Skidmore Academy Historic District

Ashland

Aerial view of Ashland, Oregon
Walked across the street from the ER and imagine this was the view from a physician parking lot

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
USA, Oregon, Mt Ashland. Fresh snow on evergreens.

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
A pretty male Wood Duck standing under the shade of a tree on the shoreline of a pond in a city park.

Lithia Park

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

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 entertainment choices.

Southern Oregon University

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

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

Top hotels in Skidmore Academy Historic District

Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is P8,114 per night from Mar 22 to Mar 23
P8,114
per night
Mar 22 - Mar 23
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,713 reviews)
Enjoyed my stay

Reviewed on Mar 18, 2026

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
The price is P5,193 per night from Mar 24 to Mar 25
P5,193
per night
Mar 24 - Mar 25
Book a stay at this business-friendly hotel in Medford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (2,884 reviews)
The staff is wonderful hotel and restaurant. The paint on the bathroom walls was pealing all bubled up

Reviewed on Mar 19, 2026

Rogue Regency Inn Medford Airport
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is P8,519 per night from Mar 31 to Apr 1
P8,519
per night
Mar 31 - Apr 1
Book a stay at this golf hotel in Medford. Enjoy free breakfast, free parking, and a casino. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.6/10 Exceptional! (1,000 reviews)
When your in your room and down in the lobby/ restaurant it's like your transformed to the somewhere tropical it's awesome. I was on a staycation would highly recommend it to anyone!!

Reviewed on Mar 19, 2026

Compass by Margaritaville in Medford
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is P5,752 per night from Mar 31 to Apr 1
P5,752
per night
Mar 31 - Apr 1
Book a stay at this 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! (1,000 reviews)
Everything was excellent

Reviewed on Mar 15, 2026

Ashland Springs Hotel
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is P5,550 per night from Mar 29 to Mar 30
P5,550
per night
Mar 29 - Mar 30
Book a stay at this business-friendly hotel in Medford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,549 reviews)
For the price...My Place Hotel is perfect.

Reviewed on Mar 18, 2026

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,444 reviews)
Great value, fun 70’s vibe, large rooms

Reviewed on Mar 16, 2026

Get rates
Ashland Hills Hotel & Suites
See all 704 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 neighbourhoods around Skidmore Academy Historic District

Landmark building in Ashland Oregon.

Historic Downtown District

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

Historic Downtown District
Mosby Creek Covered Bridge in Cottage Grove, Oregon, United States

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
Street scene in downtown Ashland Oregon state.

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