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Your Ashland Vacation
Create your own exciting adventure with a tailor-made vacation package to Ashland. Its cultural experiences, progressive thinking and spectacular views are just the start of what you can expect in this interesting city. Ready to explore your surroundings? Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are just three of the best places to visit during a trip to Ashland. No matter your travel plans or the size of your budget, putting together a tailored Ashland vacation is simple with Expedia.
The Latest Ashland vacation packages


Hummingbird Estate Wine & Suites
Reviewed on Oct 18, 2025

Paschal Winery
Reviewed on May 3, 2025


Ashland Springs Hotel
Reviewed on Oct 9, 2025
Where to stay in Ashland

Historic Downtown District
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.
Discover the most popular places to visit in Ashland

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.

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.
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 acclaimed theater scene.
What to do in Ashland
Ashland Hotel Deals

Flagship Inn of Ashland
I really liked this hotel and would definitely stay again. Safe parking, great location, clean, good views and in summer the pool is great. The breakfast is disappointing but a least the coffee is good.
Reviewed on Oct 26, 2025

Ashland Hills Hotel & Suites
This hotel is an expansive, beautiful propert. I would recommend for any kind of traveler. The hottub was an extra bonus.
Reviewed on Oct 27, 2025

Stratford Inn
Staff was very helpful and cheerful. Older property, but well kept up. Very convenient location right in the middle of Ashland.
Reviewed on Oct 28, 2025
Find the Best Ashland Vacation Packages
Ashland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rogue Valley Intl. Airport (MFR) |
Population | 20,900 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre |
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- Hotels near Allen Elizabethan Theatre
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