Ashland Vacations from $326

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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
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Seattle (SEA) 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

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.8/10 Exceptional! (9 reviews)
Lovely hosts, perfect location and beautiful surroundings, will always use Cowslip!!!

Reviewed on Sep 29, 2023

Hanna's House by WanderLodges

Hanna's House by WanderLodges

3 out of 5
Historic Railroad District
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
No reviews
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
8.8/10 Excellent! (1,148 reviews)
Wonderful experience in every aspect. Park and fly, with shuttle was so convenient

Reviewed on May 31, 2024

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
per person
Jul 18 - Jul 22
found 19 hours ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (575 reviews)
Relaxing, casual, fun

Reviewed on Jun 2, 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

5 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 $125 per night from Jun 10 to Jun 11
$125
$139 total
includes taxes & fees
Jun 10 - Jun 11
9/10 Wonderful! (1,522 reviews)
"The Stratford Inn provided a convenient stay for our visit to Ashland. The hotel is a convenient walk to Lithia Park and downtown with plenty of options for dining close by. My family enjoyed are stay and look forward to visiting again"

Reviewed on May 31, 2024

Stratford Inn
Ashland Hills Hotel & Suites
Ashland Hills Hotel & Suites
3 out of 5
2525 Ashland St, Ashland, OR
The price is $161 per night from Jun 4 to Jun 5
$161
$180 total
includes taxes & fees
Jun 4 - Jun 5
9/10 Wonderful! (1,537 reviews)
"It’s a bit tired but super nice people, clean, easy access, EV chargers"

Reviewed on Jun 1, 2024

Ashland Hills Hotel & Suites
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundableReserve now, pay when you stay
The price is $125 per night from Jun 23 to Jun 24
$125
$127 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (1,007 reviews)
Great Stay
"Had a great stay. It was clean and comfortable. Will be back in October."

Reviewed on May 28, 2024

Comfort Inn & Suites
See all 678 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 $326, 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 entertainment choices 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 acclaimed theater scene and entertainment choices.

Southern Oregon University

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