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, Thomas Theatre and Oregon Shakespeare Festival are top sights worth seeing.

Find hotels in Historic Downtown District

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Ashland Hotel Deals

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$2,795 per night from Jan 1 to Jan 2
NT$2,795
NT$3,466 total
Jan 1 - 2026/1/2
includes taxes & fees
8.8/10 Excellent! (1,496 reviews)
Great

Reviewed on 2025/12/10

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundable
The price is NT$2,807 per night from Dec 15 to Dec 16
NT$2,807
NT$3,130 total
Dec 15 - Dec 16
includes taxes & fees
9.2/10 Wonderful! (1,597 reviews)
The room was clean and spacious. The best thing about our visit was chatting with Cindy over breakfast. She is a gem!!! She gave us quite a few suggestions for places to visit, and we really enjoyed chatting with her. She’s an excellent asset to your hotel and a keeper! We shall return!

Reviewed on 2025/12/10

Stratford Inn
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$2,106 per night from Dec 15 to Dec 16
NT$2,106
NT$2,348 total
Dec 15 - Dec 16
includes taxes & fees
8.6/10 Excellent! (1,190 reviews)
Huge room Great check in Very comfortable My 5th stay here

Reviewed on 2025/12/13

Flagship Inn of Ashland
See all 774 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 lively festivals and entertainment choices.

Southern Oregon University
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