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 lively festivals 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 entertainment choices 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 acclaimed theater scene 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

￥5,189
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
The price is ￥38,467 per night from Sep 28 to Sep 29
￥38,467
￥42,891 total
Sep 28 - Sep 29
includes taxes & 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 ...
9.6/10 Exceptional! (42 reviews)
Abigail's B & B
"Abigail's is a lovely B & B and the hosts are quite accommodating. We felt very welcome in their home and were provided several amenities including a blanket and seat cushions for the play we attended in the outdoor Elizabethan Theatre."

Reviewed on Jul 14, 2025

Abigail’s Bed & Breakfast Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
The price is ￥15,979 per night from Sep 24 to Sep 25
￥15,979
￥17,976 total
Sep 24 - Sep 25
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! (2,419 reviews)
"Elevators are only on 1 end of the entire complex"

Reviewed on Sep 18, 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is ￥18,664 per night from Sep 28 to Sep 29
￥18,664
￥22,291 total
Sep 28 - Sep 29
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! (1,467 reviews)
Nice hotel in Ashland
"Cute, clean hotel right off of I-5. Easy to find. Friendly staff and nice grounds"

Reviewed on Sep 18, 2025

Ashland Hills Hotel & Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
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 ...
8.8/10 Excellent! (1,030 reviews)
"University campus right across the street. Place to charge an electric car near the student dining hall within walking distance. Free Charge Point station."

Reviewed on Sep 19, 2025

Get rates
Flagship Inn of Ashland
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
The price is ￥12,324 per night from Oct 19 to Oct 20
￥12,324
￥13,935 total
Oct 19 - Oct 20
includes taxes & 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! (1,011 reviews)
"The location to the airport."

Reviewed on Sep 19, 2025

Quality Inn & Suites Medford Airport
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd, Medford, OR
The price is ￥13,913 per night from Oct 4 to Oct 5
￥13,913
￥15,652 total
Oct 4 - Oct 5
includes taxes & 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! (1,461 reviews)
"."

Reviewed on Sep 18, 2025

My Place Hotel-Medford OR
See all 673 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

Default Image

Historic Downtown District

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

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
Default Image

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

Siskiyou-Hargadine Historic District

Skidmore Academy Historic District, OR