Cheap Flight Deals to Ashland OR from CA $158

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How to find cheap flights to Ashland?

The cheapest prices found with in the last 7 days for return flights were CA $139 and CA $158 for one-way flights to Ashland for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
SEAMedfordDecember 11 to December 14CA $139
DENMedfordJanuary 8 to January 14CA $310
PHXMedfordJanuary 10 to January 11CA $344
LAXMedfordDecember 6 to December 9CA $529
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
SLCMedfordNovember 23 to November 27CA $982
*Prices include taxes and fees

Your guide to flights to Ashland, OR

Alaska Airlines fly to Ashland, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Ashland OR currently costs between CA $139 and CA $982. Prices vary, but for the best fares, travel in January when prices are at their lowest.  

Top tips for finding cheap flights to Ashland  

The cheapest flight for a round trip to Ashland is currently CA $139. When you search for flights to Ashland, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Ashland for nearby days.  The cheapest month to travel to Ashland is January from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Ashland 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Ashland with Travelocity 

We have top deals on plane tickets even for last minute flights to Ashland, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Ashland for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Ashland

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

2 out of 5
Siskiyou Blvd, 1801 Ashland OR
The price is CA $122 per night from Nov 30 to Dec 1
CA $122
CA $137 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular ...
7.2/10 Good! (998 reviews)
Room was never serviced over 3 night stay. The renovations were nice and you can't beat the price for the area. I'd stay again.

Reviewed on Oct 15, 2025

Opens in a new windowCedarwood Inn of Ashland
Timbers INN and Suites

Timbers INN and Suites

2 out of 5
1450 Ashland Street Ashland OR
The price is CA $88 per night from Nov 21 to Nov 22
CA $88
CA $98 total
Nov 21 - Nov 22
includes taxes & fees
Stay at this motel in Ashland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.6/10 Excellent! (1,002 reviews)
Clean, well maintained, at a great price and location.

Reviewed on Nov 14, 2025

Opens in a new windowTimbers INN and Suites
Relax Inn At Ashland

Relax Inn At Ashland

1.5 out of 5
535 Clover Lane, Ashland, OR
The price is CA $120 per night from Nov 20 to Nov 21
CA $120
CA $134 total
Nov 20 - Nov 21
includes taxes & fees
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Weisinger Family Winery and ScienceWorks Hands-On Museum ...
6.8/10 (494 reviews)
The rooms are clean,everything worked, the price was right, very inexpensive.

Reviewed on Nov 3, 2025

Opens in a new windowRelax Inn At Ashland
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Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
The price is CA $58 per night from Nov 20 to Nov 21
CA $58
CA $65 total
Nov 20 - Nov 21
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,152 reviews)
-

Reviewed on Nov 15, 2025

Opens in a new windowFlagship Inn of Ashland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Ashland

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave Ashland OR
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
Desk staff was very nice room clean and quiet

Reviewed on Nov 14, 2025

Opens in a new windowPlaza Inn & Suites at Ashland Creek
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
The price is CA $149 per night from Nov 24 to Nov 25
CA $149
CA $187 total
Nov 24 - Nov 25
includes taxes & fees
Book a stay at this spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,002 reviews)
Beautiful ambiance. It’s like a hallmark movie

Reviewed on Nov 16, 2025

Opens in a new windowAshland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is CA $126 per night from Nov 23 to Nov 24
CA $126
CA $155 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,496 reviews)
Great room location to courtyard to take family pup out side. Quiet. Comfy bed

Reviewed on Nov 10, 2025

Opens in a new windowAshland Hills Hotel & Suites
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Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
7100 Old Highway 99 South Ashland OR
The price is CA $138 per night from Dec 10 to Dec 11
CA $138
CA $162 total
Dec 10 - Dec 11
includes taxes & fees
Book a stay at this family-friendly lodge in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in ...
8.6/10 Excellent! (1,169 reviews)
All was perfect! 5 stars

Reviewed on Nov 14, 2025

Opens in a new windowCallahan's Mountain Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Ashland

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
The price is CA $126 per night from Nov 23 to Nov 24
CA $126
CA $155 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,496 reviews)
Great room location to courtyard to take family pup out side. Quiet. Comfy bed

Reviewed on Nov 10, 2025

Opens in a new windowAshland Hills Hotel & Suites
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave Ashland OR
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
Desk staff was very nice room clean and quiet

Reviewed on Nov 14, 2025

Opens in a new windowPlaza Inn & Suites at Ashland Creek
Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

2 out of 5
Siskiyou Blvd, 1801 Ashland OR
The price is CA $122 per night from Nov 30 to Dec 1
CA $122
CA $137 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular ...
7.2/10 Good! (998 reviews)
Room was never serviced over 3 night stay. The renovations were nice and you can't beat the price for the area. I'd stay again.

Reviewed on Oct 15, 2025

Opens in a new windowCedarwood Inn of Ashland
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Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
The price is CA $152 per night from Nov 28 to Nov 29
CA $152
CA $170 total
Nov 28 - Nov 29
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,001 reviews)
Ryan, front desk, was very considerate. The room was clean and quiet. Bed was firm.

Reviewed on Nov 8, 2025

Opens in a new windowBest Western Windsor Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a car after flight to Ashland?

Flights To Ashland

For a vacation filled with the sights and sounds of the largest regional repertory theater in the United States, check out flights to Ashland, Oregon. From February to October, the heart of the city throbs with the Oregon Shakespeare Festival, making it a destination for theater and music lovers. Ashland vacation packages are a frugal choice when booking travel to arts events in the area. The nearby Medford International Airport (MFR) takes you to the heart of the Rogue Valley; only a few miles north of Ashland.

Transportation from MFR

Hotels near Medford International Airport are a convenient base to explore the rich Rogue Valley and its attractions. While bus transportation is available, a rental car is the easiest way to get around the valley as you travel the 16.2 miles south on I-5 to Ashland or head north to the nearby cities of Rogue River or Grants Pass. In addition to the world-renowned Shakespeare Festival, Ashland is the home of Southern Oregon University and the National Fish and Wildlife Forensics Laboratory, where experts help solve crimes against wildlife. Summer rafting on the Rogue River and winter skiing at Mt. Ashland make Ashland and the Rogue Valley a year-round destination. Ashland hotels are only a few miles down the mountain from the skiing and snowboarding in winter, but be prepared with chains for snowy roads.

Visit Ashland

In addition to the Oregon Shakespeare Festival, Ashland hosts a wide variety of musical and theatrical venues. Immerse yourself in the public concerts, comedy shows, and festivals held in and around the Ashland area and don't forget to take home some of the fruits from the orchards that fill the valley. When booking Ashland flights, save up to $537 when you book a hotel and flight at the same time. Travelocity will help you find the best deals on Ashland airfare, allowing you to save money to take in one more performance before heading home.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.