Historic Downtown District, OR

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

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

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
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

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

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

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 entertainment choices.

Allen Elizabethan Theatre

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 entertainment choices and acclaimed theater scene.

Thomas 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 acclaimed theater scene.

Angus Bowmer Theatre

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
Rafting Kikacéki

Kikacéki (Ward's) Canyon

$250
per adult
Kikacéki (Ward's) Canyon
See all activities in Ashland

Historic Downtown District Hotel Deals

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
$159 nightly
The price is $177 total per night from Aug 24 to Aug 25
$177 total
Aug 24 - Aug 25
Total includes taxes and 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! (1,006 reviews)
Comfortable in Ashland
"The Bard's Inn is comfortable and welcoming, and an easy stroll down the street to restaurants, shops and the Oregon Shakespeare Festival shows"

Reviewed on Jul 28, 2025

The Bard's Inn, BW Signature Collection by Best Western
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St, Ashland, OR
$183 nightly
The price is $204 total per night from Aug 10 to Aug 11
$204 total
Aug 10 - Aug 11
Total includes taxes and 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! (1,009 reviews)
"Beautiful old hotel (refurbished) close to everything in Ashland!"

Reviewed on Jul 29, 2025

Ashland Springs Hotel
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
153 Oak St, Ashland, OR
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.8/10 Exceptional! (265 reviews)
"Great, friendly, helpful staff. Walk to the theater, gourmet breakfasts."

Reviewed on Jul 22, 2025

Get rates
McCall House Boutique Inn
Winchester Inn

Winchester Inn

3.5 out of 5
35 S. 2nd St., Ashland, OR
$228 nightly
The price is $255 total per night from Aug 4 to Aug 5
$255 total
Aug 4 - Aug 5
Total includes taxes and 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! (249 reviews)
"This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. ..."

Reviewed on Jul 23, 2025

Winchester Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $122 total per night from Jul 30 to Jul 31
$122 total
Jul 30 - Jul 31
Total includes taxes and 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! (2,193 reviews)
"Just passing through on way to Seattle from LA and this place was a nice place to rest for the night. Continental breakfast was good with lots of seating. I would recommend"

Reviewed on Jul 28, 2025

Rogue Regency Inn and Suites
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
$90 nightly
The price is $101 total per night from Aug 28 to Aug 29
$101 total
Aug 28 - Aug 29
Total includes taxes and fees
Book a stay at this spa hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,033 reviews)
"Easy to get to and from, coming from Central OR for a work trip. Resturant next door and close to meeting room. Staff were really friendly and helpful. Room was comfortable"

Reviewed on Jul 27, 2025

Quality Inn & Suites Medford Airport
See all 658 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
See our Where To Stay guide

Historic Downtown District, OR

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