Historic Downtown District

Ashland

Landmark building in Ashland Oregon.
Ashland is all about the Shakespeare down to the poppy #Red
We had a corner queen on the 8th floor and this is a close look at the neoclassical gothic architecture from our bedroom window
I always check out the local chamber of commerce when I land in a town I haven’t been to before.  Ashland Oregon Chamber of Commerce is unique in that it’s beside this amazing bronze Shakespeare statue.
Enjoyed getting to see a screening of Agatha Christie’s “Murder on the Orient Express in this classic old movie theater

Popular places to visit


Historic Downtown District Hotel Deals

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is CA $119 per night from Mar 16 to Mar 17
CA $119
CA $153 total
Mar 16 - Mar 17
includes taxes & fees
Book a stay at this spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,003 reviews)
Staff was friendly. The room was neat and clean. Very good location. It would be nice to have coffee and tea available in the beautiful lobby.

Reviewed on Mar 12, 2026

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 CA $157 per night from Mar 16 to Mar 17
CA $157
CA $175 total
Mar 16 - Mar 17
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,003 reviews)
Heater roared all night. Beds were adequate. Weirdly there was a mini fridge but no microwave. "kid" who checked us in def was not into his job, didn't really explain much of anything. The woman who was on duty in the morning was much more personable. Price ok for a three star motel.

Reviewed on Mar 11, 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 CA $277 per night from Mar 15 to Mar 16
CA $277
CA $327 total
Mar 15 - Mar 16
includes taxes & fees
Stay at this inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oregon ...
9.6/10 Exceptional! (270 reviews)
The room is fantastic!! Highly recommend!

Reviewed on Jan 15, 2026

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (590 reviews)
Room clean, great breakfast

Reviewed on Mar 1, 2026

McCall House Boutique Inn
Spacious 2 bedroom historic home with two king beds and kitchenette.

Spacious 2 bedroom historic home with two king beds and kitchenette.

Ashland OR
The price is CA $271 per night from Apr 7 to Apr 8
CA $271
CA $540 total
Apr 7 - Apr 8
includes taxes & fees
Stay at this apartment in Ashland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Allen Elizabethan Theatre and Angus Bowmer ...
10/10 Exceptional! (3 reviews)
Excellent location
Great location, nice place to stay. Could use a frying pan.

Reviewed on Apr 22, 2025

Spacious 2 bedroom historic home with two king beds and kitchenette.
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is CA $184 per night from Mar 23 to Mar 24
CA $184
CA $205 total
Mar 23 - Mar 24
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,706 reviews)
Love this place !!!!

Reviewed on Mar 12, 2026

Stratford Inn
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.

The Annual Vacation Sale

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Other neighbourhoods around Historic Downtown District

Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

Historic Railroad District
Street scene in downtown Ashland Oregon state.

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Siskiyou-Hargadine Historic District
Aerial view of Ashland, Oregon

Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Thomas Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District


Historic Downtown District

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