Ashland Vacations

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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
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 hotels in Historic Downtown District

Find the Best Ashland Vacation Packages

Ashland Hotel Deals

Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundable
The price is AED 349 per night from Jul 20 to Jul 21
AED 349
AED 354 total
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Fun and friendly staff . In process of remodel. Keep is nice while doing work . Loved the sheets and great towels. Comfortable beds ."

Reviewed on 28 June 2025

Comfort Inn & Suites Ashland
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 AED 419 per night from Jul 27 to Jul 28
AED 419
AED 503 total
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (1,428 reviews)
"I made this reservation 6-8mos ago, The front desk begrudgingly offered me a room with a view of the garden and was told to return at 4pm. When I returned I had to explain the change to the next front office person after she attempted to give me the parking lot view room. My feeling is, I was deprioritized ..."

Reviewed on 26 June 2025

Ashland Hills Hotel & Suites
Flagship Inn of Ashland
Flagship Inn of Ashland
2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AED 363 per night from Jul 6 to Jul 7
AED 363
AED 405 total
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Nice bed, shower could’ve been better. You can sell it and all establishment but relatively well establish kept"

Reviewed on 24 June 2025

Flagship Inn of Ashland
See all 740 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.

Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Ashland costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Ashland?
If you're looking to score a cheap Ashland vacation package, consider visiting in December, January and February. You'll generally find better prices on accommodations and flights during these quieter months --- perfect for a budget-friendly getaway.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Ashland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland vacation as a package?
You can enjoy significant savings on your Ashland break by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Ashland?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Ashland trip.
How to plan a trip to Ashland?

  1. Choose your travel dates: The things you plan to do in Ashland and your favorite season will help you decide when to get away.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Ashland.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Ashland. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, lock in the right Ashland vacation package for you.

Discover the most popular places to visit in Ashland

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

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
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

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

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 entertainment choices and acclaimed theater scene.

Southern Oregon University