Historic Downtown District, OR

Ashland

Ashland is all about the Shakespeare down to the poppy #Red
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
This is the backside of the hotel where you park for free and enter conveniently from the 3rd floor
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.

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$2,467 per night from Feb 6 to Feb 7
NT$2,467
NT$3,224 total
Feb 6 - Feb 7
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)
Wonderful staff, great views, the rooms was clean with spa quality toiletries.

Reviewed on 2026/1/15

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$3,756 per night from Jan 25 to Jan 26
NT$3,756
NT$4,187 total
Jan 25 - Jan 26
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)
Clean, great location

Reviewed on 2026/1/12

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$5,582 per night from Jan 21 to Jan 22
NT$5,582
NT$6,601 total
Jan 21 - Jan 22
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! (267 reviews)
Property was beautiful. Room was large, clean and nicely appointed. The only disappointment was not getting to sample the highly rated breakfast as we learned after we made our booking that the kitchen and restaurant were shut down for a yearly deep clean.

Reviewed on 2026/1/4

Winchester Inn
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is NT$3,945 per night from Feb 1 to Feb 2
NT$3,945
NT$4,398 total
Feb 1 - Feb 2
includes taxes & fees
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 ...
9.8/10 Exceptional! (280 reviews)
Limited iptions for breafast

Reviewed on 2026/1/4

McCall House Boutique Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

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 a free airport shuttle. Our guests praise the breakfast and the ...
8.8/10 Excellent! (2,786 reviews)
Very friendly staff and comfortable room. We also enjoyed the breakfast.

Reviewed on 2026/1/20

Rogue Regency Inn and Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
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 ...
9.2/10 Wonderful! (1,637 reviews)
Great location in Ashland with a Safeway across the street.

Reviewed on 2026/1/16

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.

Other neighborhoods around Historic Downtown District

Road trip food!! I loved the burrito bowl

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
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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
Walked across the street from the ER and imagine this was the view from a physician parking lot

Skidmore Academy Historic District

5/5(1 area review)

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

Skidmore Academy Historic District


Historic Downtown District, OR