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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 5,810 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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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
“Great!!” 11/21/2014
The Windsor Inn Ashland Oregon was awesome. Very nice accomodations. The bed was comfortable and room was very well appointed. Will stay here again and highly recommend. There was...
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Plaza Inn & Suites at Ashland Creek
#3 Hotel in Ashland
Plaza Inn & Suites at Ashland Creek
A great place to stay for the Shakespeare Festival” Reviewed 1 week ago NEW We have been staying a this hotel twice a year since they opened. We love the location near...
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Cheap Flights to Ashland
All New York to Medford (NYC-MFR) fares found by travelers in the past 72 hours*
Dec
$442 round trip
Jan
$484 round trip
Feb
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.