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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 7,738 reviews and posted 4,155 candid photos for Ashland hotels. Book your Ashland vacation today!
Or build your own Ashland vacation package
Green Springs Inn
#1 Hotel in Ashland
Green Springs Inn
We arrived late in the day after a snowstorm which is an adventure in a Prius. The rustic entry to the lodge/restaurant provided the perfect stage for the warm hospitality from...
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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
Always a warm welcome and special treats for our little, old dog. There is plenty of lawn in the "doggie area" and pick up bags are provided, which is a nice touch. Above all...
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Plaza Inn & Suites at Ashland Creek
#3 Hotel in Ashland
Plaza Inn & Suites at Ashland Creek
My most recent stay was during a time when OSF was not in session -- so I got a very cheap rate through expedia. The hotel is in a great location -- a short walk to OSF and all...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Feb
$400 round trip
Mar
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Apr
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†  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.