We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

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 5,883 reviews and posted 2,795 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
Great place that's really trying hard to make it an awesome stay for those who come through. We stayed in a suite with a kitchenette for a week with a beautiful view of the...
1. Find your perfect hotel
2. Find the right flight
BEST WESTERN Windsor Inn
#2 Hotel in Ashland
BEST WESTERN Windsor Inn
This is a super nice place! Jessie at the front desk gave exemplary service. We really enjoyed our pet friendly stay in a ground floor room. The nearby Mexican Restaurant "El...
1. Find your perfect hotel
2. Find the right flight
Columbia Hotel
#3 Hotel in Ashland
Columbia Hotel
We stayed with our two children. I wanted a place downtown, so we could visit Lithia park in the morning. I don't like chain hotels and was happy to be able to stay in such a...
1. Find your perfect hotel
2. Find the right flight
Cheap Flights to Ashland
All Washington to Medford (WAS-MFR) fares found by travelers in the past 72 hours*
Jan
$430 round trip
Feb
$435 round trip
Mar
$543 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.