Skidmore Academy Historic District Vacations from $359

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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.
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $469, price is now $359 per person
$359
per person
Oct 21 - Oct 24
found 21 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Medford (MFR)
9/10 Wonderful! (1,464 reviews)
Ashland Hotel and Suites is my preferred accommodation when I’m in Ashland. It’s a lovely property, and conveniently located close to I-5.

Reviewed on Sep 3, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Save 100% on your flight
Price was $1,153, price is now $769 per person
$769
per person
Oct 24 - Oct 29
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Medford (MFR)
9.2/10 Wonderful! (569 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

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $1,055, price is now $810 per person
$810
per person
Oct 24 - Oct 29
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Medford (MFR)
9.8/10 Exceptional! (36 reviews)
Lovely yard courtyard area with koi pond

Reviewed on Aug 25, 2025

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $625, price is now $485 per person
$485
per person
Nov 3 - Nov 7
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Medford (MFR)
9.4/10 Exceptional! (1,006 reviews)
Great experience, clean, nice staff

Reviewed on Sep 2, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $1,133, price is now $904 per person
$904
per person
Oct 24 - Oct 29
found 15 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Medford (MFR)
9.2/10 Wonderful! (1,004 reviews)
The hotel is interesting due its age. We checked in around 4:30 and got a mediocre room. The heating and air system was an issue because it would get warm then freezing throughout the night. Good location for the Shakespeare plays. Larks, the restaurant adjacent to the hotel was wonderful. The brussel sprout appetizer was amazing and the meat loaf was very tasty.

Reviewed on Sep 1, 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 Sep 4 to Sep 5
$290 total
Sep 4 - Sep 5
Total with taxes and fees
Abigail’s Bed & Breakfast Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $122 total per night from Sep 4 to Sep 5
$122 total
Sep 4 - Sep 5
Total with taxes and fees
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
$161 nightly
The price is $180 total per night from Sep 4 to Sep 5
$180 total
Sep 4 - Sep 5
Total with taxes and fees
Ashland Hills Hotel & Suites
See all 666 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
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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 entertainment choices 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 acclaimed theater scene 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.