Historic Downtown District Travel Guide

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 get tickets for a performance 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

Rp178.431
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

Top hotels in Historic Downtown District

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 Rp2.995.026 per night from 30 Aug to 31 Aug
Rp2.995.026
Rp3.339.455 total
30 Aug - 31 Aug
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 ...
8.6/10 Excellent! (1,031 reviews)
"The property location is really convenient and walkable to the park and downtown! The furnishings are dated and a bit rundown. Staff was friendly and helpful. Continental breakfast was lackluster. Overall, an easy one night/quick stay for convenience."

Reviewed on 23 Aug 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 Rp3.407.571 per night from 30 Aug to 31 Aug
Rp3.407.571
Rp4.084.691 total
30 Aug - 31 Aug
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. ...
Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is Rp4.007.479 per night from 7 Sept to 8 Sept
Rp4.007.479
Rp4.824.354 total
7 Sept - 8 Sept
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! (283 reviews)
"Everything was perfect"

Reviewed on 6 Aug 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is Rp4.880.363 per night from 7 Sept to 8 Sept
Rp4.880.363
Rp5.441.605 total
7 Sept - 8 Sept
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! (607 reviews)
"A beautiful, comfortable and very convenient place to stay."

Reviewed on 24 Aug 2026

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 Rp2.789.037 per night from 31 Aug to 1 Sept
Rp2.789.037
Rp3.350.320 total
31 Aug - 1 Sept
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 ...
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 Rp1.706.532 per night from 7 Sept to 8 Sept
Rp1.706.532
Rp2.008.453 total
7 Sept - 8 Sept
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.8/10 Excellent! (3,245 reviews)
"Having a restaurant and bar in the building was very convenient. The breakfast was average, nothing special. Our bathroom has wallpaper that was peeling down, the shower rod prevented the curtain from covering the length of the tub, so water got all over the floor. Our room was large, clean and comfortable ..."

Reviewed on 25 Aug 2026

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 for the activities you enjoy most.
A tree-lined street with a mountain backdrop.

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.

A rusted metal bridge in a forested area.

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.

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

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 Thomas Theatre.

Historic Downtown District Travel Guide