Historic Downtown District Travel Guide

Ashland

A paved pedestrian area with trees, a white building with a green awning, and a dog walking.
A building with a purple awning labeled "Caldera Tap House" and a sign with a beer mug illustration.
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.

Stay near popular Historic Downtown District attractions

Things to do


Top hotels in Historic Downtown District

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is ฿2,879 per night from 14 Dec to 15 Dec
฿2,879
฿3,735 total
14 Dec - 15 Dec
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
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 ฿2,818 per night from 9 Dec to 10 Dec
฿2,818
฿3,142 total
9 Dec - 10 Dec
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 ...
8.4/10 Very good! (1,004 reviews)
"The Bards Inn was close to all the fun shops, restaurants, and Lithia Park."

Reviewed on 6 Nov 2026

The Bard's Inn, BW Signature Collection by Best Western
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is ฿4,290 per night from 15 Nov to 16 Nov
฿4,290
฿5,314 total
15 Nov - 16 Nov
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! (292 reviews)
"Well maintained and beautiful Victorian boutique hotel located within a short walk to Main Street. Our room had all the modern amenities. Staff very helpful. Breakfast was good."

Reviewed on 10 Nov 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is ฿5,335 per night from 14 Nov to 15 Nov
฿5,335
฿5,949 total
14 Nov - 15 Nov
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
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is ฿3,233 per night from 15 Nov to 16 Nov
฿3,233
฿3,944 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,576 reviews)
"酒店设施很干净,尤其是卫生间。非常棒的体验"

Reviewed on 13 Nov 2026

Ashland Hills Hotel & Suites
Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is ฿2,991 per night from 14 Dec to 15 Dec
฿2,991
฿3,534 total
14 Dec - 15 Dec
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. ...
8.6/10 Excellent! (3,286 reviews)
"Staff are very helpful and professional people!"

Reviewed on 12 Nov 2026

Red Lion Hotel Rogue Regency 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.

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.

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.

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