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Ashland Hotel + Air Packages

Oregon Shakespeare Festival
Evening in Ashland July 3rd.
A fall day in downtown Ashland
Build your own Ashland vacation package
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 5,192 reviews and posted 2,518 candid photos for Ashland hotels. Book your Ashland vacation today!
The Palm
#1 Hotel in Ashland
The Palm
I loved my stay at this old fashioned motel, with great upgrades. Enjoyed the nicely remodeled rooms (with A/C, free wi-fi), great beds, cabanas poolside, swimming in the pool at...
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BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
“Great Value” 07/29/2014
This hotel was a great value for the pool, fitness center, and breakfast. Not far from downtown Ashland and they have a free shuttle to downtown theaters and restaurants. The...
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Plaza Inn & Suites at Ashland Creek
#3 Hotel in Ashland
Plaza Inn & Suites at Ashland Creek
We loved our stay at the Plaza Inn! Loved it. A short walk (10 min maybe) to the Shakespeare Festival and Downtown shops and restaurants, clean rooms, plenty of safe parking at...
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2. Find the right flight
Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Aug
$479 round trip
Sep
$524 round trip
Oct
$408 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.