Historic Downtown District, OR

Ashland
Historic Downtown District

Popular places to visit

Image for Oregon Shakespeare Festival

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.

Oregon Shakespeare Festival
Image for Mount Ashland Ski Area

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.

Mount Ashland Ski Area
Image for Oregon Cabaret Theatre

Oregon Cabaret Theatre

4.5/5(47 reviews)

You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

Oregon Cabaret Theatre
Image for Allen Elizabethan Theatre

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.

Allen Elizabethan Theatre
Image for Angus Bowmer Theatre

Angus Bowmer Theatre

You can get tickets for a performance at Angus Bowmer Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its lively festivals.

Angus Bowmer Theatre
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Thomas Theatre

4.5/5(81 reviews)

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices.

Thomas Theatre

Historic Downtown District Hotel Deals

Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is ￥17,423 per night from Jun 6 to Jun 7
￥17,423
per night
Jun 6 - Jun 7
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,164 reviews)
"I like everything about this hotel. Stay here when ever I’m in Medford."

Reviewed on Jun 4, 2024

Rogue Regency Inn and Suites
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
The price is ￥36,111 per night from Jun 16 to Jun 17
￥36,111
per night
Jun 16 - Jun 17
Stay at this 3-star spa hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,002 reviews)
"It is an extremely lovely and exceptionally well maintained hotel. Our room was small, but we did get the most reasonably priced room! The room had a nice modern bathroom. Everything was perfectly clean. They have a secure parking garage."

Reviewed on May 28, 2024

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
Fully refundableReserve now, pay when you stay
The price is ￥29,425 per night from Jun 10 to Jun 11
￥29,425
per night
Jun 10 - Jun 11
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 ...
8.8/10 Excellent! (1,003 reviews)
"A very clean, comfortable and convenient place to stay"

Reviewed on Jun 3, 2024

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
Fully refundable
The price is ￥35,572 per night from Jun 10 to Jun 11
￥35,572
per night
Jun 10 - Jun 11
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan ...
9.8/10 Exceptional! (233 reviews)
Good place to stay in Ashland.
"Nice place, well located, great staff, delightful breakfast. Like many older inns, room was pretty small and the electrical system would benefit from some modernizing to accommodate needs of 2020+ info tech. However, they did offer EV charging, which was a real plus."

Reviewed on May 24, 2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is ￥28,826 per night from Jun 9 to Jun 10
￥28,826
per night
Jun 9 - Jun 10
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (204 reviews)
"This was a lovely stopover in Ashland on our way to Santa Barbara. It is a charming, well run inn. This was Memorial Day weekend so breakfast was not “full service” but what we had was delicious."

Reviewed on Jun 3, 2024

Winchester 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 ￥19,359 per night from Jun 10 to Jun 11
￥19,359
per night
Jun 10 - Jun 11
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,522 reviews)
"The Stratford Inn provided a convenient stay for our visit to Ashland. The hotel is a convenient walk to Lithia Park and downtown with plenty of options for dining close by. My family enjoyed are stay and look forward to visiting again"

Reviewed on May 31, 2024

Stratford Inn
See all 590 properties in Historic Downtown District
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