Ashland Vacations from $330

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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.

The Latest Ashland vacation packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Central Point - Medford

La Quinta Inn & Suites by Wyndham Central Point - Medford

3 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
7.2/10 Good! (1,004 reviews)
To begin with, the sheets in one of our beds had a blood stain!!! There was a lot of construction going on in the place that was not communicated at booking. Staffing was minimal. I wouldn’t stay again

Reviewed on Jul 9, 2025

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.8/10 Exceptional! (33 reviews)
Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!

Reviewed on May 26, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.4/10 Exceptional! (1,002 reviews)
It’s an over 100 year hotel with old world charm. Stay knowing rooms and bathrooms will be smaller than modern hotels. But the charm and ease of getting around downtown made it well worth it.

Reviewed on Jul 4, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Medford (MFR)
9/10 Wonderful! (1,424 reviews)
Great stay! Our go to spot when in the area

Reviewed on Jul 8, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
9.6/10 Exceptional! (894 reviews)
The property is beautiful. Room was bright and fresh. Would definitely stay again!

Reviewed on Jul 8, 2025

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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

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 lively festivals and entertainment choices.

Southern Oregon University

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

$42
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
See all activities in Ashland

Ashland Hotel Deals

Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,014 reviews)
"Location is great. Nearby downtown. Representative is super friendly and he's very nice. Room is clean."

Reviewed on Jul 8, 2025

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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
8.8/10 Excellent! (1,429 reviews)
"Large rooms and great view from courtyard balcony."

Reviewed on Jul 5, 2025

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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
8.8/10 Excellent! (1,010 reviews)
"Aged property but still totally recommend. The rooms were big and spacious, having two sinks is really nice, the beds were comfy, towels plentiful staff excellent and helpful. Also, great location."

Reviewed on Jul 7, 2025

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Flagship Inn of Ashland
See all 725 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.

Find the Best Ashland Vacation Packages

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

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Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals from $330 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?
September, October and December are great times to search for cheap Ashland vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Ashland?
Dedicate at least 2 days for your Ashland vacation if you're hoping to take in everything that makes this place special. Explore key areas, including Siskiyou-Hargadine Historic District and Historic Railroad District. Then make a beeline for major sights like Oregon Cabaret Theatre and Thomas Theatre. With a well-organized itinerary, you'll be kept busy with room for some rest time too. Want to venture beyond Ashland? Consider an excursion or two.
Is it worth booking a vacation package to Ashland?
Popular for its cafes, cycling and hiking, an Ashland vacation is a hit with all kinds of travelers. Be sure to visit top sights like Oregon Shakespeare Festival and Lithia Park, and consider renting a car for day trips to experience even more.
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 when to get away: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to vacation in Ashland.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to put aside for your trip to Ashland. Then, choose a hotel that fits your budget, whether that's an affordable stay or a more upscale getaway.
  3. Discover Ashland using our trip planning tool: Gain insights into the leading attractions and best stays for your trip to Ashland. You can also save your must-visit places, collaborate with your group and manage your plans in one place.
  4. Decide how long to go away for: Now that you know more about Ashland, you can figure out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Ashland vacation package.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some incredible things to do in Ashland in Ashland. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Ashland vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Ashland vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.