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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 6,637 reviews and posted 3,381 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
This is such a unique place. The luxuries are the fantastic food, outside dining patio, and the surroundings. I ate four meals outside on the patio and it's the kind of place...
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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
We found the hotel clean, both inside and out. The pool and hot tube were fun for the kiddos as well as the adults. It was just a couple of miles from downtown and Lithia Park...
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Plaza Inn & Suites at Ashland Creek
#3 Hotel in Ashland
Plaza Inn & Suites at Ashland Creek
We had a snafu with a VRBO and the owner put us up at this hotel. It did seem like they were having a little trouble accommodating a large changeover of room as our room was not...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Jul
$518 round trip
Aug
$564 round trip
Sep
$400 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.