Skidmore Academy Historic District

Ashland

Aerial view of Ashland, Oregon
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 acclaimed theatre scene 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

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

Thomas Theatre

You can get tickets for a performance at Thomas Theatre during your trip to Ashland. Experience the area's lively festivals and acclaimed theatre scene.

Thomas Theatre

Top hotels in Skidmore Academy Historic District

Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
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! (1,707 reviews)
we enjoyed the kitchenette

Reviewed on 5 Mar 2026

Get rates
Stratford Inn
Rogue Regency Inn Medford Airport

Rogue Regency Inn Medford Airport

3 out of 5
2300 Biddle Rd Medford OR
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! (2,863 reviews)
Wonderful place. Good People!

Reviewed on 5 Mar 2026

Get rates
Rogue Regency Inn Medford Airport
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is RM377 per night from 11 Mar to 12 Mar
RM377
RM480 total
11 Mar - 12 Mar
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! (1,006 reviews)
Will be returning. Fantastic historic hotel, holding on to its history.

Reviewed on 4 Mar 2026

Ashland Springs Hotel
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
2399 S Pacific Hwy Medford OR
The price is RM528 per night from 8 Mar to 9 Mar
RM528
RM642 total
8 Mar - 9 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! (1,009 reviews)
This was an exceptional property. The staff was amazingly helpful and friendly, the restaurant was great, and it was one of the best breakfast buffets I've seen yet. Great job!!!

Reviewed on 4 Mar 2026

Compass by Margaritaville in Medford
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is RM390 per night from 8 Mar to 9 Mar
RM390
RM475 total
8 Mar - 9 Mar
includes taxes & fees
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! (1,468 reviews)
I love staying here. We have a yearly gala at this location and I'm always excited to have an excuse for a night away from home.

Reviewed on 2 Mar 2026

Ashland Hills Hotel & Suites
Motel 6 Medford, OR - North

Motel 6 Medford, OR - North

2 out of 5
2400 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
The price is RM161 per night from 1 Apr to 2 Apr
RM161
RM181 total
1 Apr - 2 Apr
includes taxes & fees
Stay at this motel in Medford. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.4/10 Good! (1,115 reviews)
Was ok not bad

Reviewed on 2 Mar 2026

Motel 6 Medford, OR - North
See all 703 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 Thomas Theatre and Oregon Shakespeare Festival.

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 Thomas 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