Historic Downtown District

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 HK$745 per night from 24 Nov to 25 Nov
HK$745
HK$831 total
24 Nov - 25 Nov
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! (1,003 reviews)
"Love this place"

Reviewed on 5 Nov 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 HK$734 per night from 1 Dec to 2 Dec
HK$734
HK$940 total
1 Dec - 2 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
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is HK$1,048 per night from 9 Nov to 10 Nov
HK$1,048
HK$1,294 total
9 Nov - 10 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! (291 reviews)
"Amazing breakfasts, friendly staff, best location"

Reviewed on 10 Oct 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is HK$1,356 per night from 29 Nov to 30 Nov
HK$1,356
HK$1,511 total
29 Nov - 30 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
1907 Charmer, Perfect Downtown Location, So Clean!

1907 Charmer, Perfect Downtown Location, So Clean!

Ashland OR
Stay at this holiday home in Ashland. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Ashland Library and Oregon ...
9.4/10 Exceptional! (140 reviews)
"Love everything about this property. Very clean, accurately represented in the listing, communication could not have been easier or better. Host is very responsive to questions. We were able to park at the house and walk everywhere in this delightful town. Kitchen has everything needed. Beds are ..."

Reviewed on 22 Oct 2026

1907 Charmer, Perfect Downtown Location, So Clean!
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is HK$1,193 per night from 8 Nov to 9 Nov
HK$1,193
HK$1,437 total
8 Nov - 9 Nov
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
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