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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 6,813 reviews and posted 3,459 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
We stayed at the green springs in while visiting family in ashland and had a great tine. The rooms are large and very clean, and the bed was extremely comfortable so we got great...
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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
We definitely will stay here again when visiting in the Ashland Area. The location was very convenient to I-5, yet close to the center of Ashland - 10 minute drive. At the Front...
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Ashland Springs Hotel
#3 Hotel in Ashland
Ashland Springs Hotel
We visited Ashland over July 4th weekend mainly for the Oregon Shakespeare theater, three nights - three plays, that were phenomenal. We arrived later than we expected and were...
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Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Aug
$400 round trip
Sep
$400 round trip
Oct
$474 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.