Historic Downtown District

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
This is the backside of the hotel where you park for free and enter conveniently from the 3rd floor

Popular places to visit

Things to do


Top hotels in Historic Downtown District

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is P4,602 per night from Feb 6 to Feb 7
P4,602
P6,015 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! (1,000 reviews)
We upgraded and that was not wise. The rooms are extremely small. The upgrade was not worth the $ as we viewed 3 rooms before choosing one. The Hotel is a classic, historical center of quaint Ashland. Good staffstaff

Reviewed on Jan 27, 2026

Ashland Springs Hotel
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St. Ashland OR
The price is P14,827 per night from Feb 4 to Feb 5
P14,827
P17,382 total
Feb 4 - Feb 5
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
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 P6,185 per night from Feb 11 to Feb 12
P6,185
P6,896 total
Feb 11 - Feb 12
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 Jan 12, 2026

The Bard's Inn, BW Signature Collection by Best Western
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St Ashland OR
The price is P7,750 per night from Feb 5 to Feb 6
P7,750
P8,641 total
Feb 5 - Feb 6
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! (283 reviews)
Absolutely beautiful hotel. Our stay was wonderful!

Reviewed on Jan 31, 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! (2,802 reviews)
Front desk was exceptional. Great stay.

Reviewed on Jan 28, 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 ...
9.2/10 Wonderful! (1,669 reviews)
Great location and easily walkable to anything and everything downtown!

Reviewed on Feb 1, 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 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 Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

Skidmore Academy Historic District


Historic Downtown District