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 Rp3.056.208 per night from 2 Aug to 3 Aug
Rp3.056.208
Rp3.407.741 total
2 Aug - 3 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! (1,017 reviews)
"We stayed in the older part of the hotel last week on our way up to Portland (See previous review). This time we had a newer building which was much lighter and larger with bigger windows. Unfortunately it had the same shiny and slippy comforters that slid off the bed and a very noisy a/c. We reported ..."

Reviewed on 29 Jul 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 Rp3.399.966 per night from 24 Aug to 25 Aug
Rp3.399.966
Rp4.081.514 total
24 Aug - 25 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. ...
9.2/10 Wonderful! (1,013 reviews)
"Good AC and great staff. Excellent location for plays. Larks is superb."

Reviewed on 28 Jul 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is Rp3.304.040 per night from 3 Aug to 4 Aug
Rp3.304.040
Rp4.012.211 total
3 Aug - 4 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 ...
Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is Rp4.959.679 per night from 18 Aug to 19 Aug
Rp4.959.679
Rp5.530.042 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 ...
9.2/10 Wonderful! (602 reviews)
"Staff was great!"

Reviewed on 27 Jul 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 Rp3.075.918 per night from 2 Aug to 3 Aug
Rp3.075.918
Rp3.677.404 total
2 Aug - 3 Aug
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 Rp1.766.683 per night from 13 Aug to 14 Aug
Rp1.766.683
Rp2.077.518 total
13 Aug - 14 Aug
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! (3,170 reviews)
"Good value hotel. Very convenient to/from freeway"

Reviewed on 28 Jul 2026

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, Angus Bowmer Theatre and Oregon Shakespeare Festival 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 Angus Bowmer Theatre and Oregon Shakespeare Festival.



Historic Downtown District Travel Guide