Historic Downtown District Vacations
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Where to stay in Historic Downtown District
Find the best Historic Downtown District areas and neighborhoods for the activities you enjoy most. Learn more about Historic Downtown District
Historic Railroad District
4.5/5(7 area reviews)
Historic Railroad District might not have many top sights, but Ashland Library and Oregon Cabaret Theatre are two attractions nearby that you can check out.
Historic Downtown District Hotel Deals
Ashland Springs Hotel
212 E Main St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is SAR 582 per night from Apr 29 to Apr 30
SAR 582
SAR 668 total
includes taxes & fees
29 Apr - 30 Apr
9.2/10 Wonderful! (1,002 reviews)
"The Ashland Springs is an absolutely delightful historic Inn that has been lovingly cared for and where the staff is always helpful, attentive and generous. History is evident at every turn and the landmark designation is told in pictures and stories. A thoughtful breakfast area was a cheerful surprise ..."
Reviewed on 23 April 2025
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is SAR 506 per night from Apr 30 to May 1
SAR 506
SAR 565 total
includes taxes & fees
30 Apr - 1 May
8.6/10 Excellent! (1,002 reviews)
"Working walking distance of LIthia Park, shops and restaurants. Clean, comfortable room"
Reviewed on 25 April 2025
Winchester Inn
35 S. 2nd St., Ashland, OR
The price is SAR 908 per night from May 5 to May 6
SAR 908
SAR 1,062 total
includes taxes & fees
5 May - 6 May
9.6/10 Exceptional! (243 reviews)
"Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable."
Reviewed on 21 April 2025
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.
Discover the most popular places to visit in Historic Downtown District
Oregon Shakespeare Festival
4.5/5(265 reviews)
You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
Mount Ashland Ski Area
4/5(70 reviews)
Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.
Allen Elizabethan Theatre
You can enjoy a show at Allen Elizabethan Theatre during your stay in Ashland. Wander around the area's picturesque gardens or experience its acclaimed theater scene.