Ashland Vacation Packages

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Your Ashland Vacation

Create your own exciting adventure with a tailor-made vacation package to Ashland. Its cultural experiences, progressive thinking and spectacular views are just the start of what you can expect in this interesting city. Ready to explore your surroundings? Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are just three of the best places to visit during a trip to Ashland. No matter your travel plans or the size of your budget, putting together a tailored Ashland vacation is simple with Expedia.

Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
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Historic Downtown District

4 out of top 10 points of interest in this area
4.5/5(2 area reviews)

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

Find hotel + flight trips in Historic Downtown District

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 CA $117 per night from Apr. 22 to Apr. 23
CA $117
CA $131 total
includes taxes & fees
Apr 22 - Apr 23
9/10 Wonderful! (1,499 reviews)
"Nice, updated rooms and a friendly staff. Breakfast was good with a variety of breads, oatmeal and fruit. Conveniently located within walking distance to many dining options."

Reviewed on Apr. 15, 2024

Stratford Inn
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 CA $124 per night from Apr. 26 to Apr. 27
CA $124
CA $126 total
includes taxes & fees
Apr 26 - Apr 27
8.6/10 Excellent! (1,004 reviews)
"I loved that some items were 24/7. Love the location. Country view."

Reviewed on Apr. 15, 2024

Comfort Inn & Suites
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is CA $227 per night from Apr. 22 to Apr. 23
CA $227
CA $253 total
includes taxes & fees
Apr 22 - Apr 23
9.2/10 Wonderful! (1,004 reviews)
"I love the bedding and decor"

Reviewed on Apr. 12, 2024

Ashland Springs Hotel
See all 692 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.

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Frequently asked questions

How much does an Ashland vacation package cost?
The most affordable Ashland package is , 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

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

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

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

What to do in Ashland

Image for Ashland Puzzling Adventure

Ashland Puzzling Adventure

CA $47
Per adult
Ashland Puzzling Adventure
Image for Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

CA $57
Per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
See all activities in Ashland

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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.