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Ashland Vacation Packages

Oregon Shakespeare Festival
Evening in Ashland July 3rd.
A fall day in downtown Ashland
Ashland Vacation Packages
Want to book a vacation to Ashland? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Ashland vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Ashland on TripAdvisor by comparing Ashland hotel and flight prices. Travelers like you have written 6,413 reviews and posted 3,277 candid photos for Ashland hotels. Book your Ashland vacation today!
Or build your own Ashland vacation package
Plaza Inn & Suites at Ashland Creek
#1 Hotel in Ashland
Plaza Inn & Suites at Ashland Creek
The last time we stayed here for our trip to Ashland, it was a lot better than I expected. The lobby had a fireplace and was warm and comfortable. The rooms are big, nice, and...
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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
We were completely satisfied with our stay at the Best Western Windsor Inn. Either Best Western has upgraded as a chain or the Windsor Inn is a cut above the others. We were...
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Ashland Hills Hotel & Suites
#3 Hotel in Ashland
Ashland Hills Hotel & Suites
We were greeted by friendly staff who offered us cookies. This place is undergoing renovation. Our room was nice but I didn't like that we had no television in our bedroom...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Jun
$573 round trip
Jul
$658 round trip
Aug
$572 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.