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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 8,644 reviews and posted 5,157 candid photos for Ashland hotels. Book your Ashland vacation today!
Or build your own Ashland vacation package
BEST WESTERN Windsor Inn
#1 Hotel in Ashland
BEST WESTERN Windsor Inn
My wife and I drove up to Ashland, OR and stayed her for one nite. We were impressed by the cleanliness of the hotel--even the TV remote was cleaned daily and the matress was...
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Ashland Hills Hotel & Suites
#2 Hotel in Ashland
Ashland Hills Hotel & Suites
Nicely updated, clean rooms, comfortable beds, nice atmosphere, delicious food at Luna Cafe located right in the hotel so it was also very convenient. Pool and hot tub were fun...
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BEST WESTERN Bard's Inn
#3 Hotel in Ashland
BEST WESTERN Bard's Inn
“Hidden Gem” 08/28/2016
This was a great Best Western with a great location in a hidden gem of a town. The hotel was walking distance to great restaurants, bars, movies and the theater. The service was...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Sep
$406 round trip
Oct
$406 round trip
Nov
$406 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.