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 get tickets for a performance 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

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's acclaimed theatre 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 savour the top-notch restaurants.

Howard Prairie Lake

Oregon Cabaret Theatre

You can get tickets for a performance at Oregon Cabaret Theatre during your stay in 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 RM529 per night from 22 Mar to 23 Mar
RM529
RM590 total
22 Mar - 23 Mar
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the pool in their reviews. Popular ...
9.4/10 Exceptional! (1,713 reviews)
Enjoyed my stay

Reviewed on 18 Mar 2026

Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is RM338 per night from 24 Mar to 25 Mar
RM338
RM400 total
24 Mar - 25 Mar
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
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 19 Mar 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 RM561 per night from 22 Mar to 23 Mar
RM561
RM678 total
22 Mar - 23 Mar
includes taxes & fees
Stay at this golf hotel in Medford. Enjoy free breakfast, free parking and a casino. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
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 19 Mar 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 RM375 per night from 31 Mar to 1 Apr
RM375
RM479 total
31 Mar - 1 Apr
includes taxes & fees
Stay at this spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,000 reviews)
Everything was excellent

Reviewed on 15 Mar 2026

Ashland Springs Hotel
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd Medford OR
The price is RM362 per night from 29 Mar to 30 Mar
RM362
RM407 total
29 Mar - 30 Mar
includes taxes & fees
Stay at this business-friendly hotel in Medford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,549 reviews)
For the price...My Place Hotel is perfect.

Reviewed on 18 Mar 2026

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

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

Reviewed on 16 Mar 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

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Thomas Theatre.

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

Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

Historic Railroad District
Street scene in downtown Ashland Oregon state.

Siskiyou-Hargadine Historic District

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

Siskiyou-Hargadine Historic District

Skidmore Academy Historic District