Skidmore Academy Historic District Travel Guide

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

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

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

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd Medford OR
Stay at this business-friendly hotel in Medford. Enjoy free breakfast, free Wi-Fi and a free airport shuttle. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (2,833 reviews)
Clean and very helpful

Reviewed on 11 Feb 2026

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Rogue Regency Inn and Suites
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 ...
9.2/10 Wonderful! (1,683 reviews)
Close to downtown, great costumer service

Reviewed on 11 Feb 2026

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Stratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is Rp1.463.553 per night from 19 Feb to 20 Feb
Rp1.463.553
Rp1.884.285 total
19 Feb - 20 Feb
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! (1,001 reviews)
This place is beautiful!

Reviewed on 9 Feb 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 Rp2.257.708 per night from 18 Feb to 19 Feb
Rp2.257.708
Rp2.741.911 total
18 Feb - 19 Feb
includes taxes & fees
Stay at this golf hotel in Medford. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the pool in their reviews. ...
9.6/10 Exceptional! (1,009 reviews)
Room was spotless, friendly staff and very dog friendly

Reviewed on 11 Feb 2026

Compass by Margaritaville in Medford
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! (1,467 reviews)
Spotless clean. Great service. Amazing venue and dog friendly

Reviewed on 7 Feb 2026

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

Motel 6 Medford, OR - North

2 out of 5
2400 Biddle Rd Medford OR
The price is Rp643.809 per night from 18 Feb to 19 Feb
Rp643.809
Rp724.285 total
18 Feb - 19 Feb
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. ...
7.2/10 Good! (1,092 reviews)
Clean room, plenty of towels, heater worked well.

Reviewed on 13 Feb 2026

Motel 6 Medford, OR - North
See all 705 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 Travel Guide