Ashland Vacations from $525

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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.
Sovana Inn

Sovana Inn

2 out of 5
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
8.2/10 Very Good! (1,004 reviews)
Staff at check-in was great. Morning staff was very congenial . Continental good but no yogurt Keurig coffee maker excellent.

Reviewed on May 22, 2024

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.2/10 Wonderful! (1,001 reviews)
The best part was the beach view.

Reviewed on May 24, 2024

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9/10 Wonderful! (1,539 reviews)
Great room with balcony and view. Poor continental breakfast

Reviewed on May 24, 2024

Lithia Springs Resort

Lithia Springs Resort

3 out of 5
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.4/10 Exceptional! (1,000 reviews)
Mineral water was amazing!

Reviewed on May 21, 2024

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.2/10 Wonderful! (531 reviews)
This was quite possibly the best hotel I have ever visited. The staff was amazing. The breakfasts were complex, interesting, and absolutely perfect in every way. The rooms included every amenity one could think of and several I could not have thought of. The hotel preserved a great deal of the history of the house, even things like a stereopticon with hundred-year-old pictures of the house. The staff was able to accommodate a celiac visitor who normally cannot eat out anywhere. I expect I will never stay anyplace else in Ashland again!

Reviewed on May 20, 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
Fully refundableReserve now, pay when you stay
The price is $115 per night from May 27 to May 28
$115
$128 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (1,518 reviews)
"The coffee maker reservoir did not look clean"

Reviewed on May 24, 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 $134 per night from May 27 to May 28
$134
$150 total
includes taxes & fees
May 27 - May 28
9/10 Wonderful! (1,526 reviews)
"Traveling with a dog is not easy. This hotel made it a lot easier"

Reviewed on May 22, 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 $114 per night from May 28 to May 29
$114
$116 total
includes taxes & fees
May 28 - May 29
8.6/10 Excellent! (1,001 reviews)
"Pool is very nice. Convenient to airport. Short drive to downtown, though not walkable."

Reviewed on May 18, 2024

Comfort Inn & Suites
See all 685 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 $525, 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.