Ashland Vacations from $388

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Ashland Vacation

Discover Ashland's unique character and charm by booking an Ashland vacation package. Vacationers are drawn here by its progressive thinking, spectacular views and cultural experiences. Make your trip to Ashland even more fun and exciting by going sightseeing. Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are among the leading attractions worth exploring. Don't put off your visit to this destination any longer. The ultimate Ashland vacation is a couple of clicks away with Expedia.

The Latest Ashland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Relax Inn of Medford

Relax Inn of Medford

2.5 out of 5
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Medford (MFR)
6/10 (43 reviews)
We had an event close by so I booked it for convenience, hoping it would be as good as it was listed, I was not disappointed at all! Everything was clean and everyone was very friendly.

Reviewed on Sep 20, 2023

La Quinta Inn & Suites by Wyndham Central Point - Medford

La Quinta Inn & Suites by Wyndham Central Point - Medford

2.5 out of 5
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Medford (MFR)
6.8/10 (1,000 reviews)
The bed was lovely. The breakfast was good. The maintenance appears to be done by less than professionals. Place smelled like chlorine.

Reviewed on Jun 6, 2024

Super 8 by Wyndham Central Pt Medford

Super 8 by Wyndham Central Pt Medford

2 out of 5
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Medford (MFR)
6.6/10 (1,003 reviews)
The price was right for one night in the Medford area, however, I thought it was ridiculous that they would charge me $20 to check in early. It was a stupid inconvenience when of course there was a room ready.

Reviewed on Jun 3, 2024

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Medford (MFR)
9.4/10 Exceptional! (1,001 reviews)
Wonderful to see history so cherished. I truly enjoyed the 4 days there.

Reviewed on Jun 10, 2024

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Medford (MFR)
8.8/10 Excellent! (1,150 reviews)
Convenient to airport. Typical accommodations with amenities. Better than average free breakfast

Reviewed on Jun 10, 2024

Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Default Image

Historic Downtown District

4 out of top 10 points of interest in this area
5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Angus Bowmer Theatre are top sights worth seeing.

Find hotel + flight trips in Historic Downtown District

Ashland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Population
20,900
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre

Ashland Hotel Deals

Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
The price is $150 per night from Jun 16 to Jun 17
$150
$167 total
includes taxes & fees
Jun 16 - Jun 17
9/10 Wonderful! (1,526 reviews)
"At first I was a little concerned because the Inn is obviously old but it was really clean and comfortable. The showers were fab and instant hot water. The Continental breakfast was missing waffles but was well stocked otherwise and closely attended. We were an easy walk to the Shakespeare Festival ..."

Reviewed on Jun 8, 2024

Stratford Inn
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is $161 per night from Jun 18 to Jun 19
$161
$180 total
includes taxes & fees
Jun 18 - Jun 19
9/10 Wonderful! (1,549 reviews)
"Great stay"

Reviewed on Jun 8, 2024

Ashland Hills Hotel & Suites
Callahan's Mountain Lodge
Callahan's Mountain Lodge
3 out of 5
7100 Old Highway 99 South, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is $131 per night from Jun 18 to Jun 19
$131
$132 total
includes taxes & fees
Jun 18 - Jun 19
8.8/10 Excellent! (1,016 reviews)
"Beautiful lodge! Will definitely stay again if I’m in the area."

Reviewed on Jun 8, 2024

Callahan's Mountain Lodge
See all 675 properties in 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Ashland vacation package cost?
The most affordable Ashland package is $388, so your dream escape can become a reality — without it costing a fortune. Bundle flights, hotels, car rentals and more to customize a package suited to your traveling style.
How do I get a cheap travel package to Ashland?
You’ll save tons of cash if you bundle your hotels, car rentals and flights into an Ashland vacation package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels throughout the world, which means you’ll always have plenty of variety to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Ashland?
With fascinating attractions such as Oregon Shakespeare Festival and Southern Oregon University in this neighborhood, try to find a hotel near either of them. Mount Ashland Ski Area is another sight in Ashland that draws the crowds.
What are the top hotels in Ashland?
If you intend to stay in the Historic Railroad District neighborhood, some top options are Ashland Hills Hotel & Suites and Stratford Inn. Siskiyou-Hargadine Historic District is also a well-known Ashland area. We recommend Plaza Inn & Suites at Ashland Creek or Ashland Springs Hotel if you choose this part of the city.
How far in advance should I book my Ashland vacation?
It’s hard to pick the perfect time for airfares, but we generally suggest the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you’re booking late, don’t fret. Low prices occasionally appear within a few weeks of departure dates.
What does an Expedia Ashland travel package include?
That depends on you. You can select from a range of Ashland packages, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Ashland getaway looks like, you’ll save!
What should I know before booking an Ashland travel package?
You’ll land terrific savings when you bundle your flights, hotels and rental cars into a travel package. Not only that, booking everything in one spot makes trip planning easier. So why waste your time or money? Whether you’re organizing an upscale romantic escape or a low-cost family road trip, browse our vacation packages today.
Can I choose my airline with an Ashland Expedia vacation package?
Yes, and with more than 550 airlines to select from all over the world, you’ve got lots of choice. Search the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Ashland vacation package?
Whether it’s your flight or hotel, yes, you can cancel or amend it. Locked in your Ashland vacation package in the last 24 hours? You may be able to make changes for free. For bookings older than that, you may incur a fee from your hotel, airline or car rental company. For more information, take a look at our Customer Service Portal. We’re here to help you each step of the way.

Discover the most popular places to visit in Ashland

Image for Oregon Shakespeare Festival

Oregon Shakespeare Festival

4.5/5(265 reviews)

You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival
Image for Mount Ashland Ski Area

Mount Ashland Ski Area

4/5(70 reviews)

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and lively festivals in this walkable area.

Mount Ashland Ski Area
Image for Southern Oregon University

Southern Oregon University

4.5/5(146 reviews)

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's lively festivals and entertainment choices.

Southern Oregon University

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.