Historic Downtown District

Ashland

Historic Downtown District
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts
Photo by Shannon Willitts

Popular places to visit

Oregon Shakespeare Festival

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
Mount Ashland Ski Area

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

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 entertainment choices.

Allen Elizabethan Theatre

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

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 entertainment choices.

Angus Bowmer Theatre

Thomas Theatre

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

Thomas Theatre

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

S$54
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

S$45
per traveller
Ashland Puzzling Adventure
See all activities in Ashland

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 S$300 per night from 23 Jun to 24 Jun
S$300
23 Jun - 24 Jun
includes taxes & fees
Stay at this 3-star 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! (1,002 reviews)
"If you like to travel back to a time when there was grand old hotels, then this is the place for you. Built in the 1920's, and standing nine stories tall, the interior and exterior architecture harkens back to what hotels use to look like."

Reviewed on 6 Jun, 2025

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 S$228 per night from 8 Jul to 9 Jul
S$228
8 Jul - 9 Jul
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! (1,001 reviews)
"Nothing fancy, but clean and comfortable. Can’t beat the location for walking to downtown, Lithia Park, shops, restaurants and, of course, the theaters. They even had an ev charger for our car, but after we charged it, we parked it and didn’t drive for the next 3 days."

Reviewed on 8 Jun, 2025

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 S$354 per night from 30 Jun to 1 Jul
S$354
30 Jun - 1 Jul
includes taxes & fees
Stay at this 3.5-star inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (245 reviews)
"quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention."

Reviewed on 16 May, 2025

Winchester Inn
Rogue Regency Inn and Suites
Rogue Regency Inn and Suites
3 out of 5
2300 Biddle Rd, Medford, OR
The price is S$156 per night from 16 Jun to 17 Jun
S$156
16 Jun - 17 Jun
includes taxes & fees
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! (1,995 reviews)
"Great place to stay when traveling with your pet. We have stayed before they switched from a sit down breakfast service to a pretty limited grab and go but it does include a hot breakfast sandwich. I am a vegetarian and my options were pretty slim I wish there was a egg and cheese option."

Reviewed on 9 Jun, 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is S$194 per night from 15 Jun to 16 Jun
S$194
15 Jun - 16 Jun
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,428 reviews)
"Very kind and patient with me. Great customer service!"

Reviewed on 9 Jun, 2025

Ashland Hills Hotel & Suites
Ramada by Wyndham Medford Airport North
Ramada by Wyndham Medford Airport North
2 out of 5
2111 Biddle Rd, Medford, OR
The price is S$103 per night from 24 Jun to 25 Jun
S$103
24 Jun - 25 Jun
includes taxes & fees
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 ...
7.4/10 Good! (883 reviews)
"It seemed oddly located. No lawn or landscaping."

Reviewed on 9 Jun, 2025

Ramada by Wyndham Medford Airport North
See all 653 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