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.

Top Ashland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
per person
May 31 - Jun. 2
found 7 hours ago
Roundtrip flight included
Vancouver (YVR) to Medford (MFR)
9/10 Wonderful! (1,812 reviews)
The property is a little dated but it was clean and well maintained. Rooms were spacious and well appointed. Staff extremely friendly and helpful. Nothing fancy but perfect stop over on a road trip.

Reviewed on Apr. 18, 2025

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

3 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 hotels in Historic Downtown District

Ready to book your vacation to Ashland?

 

Choose your dates

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 $152 per night from Apr. 22 to Apr. 23
CA $152
CA $170 total
includes taxes & fees
Apr 22 - Apr 23
9.2/10 Wonderful! (1,541 reviews)
"Love this property! Staff is friendly and rooms are clean. Always stay here when I am in Ashland!"

Reviewed on Apr. 16, 2025

Stratford Inn
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 $174 per night from Apr. 28 to Apr. 29
CA $174
CA $201 total
includes taxes & fees
Apr 28 - Apr 29
9.2/10 Wonderful! (1,002 reviews)
"Just loved the building and the town in general. Very walkable"

Reviewed on Apr. 18, 2025

Ashland Springs Hotel
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 CA $161 per night from May 5 to May 6
CA $161
CA $193 total
includes taxes & fees
May 5 - May 6
8.8/10 Excellent! (1,444 reviews)
"Quiet and convenient. Friendly staff."

Reviewed on Apr. 17, 2025

Ashland Hills Hotel & Suites
See all 719 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

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Family Vacations

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Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals from CA $534 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 many days is enough for Ashland?
To fully enjoy an Ashland vacation, we suggest booking for 2 days. Divide your time between discovering Thomas Theatre, Schneider Museum of Art and other major sights, on top of exploring neighborhoods like Siskiyou-Hargadine Historic District and Historic Railroad District. If you’ve got some spare time, add a tour or day trip to your Ashland vacation itinerary.
Is it worth booking a vacation package to Ashland?
Whether you want to explore top sights like Oregon Shakespeare Festival and Lithia Park on your Ashland vacation, or coming for its great cafes, cycling and hiking, there’s something for everyone here. With so much to see and do, you’ll quickly learn why so many travelers think Ashland is a good vacation destination.
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

Thomas Theatre

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices.

Thomas Theatre

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

CA $50
per traveller
Ashland Puzzling Adventure
See all activities in Ashland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.