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 NT$2,760 per night from Mar 16 to Mar 17
NT$2,760
NT$3,554 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! (1,010 reviews)
Great location, comfortable room Larks restaurant is lovely.

Reviewed on 2026/3/8

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$3,461 per night from Mar 19 to Mar 20
NT$3,461
NT$3,859 total
Mar 19 - Mar 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! (1,003 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$7,256 per night from Mar 15 to Mar 16
NT$7,256
NT$8,523 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
Fully refundableReserve now, pay when you stay
The price is NT$4,287 per night from Mar 23 to Mar 24
NT$4,287
NT$4,780 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! (1,705 reviews)
Pet friendly, spotless room with a very comfortable bed. Coffee and microwave in the room and a very nice continental breakfast. What else could you want? We highly recommend Stratford Inn for a stay in Ashland.

Reviewed on 2026/3/11

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! (2,871 reviews)
ETA at airport was midnight. Shuttle was prompt. Older facilities but clean . Breakfast is typical...ok. Staff was brief/ polite.

Reviewed on 2026/3/11

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 Thomas 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