Skidmore Academy Historic District, OR

Ashland

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

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

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

Southern Oregon University

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's acclaimed theater scene and lively festivals.

Southern Oregon University

Lithia Park

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Lithia Park

Oregon Cabaret Theatre

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

Howard Prairie Lake

Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants.

Howard Prairie Lake

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
See all activities in Ashland

Skidmore Academy Historic District Hotel Deals

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn

3.5 out of 5
451 North Main Street, Ashland, OR
$260 nightly
The price is $290 total per night from Sep 4 to Sep 5
$290 total
Sep 4 - Sep 5
Total with taxes and fees
Stay at this 3.5-star B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Allen Elizabethan Theatre and Angus Bowmer ...
Abigail’s Bed & Breakfast Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
$108 nightly
The price is $122 total per night from Sep 3 to Sep 4
$122 total
Sep 3 - Sep 4
Total with 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! (2,165 reviews)
"Only thing was the lobby and elevator were super hot. Room temp was great though"

Reviewed on Aug 29, 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
$161 nightly
The price is $180 total per night from Sep 3 to Sep 4
$180 total
Sep 3 - Sep 4
Total with taxes and 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 ...
Ashland Hills Hotel & Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
$81 nightly
The price is $91 total per night from Sep 3 to Sep 4
$91 total
Sep 3 - Sep 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
Flagship Inn of Ashland
La Quinta Inn & Suites by Wyndham Central Point - Medford

La Quinta Inn & Suites by Wyndham Central Point - Medford

3 out of 5
1777 La Rue Dr, Central Point, OR
$113 nightly
The price is $127 total per night from Sep 4 to Sep 5
$127 total
Sep 4 - Sep 5
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Central Point. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Central Point - Medford
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd, Medford, OR
$113 nightly
The price is $127 total per night from Sep 16 to Sep 17
$127 total
Sep 16 - Sep 17
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Medford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
9/10 Wonderful! (1,387 reviews)
"I had a road trip from San Francisco to Seattle, My Place at Medford is a perfect place to stay. The price is great for the neat, clean and newer room. Highly recommended and you will not be disappointment."

Reviewed on Aug 28, 2025

My Place Hotel-Medford OR
See all 666 properties in Skidmore Academy Historic 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 Skidmore Academy Historic District

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Historic Downtown District

5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

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
See our Where To Stay guide

Skidmore Academy Historic District, OR

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