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

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

Southern Oregon University

4.5/5(146 reviews)

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

Southern Oregon University

Lithia Park

4.5/5(481 reviews)

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

Lithia Park

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

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

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 SAR 882 per night from Jul 1 to Jul 2
SAR 882
SAR 983 total
1 Jul - 2 Jul
includes taxes & fees
Stay at this 3.5-star B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Oregon Shakespeare Festival and Allen Elizabethan ...
Quick last minute trip to Ashland to see plays
"We did a last minute trip to Ashland to see a few plays this past weekend. Susan and Adam the owners were wonderful hosts and very friendly. We left early in the AM of our check out date and was going to miss the scheduled 9am breakfast. Susan and Adam had a to go plate of the pastry being served ..."

Reviewed on 22 July 2024

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 SAR 405 per night from Jun 18 to Jun 19
SAR 405
SAR 456 total
18 Jun - 19 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! (2,009 reviews)
"Room was clean and bed was comfortable. Staff was friendly and helpful. The pool leaves a lot to be desired but if you don’t care about a pool then no worries! We were passing through on a road trip and for the price it was a nice place to stay. I’d stay again."

Reviewed on 13 June 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 SAR 475 per night from Jul 13 to Jul 14
SAR 475
SAR 568 total
13 Jul - 14 Jul
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! (1,415 reviews)
"Nice to rest"

Reviewed on 13 June 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 SAR 278 per night from Jun 30 to Jul 1
SAR 278
SAR 312 total
30 Jun - 1 Jul
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! (890 reviews)
"Amazing staff! Always a great visit!"

Reviewed on 13 June 2025

Ramada by Wyndham Medford Airport North
Compass by Margaritaville in Medford
Compass by Margaritaville in Medford
4 out of 5
2399 S Pacific Hwy, Medford, OR
Stay at this 4-star golf hotel in Medford. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
9.6/10 Exceptional! (887 reviews)
"Overall a great place to stay. My only complaint would be that you can hear everything in the hallway and noise from people in next room. However most hotels can be noisy."

Reviewed on 13 June 2025

Get rates
Compass by Margaritaville in Medford
Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
The price is SAR 350 per night from Jul 13 to Jul 14
SAR 350
SAR 355 total
13 Jul - 14 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,000 reviews)
"Very clean, well appointed, appears recently remodeled. Comfortable beds, big plus to have duvet covers. Quiet and highly functional AC If you want to be right near the freeway, great location and is quiet inside. Nice meadow view out the back. Close to downtown. However: due to an obstructing sign ..."

Reviewed on 11 June 2025

Comfort Inn & Suites Ashland
See all 657 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 Angus Bowmer Theatre 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

Skidmore Academy Historic District, OR

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