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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Things to do

An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

￥1,595
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

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 ￥26,742 per night from Aug 23 to Aug 24
￥26,742
￥29,817 total
Aug 23 - Aug 24
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! (1,026 reviews)
"A very nice and comfy place. Staff were friendly and helpful. Location is great for downtown access. We enjoyed it!"

Reviewed on Aug 20, 2026

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 ￥28,391 per night from Sep 13 to Sep 14
￥28,391
￥34,191 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! (1,006 reviews)
"Location is good"

Reviewed on Aug 19, 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ￥26,907 per night from Aug 23 to Aug 24
￥26,907
￥32,783 total
Aug 23 - Aug 24
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 Aug 6, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ￥43,576 per night from Aug 23 to Aug 24
￥43,576
￥48,587 total
Aug 23 - Aug 24
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
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is ￥25,491 per night from Sep 6 to Sep 7
￥25,491
￥30,577 total
Sep 6 - Sep 7
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
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ￥14,876 per night from Sep 13 to Sep 14
￥14,876
￥17,527 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 ...
Rogue Regency Inn Medford Airport
See all 689 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 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 rusted metal bridge in a forested area.

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.

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 Thomas Theatre are two attractions nearby that you can check out.

Historic Downtown District, OR