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

Oregon Shakespeare Festival

9.2/10 (620 reviews)
You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
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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$4,308 per night from Jul 5 to Jul 6
NT$4,308
NT$4,803 total
Jul 5 - Jul 6
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)
"Great location within a really short walking distance to the downtown area, restaurants and theaters. The pool was a nice bonus and the continental breakfast was perfectly adequate."

Reviewed on 2026/6/30

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$5,990 per night from Jul 26 to Jul 27
NT$5,990
NT$7,191 total
Jul 26 - Jul 27
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! (1,006 reviews)
"Loved the old hotel. Front desk people were very kind & helpful. Our room was small but well appointed & spotlessly clean. Location was ideal, right in the middle of Ashland. The Shakespeare theaters were a block away. We will stay again."

Reviewed on 2026/6/29

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is NT$8,397 per night from Jul 12 to Jul 13
NT$8,397
NT$10,055 total
Jul 12 - Jul 13
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 ...
Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
Fully refundable
The price is NT$7,914 per night from Jul 6 to Jul 7
NT$7,914
NT$8,824 total
Jul 6 - Jul 7
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! (600 reviews)
"McCall Boutique was an excellent stay! We will definitely be back for a return visit."

Reviewed on 2026/6/26

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$5,419 per night from Jul 4 to Jul 5
NT$5,419
NT$6,479 total
Jul 4 - Jul 5
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! (1,010 reviews)
"Couldn't recommend this place highly enough. Everything from the check-in to breakfast was perfect."

Reviewed on 2026/6/27

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$3,298 per night from Jul 5 to Jul 6
NT$3,298
NT$3,869 total
Jul 5 - Jul 6
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! (3,144 reviews)
"Staff made a great recommendation for evening dinner and a hike for a couple hours before noon. No coffee or water available in the lobby. Breakfast available at attached restaurant."

Reviewed on 2026/6/30

Rogue Regency Inn Medford Airport
See all 702 properties in Historic Downtown District
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.
A rusted metal bridge in a forested area.

Historic Railroad District

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

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

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

A town with buildings and trees in autumn colors, surrounded by mountains.

Skidmore Academy Historic District

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

Historic Downtown District, OR