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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 8,405 reviews and posted 4,867 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
We loved our stay at the Windsor Inn. The front desk staff was friendly and really willing to go out of their way to help. It's really a beautiful Tudor-style hotel with polished...
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Ashland Hills Hotel & Suites
#2 Hotel in Ashland
Ashland Hills Hotel & Suites
I wasn't expecting much, being a 3 star just off the 5 freeway. However it surpassed said expectations. The staff was super nice (shout out to Cori for making our late arrival so...
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Ashland Springs Hotel
#3 Hotel in Ashland
Ashland Springs Hotel
From check in to check out, every staff person we spoke to was extremely courteous and helpful. We had 2 small children and the hotel staff were very nice to our children also. We...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Aug
$464 round trip
Sep
$466 round trip
Oct
find price 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.