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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 5,822 reviews and posted 2,787 candid photos for Ashland hotels. Book your Ashland vacation today!
Or build your own Ashland vacation package
Ashland Hills Hotel
#1 Hotel in Ashland
Ashland Hills Hotel
We lucked out and enjoyed a ground floor suite by the courtyard far from the road. Almost no one else at the hotel so it was soooo nice and quiet! However, when there were a few...
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Columbia Hotel
#2 Hotel in Ashland
Columbia Hotel
This hotel is a gem in downtown Ashland. The rooms are large and clean. The staff is very friendly. I would suggest getting a room with a bath, but even the shared baths were...
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BEST WESTERN Windsor Inn
#3 Hotel in Ashland
BEST WESTERN Windsor Inn
Rooms are charming and well appointed with spacious bathroom counter space with 2 sinks in the room we booked. High speed internet with a nice breakfast that included protein...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Dec
$998 round trip
Jan
find price round trip
Feb
$554 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.