Ashland Vacations

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Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
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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

Find the Best Ashland Vacation Packages

Ashland Hotel Deals

Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NT$1,940 per night from Oct 26 to Oct 27
NT$1,940
NT$2,163 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (1,109 reviews)
Great room and great service. I'd asked for a scent-neutral room and the Flagship staff came through wonderfully. Comfortable, convenient, everything I needed. I'll be back for sure!

Reviewed on 2025/10/21

Flagship Inn of Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is NT$3,456 per night from Nov 2 to Nov 3
NT$3,456
NT$4,161 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (1,482 reviews)
Nice simple hotel. Comfortable and convenient location. Nothing fancy, but perfectly adequate.

Reviewed on 2025/10/24

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundable
The price is NT$3,325 per night from Nov 3 to Nov 4
NT$3,325
NT$3,708 total
Nov 3 - Nov 4
includes taxes & fees
9.2/10 Wonderful! (1,568 reviews)
We had a very nice stay! Rooms were comfortable, and the location is great - many great dining choices and entertainment within walking distance of the hotel.

Reviewed on 2025/10/23

Stratford Inn
See all 751 properties in Ashland
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.

Discover the most popular places to visit in Ashland

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

4.5/5(265 reviews)

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

4/5(70 reviews)

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

4.5/5(146 reviews)

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

Southern Oregon University
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