Historic Downtown District, OR

Ashland

Landmark building in Ashland Oregon.
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.

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 ¥14,921 per night from Feb 27 to Feb 28
¥14,921
¥18,977 total
Feb 27 - Feb 28
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! (1,012 reviews)
Pros—-staff was incredibly kind Great food available for room service through Larks Cons—room was uncomfortably small.. luckily it was only one person but 2 people could not move around comfortably in this room and the bedding MUST be updated. We truly aren’t ones to complain but it might’ve been ...

Reviewed on Feb 23, 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 ¥13,898 per night from Feb 28 to Mar 1
¥13,898
¥15,496 total
Feb 28 - Mar 1
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)
The first time we stayed at The Bard's Inn back in 2020 was an amazing experience. The room was extremely nice, service was great, food was great. This time, though, the room was very dingy, with minimal amenities. It looked as though nothing had been done with it in years. The food experience was ...

Reviewed on Feb 17, 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 ¥27,987 per night from Feb 27 to Feb 28
¥27,987
¥33,080 total
Feb 27 - Feb 28
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
The price is ¥22,230 per night from Feb 27 to Feb 28
¥22,230
¥24,786 total
Feb 27 - Feb 28
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 ...
9.2/10 Wonderful! (588 reviews)
It was an amazing stay! Exceptional in every way. And the breakfast was a lovely bonus. Too notch

Reviewed on Feb 20, 2026

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! (2,854 reviews)
Clean room, pleasant staff. We needed parking for RV and they have a great lot for that. The breakfast is hit or miss. This time it was ok. The last time it was not. Some rooms have comfortable beds and others do not. We stay here only because of the RV parking

Reviewed on Feb 25, 2026

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 ...
9.4/10 Exceptional! (1,696 reviews)
Great room, clean but more importantly great mattress!!

Reviewed on Feb 25, 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.

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 Thomas Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District


Historic Downtown District, OR