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

Things to do


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 ฿5,602 per night from 23 Aug to 24 Aug
฿5,602
฿6,246 total
23 Aug - 24 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 ...
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 ฿5,947 per night from 13 Sept to 14 Sept
฿5,947
฿7,162 total
13 Sept - 14 Sept
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 ฿5,956 per night from 23 Aug to 24 Aug
฿5,956
฿7,238 total
23 Aug - 24 Aug
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 ฿9,128 per night from 18 Aug to 19 Aug
฿9,128
฿10,177 total
18 Aug - 19 Aug
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 ...
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 ฿5,339 per night from 6 Sept to 7 Sept
฿5,339
฿6,404 total
6 Sept - 7 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 ...
9.6/10 Exceptional! (1,056 reviews)
"Great spot for youth sports"

Reviewed on 17 Aug 2026

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 ฿3,116 per night from 13 Sept to 14 Sept
฿3,116
฿3,671 total
13 Sept - 14 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. ...
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 for the activities you enjoy most.

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.

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.

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 Oregon Shakespeare Festival.



Historic Downtown District Travel Guide