Skidmore Academy Historic District Vacations from $201

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Your Skidmore Academy Historic District Vacation

Planning your next adventure just got a whole lot simpler with a vacation package to Skidmore Academy Historic District. Take in the best this neighborhood has to offer while creating precious memories along the way. Want to sightsee during your trip to Skidmore Academy Historic District? Be sure to stop by nearby attractions like Southern Oregon University, Oregon Shakespeare Festival and Lithia Park. Whatever your travel plans or the size of your budget, booking your perfect Skidmore Academy Historic District vacation is quick and easy with Expedia.

The Latest Skidmore Academy Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Central Pt Medford

Super 8 by Wyndham Central Pt Medford

2 out of 5
Price was $280, price is now $201 per person
$201
per person
Nov 8 - Nov 11
found 15 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
7.2/10 Good! (1,012 reviews)
Kind Staff at the front desk. The pool is great! Decent rooms.

Reviewed on Sep 28, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $427, price is now $333 per person
$333
per person
Nov 8 - Nov 11
found 15 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (991 reviews)
Staff was very nice and very helpful. Property was very clean and nice.

Reviewed on Sep 29, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $483, price is now $378 per person
$378
per person
Nov 8 - Nov 11
found 15 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.2/10 Wonderful! (1,001 reviews)
The hotel was peaceful and the room I was in was very nice and clean. The view from my window was spectacular. Dining options around the area were nice. I was really happy for the parking garage offered to hotel guests as well. I came to watch a Shakespeare play and it was extremely walkable to the theater.

Reviewed on Sep 29, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $364, price is now $285 per person
$285
per person
Nov 8 - Nov 11
found 15 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9/10 Wonderful! (1,466 reviews)
Pet friendly. Thank you

Reviewed on Sep 29, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $692, price is now $546 per person
$546
per person
Dec 4 - Dec 7
found 14 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (571 reviews)
Very welcoming and hospitable staff. The breakfasts are delish, especially the fritata. Their attention to details are very strong.

Reviewed on Aug 15, 2025

Where to stay in Skidmore Academy Historic District

Find the best Skidmore Academy Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Skidmore Academy Historic District
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Historic Downtown District

4 out of top 10 points of interest in this area
5/5(133 area reviews)

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

Find hotels in Historic Downtown District

Skidmore Academy Historic District Hotel Deals

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn

3.5 out of 5
451 North Main Street, Ashland, OR
$260 nightly
The price is $290 total per night from Oct 6 to Oct 7
$290 total
Oct 6 - Oct 7
Total with taxes and fees
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 Jul 14, 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
$108 nightly
The price is $122 total per night from Oct 1 to Oct 2
$122 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (2,447 reviews)
"Close to places we needed to go."

Reviewed on Sep 26, 2025

Rogue Regency Inn and Suites
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $154 total per night from Oct 20 to Oct 21
$154 total
Oct 20 - Oct 21
Total with taxes and fees
8.8/10 Excellent! (1,479 reviews)
Definitely recommend
"Clean room, friendly staff and lots of parking. Location is great close to everything."

Reviewed on Sep 24, 2025

Ashland Hills Hotel & Suites
See all 674 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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Skidmore Academy Historic District

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
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and lively festivals in this walkable area.

Mount Ashland Ski Area

Southern Oregon University

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's entertainment choices and lively festivals.

Southern Oregon University

Things to do

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
See all activities in Ashland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.