Historic Downtown District, OR

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
Fully refundableReserve now, pay when you stay
The price is NT$3,048 per night from Mar 31 to Apr 1
NT$3,048
NT$3,894 total
Mar 31 - Apr 1
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! (1,006 reviews)
Everything was excellent

Reviewed on 2026/3/15

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 NT$3,472 per night from Apr 19 to Apr 20
NT$3,472
NT$3,871 total
Apr 19 - Apr 20
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! (1,000 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 2026/3/11

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 NT$6,757 per night from Mar 22 to Mar 23
NT$6,757
NT$7,952 total
Mar 22 - Mar 23
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 2026/1/15

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! (591 reviews)
Nice job on the room, service.

Reviewed on 2026/3/16

McCall House Boutique Inn
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is NT$4,628 per night from Mar 28 to Mar 29
NT$4,628
NT$5,161 total
Mar 28 - Mar 29
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! (1,713 reviews)
Enjoyed my stay

Reviewed on 2026/3/18

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is NT$2,758 per night from Mar 24 to Mar 25
NT$2,758
NT$3,262 total
Mar 24 - Mar 25
includes taxes & fees
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (2,883 reviews)
Clean room nice restaurant

Reviewed on 2026/3/19

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.

Other neighborhoods around Historic Downtown District

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

Historic Railroad District

4.5/5(7 area reviews)

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

4.5/5(12 area reviews)

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

5/5(1 area review)

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

Skidmore Academy Historic District


Historic Downtown District, OR