Cheap Flight Deals to Ashland OR from CA $127

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Ashland?

The cheapest prices found with in the last 7 days for return flights were CA $182 and CA $127 for one-way flights to Ashland for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
LAXMedfordJanuary 24 to January 25CA $182
SEAMedfordJanuary 16 to January 19CA $220
SFOMedfordJanuary 20 to January 27CA $264
OAKMedfordFebruary 24 to March 3CA $319
*Prices include taxes and fees

Your guide to flights to Ashland, OR

Alaska Airlines, Delta 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 $182 and CA $359. 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 $182. 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 $128 per night from Dec 21 to Dec 22
CA $128
CA $143 total
Dec 21 - Dec 22
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! (997 reviews)
We’ve stayed here twice. Nice place for reasonable price.

Reviewed on Nov 18, 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 $98 per night from Dec 9 to Dec 10
CA $98
CA $110 total
Dec 9 - Dec 10
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 ...
8.4/10 Very Good! (1,011 reviews)
Room very good and vintage 70s style.

Reviewed on Dec 4, 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 $121 per night from Dec 9 to Dec 10
CA $121
CA $134 total
Dec 9 - Dec 10
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
Save an average of 15% on thousands of hotels when you're signed in
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
The price is CA $87 per night from Dec 9 to Dec 10
CA $87
CA $98 total
Dec 9 - Dec 10
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! (1,176 reviews)
Clean and convenient. Staff was great

Reviewed on Dec 4, 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! (1,010 reviews)
The check-in was easy, the room was excellant, very clean with plenty of towels. The room had coffee, microwave and refrigerator ready to go along with a comfortable bed.

Reviewed on Dec 2, 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 $147 per night from Dec 10 to Dec 11
CA $147
CA $185 total
Dec 10 - Dec 11
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)
We had a great stay here. Very courteous staff, beautiful hotel, and a gated parking lot right behind the hotel. You can walk straight to the lot from the third floor. There's a lovely wrap-around balcony area overlooking the hotel lobby. Perfect place to relax and sip a beverage. Downtown Ashland ...

Reviewed on Dec 4, 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 $124 per night from Jan 1 to Jan 2
CA $124
CA $154 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,486 reviews)
Good stay. Sadly they don't offer a complimentary breakfast buffet anymore.

Reviewed on Dec 3, 2025

Opens in a new windowAshland Hills Hotel & Suites
Save an average of 15% on thousands of hotels when you're signed in
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
7100 Old Highway 99 South Ashland OR
The price is CA $142 per night from Dec 16 to Dec 17
CA $142
CA $165 total
Dec 16 - Dec 17
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! (1,170 reviews)
Great old lodge. Fun rooms with Jacuzzi tubs and fireplace. Restaurant was great and reasonably priced.

Reviewed on Dec 2, 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 $124 per night from Jan 1 to Jan 2
CA $124
CA $154 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,486 reviews)
Good stay. Sadly they don't offer a complimentary breakfast buffet anymore.

Reviewed on Dec 3, 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! (1,010 reviews)
The check-in was easy, the room was excellant, very clean with plenty of towels. The room had coffee, microwave and refrigerator ready to go along with a comfortable bed.

Reviewed on Dec 2, 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 $128 per night from Dec 21 to Dec 22
CA $128
CA $143 total
Dec 21 - Dec 22
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! (997 reviews)
We’ve stayed here twice. Nice place for reasonable price.

Reviewed on Nov 18, 2025

Opens in a new windowCedarwood Inn of Ashland
Save an average of 15% on thousands of hotels when you're signed in
Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
The price is CA $151 per night from Dec 14 to Dec 15
CA $151
CA $168 total
Dec 14 - Dec 15
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! (1,000 reviews)
clean room, friendly staff, good ex room, fresh coffee available

Reviewed on Dec 3, 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.