Ashland Vacations from $361

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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

2.5 out of 5
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
6.8/10 (1,000 reviews)
Good hotel for a quick night stay

Reviewed on Sep 24, 2024

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.8/10 Exceptional! (22 reviews)
Great spot. Quiet, nice surroundings. Pleasant rental keeper.

Reviewed on Sep 25, 2024

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.4/10 Exceptional! (1,000 reviews)
Rooms are smaller than modern hotels but it was clean and had all we needed. Great experience with staff, location was ideal for plays.

Reviewed on Sep 23, 2024

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges

4 out of 5
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
10/10 Exceptional! (1 review)
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9/10 Wonderful! (1,509 reviews)
We only stay at Ashland Hills when in Ashland. Rooms are nice. A few minor upgrades in the rooms would add an extra star. Too bad The Luna Cafe changed their menu. Use to be fantastic.

Reviewed on Sep 23, 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

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 Oregon Shakespeare Festival 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

Ready to book your vacation to Ashland?

 

Choose your dates

Ashland Hotel Deals

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 $159 per night from Oct 1 to Oct 2
$159
includes taxes & fees
$143 per night
Oct 1 - Oct 2
9/10 Wonderful! (1,512 reviews)
"This is an older property that has been completely renovated but still has a groovy late mid-century vibe. Cool artwork, very comfy beds. Questionable design decision to leave the circa-1970 hanging light fixture in the room, truly hideous thing. Large piece of adjacent vacant land was handy for ..."

Reviewed on Sep 23, 2024

Ashland Hills Hotel & Suites
Stratford Inn
Stratford Inn
2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is $117 per night from Sep 29 to Sep 30
$117
includes taxes & fees
$105 per night
Sep 29 - Sep 30
9/10 Wonderful! (1,407 reviews)
"Receptionist was excellent on a busy check in night."

Reviewed on Sep 24, 2024

Stratford Inn
Callahan's Mountain Lodge
Callahan's Mountain Lodge
3 out of 5
7100 Old Highway 99 South, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is $125 per night from Sep 29 to Sep 30
$125
includes taxes & fees
$123 per night
Sep 29 - Sep 30
8.6/10 Excellent! (1,014 reviews)
"The rooms smelled like stale smoke, and the rugs were dirty. The beds were comfortable and the sheets were clean. The service was great and the food was pretty good."

Reviewed on Sep 23, 2024

Callahan's Mountain Lodge
See all 708 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?
Offering excellent value package deals from $361 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?
Ashland has everything you need for a fantastic break — cafes, cycling and hiking are just the start. Whether you want to visit sights like Oregon Shakespeare Festival and Lithia Park, or venture off the beaten track, you’ll have plenty to do on your Ashland vacation.
How to find the best Ashland package deals?
Use Expedia’s filter tool to help you find some great Ashland package deals. When you begin your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or look for Ashland package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to book your vacation package well in advance.
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?
If you’ve got your Ashland vacation dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Ashland?

  1. Pick your travel dates: What you’d like to do in Ashland and your preferred season will help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Ashland.
  3. Organize your Ashland escape with Expedia’s trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Ashland together.
  4. Decide how many days away: Start by listing all the activities and attractions you’d like to experience in Ashland. Then, estimate how long you’ll need for each, including any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Ashland vacation package.
  6. Add on experiences and excursions: Have a look at our travel guide to find some exciting things to do in Ashland. Book tickets or make reservations in advance to save time and skip the hassle of trying to find 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.

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 lively festivals and entertainment choices.

Southern Oregon University

What to do in Ashland

Image for Ashland Puzzling Adventure

Ashland Puzzling Adventure

$35
Per adult
Ashland Puzzling Adventure
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.