Skidmore Academy Historic District Travel Guide

Ashland

Photo by Shannon Willitts
Photo by Shannon Willitts

Popular places to visit

Oregon Shakespeare Festival

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
Mount Ashland Ski Area

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

Southern Oregon University

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's entertainment choices and acclaimed theatre scene.

Southern Oregon University

Lithia Park

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

Lithia Park

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

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

Top hotels in Skidmore Academy Historic District

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn

3.5 out of 5
451 North Main Street, Ashland, OR
The price is ฿8,470 per night from 28 Oct to 29 Oct
฿8,470
฿9,443 total
28 Oct - 29 Oct
includes taxes & fees
Stay at this 3.5-star B&B in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Allen Elizabethan Theatre and Angus Bowmer ...
9.6/10 Exceptional! (42 reviews)
Abigail's B & B
"Abigail's is a lovely B & B and the hosts are quite accommodating. We felt very welcome in their home and were provided several amenities including a blanket and seat cushions for the play we attended in the outdoor Elizabethan Theatre."

Reviewed on 14 Jul 2025

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 ฿3,518 per night from 19 Oct to 20 Oct
฿3,518
฿3,958 total
19 Oct - 20 Oct
includes taxes & fees
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! (2,503 reviews)
"The beds were very comfy, Loved that they had a nice dining menu on site, as well as complimentary breakfast. Nice quiet area too."

Reviewed on 12 Oct 2025

Rogue Regency Inn and Suites
My Place Hotel-Medford OR

My Place Hotel-Medford OR

3 out of 5
580 Airport Rd, Medford, OR
The price is ฿2,884 per night from 2 Nov to 3 Nov
฿2,884
฿3,245 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this 3-star 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 ...
9/10 Wonderful! (1,491 reviews)
"my entire day was outstanding"

Reviewed on 13 Oct 2025

My Place Hotel-Medford OR
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
The price is ฿3,656 per night from 23 Oct to 24 Oct
฿3,656
฿4,402 total
23 Oct - 24 Oct
includes taxes & fees
Stay at this 3-star ski hotel in Ashland. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,482 reviews)
"The hotel is nice and the quality is almost always the same, reliable, nice amenities. The beds are comfortable. Beautiful Ashland views. There are ebbs and flows with the staff…small town, some are great and fast some are good and slow. There are roaches by the hot tub beware, only saw them ..."

Reviewed on 13 Oct 2025

Ashland Hills Hotel & Suites
Quality Inn & Suites Medford Airport

Quality Inn & Suites Medford Airport

2.5 out of 5
1950 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
The price is ฿2,555 per night from 13 Nov to 14 Nov
฿2,555
฿2,889 total
13 Nov - 14 Nov
includes taxes & fees
Stay at this spa hotel in Medford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,013 reviews)
Nice place and convenient to the airport
"Shuttle was very accommodating and easy to find."

Reviewed on 10 Oct 2025

Quality Inn & Suites Medford Airport
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,079 reviews)
"great room, amazing staff! would stay here again!"

Reviewed on 9 Oct 2025

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Flagship Inn of Ashland
See all 669 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

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Historic Downtown District

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

Historic Downtown District
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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
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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