Historic Downtown District Travel Guide

Tourist Guide
Historic Downtown District

Popular places to visit

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Oregon Shakespeare Festival

You can get tickets for a performance 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
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Mount Ashland Ski Area

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
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Oregon Cabaret Theatre

You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.

Oregon Cabaret Theatre
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Allen Elizabethan Theatre

You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its lively festivals.

Allen Elizabethan Theatre
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Angus Bowmer Theatre

You can make plans for a show 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

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

Thomas Theatre

Our pick of the best 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 NZ$207 per night from 28 May to 29 May
NZ$207
per night
28 May - 29 May
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! (1,148 reviews)
Rogue Regency Inn and Suites, Medford, Oregon
"We had a very nice stay at the Rogue Regency Inn and Suites. It was great to have 2 options for meals at this locations so we did not have to go out somewhere else. Staff was very friendly, rooms were clean and beds were comfortable."

Reviewed on 24 May 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 NZ$425 per night from 2 Jun to 3 Jun
NZ$425
per night
2 Jun - 3 Jun
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! (1,008 reviews)
"Just a one night stay, but the historical nature of the building (despite small rooms) was wonderful. The guests were so kind to my puppy! Great hotel"

Reviewed on 26 May 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
The price is NZ$328 per night from 28 May to 29 May
NZ$328
per night
28 May - 29 May
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)
"The hotel is well located to visit the Shakespeare festival and restaurants. Check in would be made easier by giving parking directions before are since the hotel is located in 3 different buildings on different roads. Breakfast was disappointing. There was no fresh fruit. Pork with no other meat ..."

Reviewed on 25 May 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
The price is NZ$338 per night from 28 May to 29 May
NZ$338
per night
28 May - 29 May
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 24 May 2024

McCall House Boutique Inn
Winchester Inn
Winchester Inn
3.5 out of 5
35 S. 2nd St., Ashland, OR
The price is NZ$385 per night from 3 Jun to 4 Jun
NZ$385
per night
3 Jun - 4 Jun
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! (203 reviews)
"The service was delightful"

Reviewed on 12 May 2024

Winchester Inn
My Place Hotel-Medford OR
My Place Hotel-Medford OR
3 out of 5
580 Airport Rd, Medford, OR
The price is NZ$213 per night from 2 Jun to 3 Jun
NZ$213
per night
2 Jun - 3 Jun
Stay at this 3-star business-friendly hotel in Medford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (887 reviews)
"."

Reviewed on 25 May 2024

My Place Hotel-Medford OR
See all 593 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 neighbourhoods around Historic Downtown District

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Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Historic Railroad District
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Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Siskiyou-Hargadine Historic District
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Skidmore Academy Historic District

While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

Skidmore Academy Historic District

Historic Downtown District Travel Guide

Choose two or more items and save on your trip: