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
The price is NT$2,783 per night from Mar 16 to Mar 17
NT$2,783
NT$3,583 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 2026/3/12

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$3,682 per night from Apr 1 to Apr 2
NT$3,682
NT$4,106 total
Apr 1 - Apr 2
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$6,794 per night from Mar 15 to Mar 16
NT$6,794
NT$7,994 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 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! (590 reviews)
Room clean, great breakfast

Reviewed on 2026/3/1

McCall House Boutique Inn
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is NT$4,322 per night from Mar 23 to Mar 24
NT$4,322
NT$4,820 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! (1,707 reviews)
Clean, friendly staff, delightful stay.

Reviewed on 2026/3/13

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
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! (2,874 reviews)
My favorite place to stay

Reviewed on 2026/3/12

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