed on 2026/8/11

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$5,787 per night from Sep 13 to Sep 14
NT$5,787
NT$6,969 total
Sep 13 - Sep 14
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! (1,000 reviews)
"The room was small and the breakfast minimal, considering that the hotel included a $5 charge for breakfast. The elevator was slow, and housekeeping was only offered after 3 days in residence. It is an old hotel with small rooms and bathrooms. I can only recommend it as an alternative to other more ..."

Reviewed on 2026/8/11

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is NT$5,421 per night from Aug 16 to Aug 17
NT$5,421
NT$6,609 total
Aug 16 - Aug 17
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! (283 reviews)
"Everything was perfect"

Reviewed on 2026/8/6

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is NT$8,882 per night from Aug 31 to Sep 1
NT$8,882
NT$9,904 total
Aug 31 - Sep 1
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 ...
9.2/10 Wonderful! (604 reviews)
"Very nice stay and nice people:). Breakfast tasty with good amenities. Only issue was the bed was a bit uncomfy."

Reviewed on 2026/8/5

McCall House Boutique Inn
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is NT$5,076 per night from Aug 26 to Aug 27
NT$5,076
NT$6,098 total
Aug 26 - Aug 27
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 ...
9.6/10 Exceptional! (1,071 reviews)
"The hotel restaurant food/ bar was really good and prices great. It was close to the pool. We stayed for 4 nights so it would’ve been nice to have a little mix of the hot breakfast items besides the same thing. Also we didn’t have an ice machine on our floor. So that was kinda a pain to have to take ..."

Reviewed on 2026/8/12

Compass by Margaritaville in Medford
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is NT$3,032 per night from Sep 13 to Sep 14
NT$3,032
NT$3,573 total
Sep 13 - Sep 14
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 ...
8.8/10 Excellent! (3,189 reviews)
"Traveled from Washington to California on I5, so we stopped here for the night. The room was clean and comfortable. The free breakfast was good. The man who checked us in was very friendly, but not very helpful. Rather than volunteering the information, I had to ask the times and location for breakfast. ..."

Reviewed on 2026/8/13

Rogue Regency Inn Medford Airport
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 Allen Elizabethan Theatre and Thomas 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 Thomas Theatre are two attractions nearby that you can check out.



Historic Downtown District, OR