Ashland Vacations from ￥368,055
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The Latest Ashland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites – Yreka, Ca
￥373,210
per person
Oct 4 - Oct 10
just found
Roundtrip flight included
Fukuoka (FUK) to Medford (MFR)
10/10 Exceptional! (1 review)
We stayed at Studio 6 Suites for one night during our road trip to Mount Shasta and were pleasantly surprised. Our room was recently renovated, very clean and fresh, with no unpleasant odors. The furniture looked new, the bed was very comfortable, and the bathroom was spacious, bright, and clean.
The guy at the front desk was very attentive and helpful. He listened to our requests and made sure we got exactly what we wanted.
Overall, we really enjoyed our stay and were very satisfied. Clean, comfortable, and a great place to stay during a road trip.
Reviewed on Aug 11, 2026
Where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Historic Downtown District
5 out of top 10 points of interest in this area
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Thomas Theatre are top sights worth seeing.
Siskiyou-Hargadine Historic District
While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.
Historic Railroad District
Historic Railroad District might not have many top sights, but Allen Elizabethan Theatre and Thomas Theatre are two attractions nearby that you can check out.
Skidmore Academy Historic District
Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Thomas Theatre are two attractions nearby that you can check out.
Find the Best Ashland Vacation Packages
Ashland Hotel Deals
Comfort Inn & Suites Ashland
434 S. Valley View Rd. Ashland OR
Fully refundable
￥18,174
￥18,447 total
Aug 27 - Aug 28
includes taxes & fees
8.8/10 Excellent! (1,030 reviews)
"Very clean, updated decor, comfy beds, great breakfast, helpful staff."
Reviewed on Aug 10, 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
￥18,777
￥22,529 total
Sep 7 - Sep 8
includes taxes & fees
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
￥14,685
￥16,373 total
Aug 17 - Aug 18
includes taxes & fees
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.
Stay near popular Ashland attractions
Photo by Patrick Glassford
Oregon Shakespeare Festival
9.2/10 (620 reviews)
At OSF, America's oldest repertory theater presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.
Photo by Shannon Willitts
Lithia Park
9.6/10 (1,250 reviews)
Stroll through Lithia Park's 93 acres of landscaped beauty alongside Ashland Creek. Discover Japanese gardens, duck ponds, and seasonal foliage while enjoying the serenity of this historic green space.
Mount Ashland Ski Area
8.6/10 (228 reviews)
Southern Oregon's premier ski destination offers 44 trails across 240 acres of varied terrain. Enjoy twilight skiing on select evenings for a magical mountain experience under the stars.
Howard Prairie Lake
8.4/10 (33 reviews)
A pristine 1,990-acre reservoir in the Cascade Mountains, Howard Prairie Lake offers exceptional trout and bass fishing. Enjoy tranquil boating amid pine forests or unwind at the lakeside resort with mountain views.
Thomas Theatre
9.4/10 (144 reviews)
This intimate theater features flexible seating that brings audiences closer to contemporary works. Experience the emotional impact of minimalist staging that puts storytelling and actors at the heart of each production.
Allen Elizabethan Theatre
9.4/10 (131 reviews)
This open-air Elizabethan-style theater hosts the renowned Oregon Shakespeare Festival. Evening performances unfold beneath the stars, creating a magical atmosphere reminiscent of Shakespeare's era.
Emigrant Lake
8.4/10 (70 reviews)
Emigrant Lake offers warm waters and scenic views just five miles from Ashland, Oregon. Enjoy the thrilling 280-foot twin flume water slide during summer or camp beneath the stars in this recreational haven.
Oregon Cabaret Theatre
9.0/10 (144 reviews)
Set in a restored 1911 mission-style church, Oregon Cabaret Theatre pairs professional musical performances with gourmet dining. Enjoy tiered seating with balcony views while savoring chef-prepared meals.
What to do in Ashland
The Cultural Heart of Ashland: A Self-Guided Audio Tour
￥1,595
per adult
Frequently asked questions
How much does an Ashland vacation package cost?
Offering excellent value package deals from ￥368,055 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?
- Choose your travel dates: The things you plan to do in Ashland and your favorite season will help you decide when to get away.
- 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.
- 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.
- Combine your airfare and accommodations: After you've settled on your dates and duration, lock in the right Ashland vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
