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
Historic Downtown District
4 out of top 10 points of interest in this area
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.
Siskiyou-Hargadine Historic District
1 out of top 10 points of interest in this area
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 Oregon Cabaret Theatre and Allen Elizabethan 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 Oregon Shakespeare Festival 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
SAR 419
SAR 425 total
28 Sep - 29 Sep
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"The location is convenient, front desk customer service with a smile, shopping and restaurants nearby."
Reviewed on 31 August 2026
Best Western Windsor Inn
2520 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
SAR 422
SAR 471 total
7 Sep - 8 Sep
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"The room was very clean and the staff very helpful."
Reviewed on 30 August 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
SAR 389
SAR 471 total
2 Sep - 3 Sep
includes taxes & fees
8.8/10 Excellent! (1,536 reviews)
"We enjoyed this visit from the moment we arrived—from the friendly staff and inviting lobby to the beautiful outdoor pool and hot tub. The king-sized bed had a wealth of cloud soft pillows and the room was quiet. The staff put us on the ground floor with a direct exit outside for our pup. And downtown ..."
Reviewed on 30 August 2026
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.
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.
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.
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.
Ashland Library
8.4/10 (126 reviews)
The Ashland Library serves as a cultural hub with extensive collections and community programs. Browse local history materials or attend an author reading in this welcoming space connecting visitors to Ashland's literary scene.
Frequently asked questions
How much does an Ashland vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Ashland costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Ashland?
December, January and February are great times to search for cheap Ashland vacation packages. Traveling in quieter months means you'll typically find better prices on flights and hotels.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Ashland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Ashland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can tailor your Ashland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Ashland?
If you're considering an impromptu Ashland getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Ashland?
- Pick your travel dates: The things you'd like to do in Ashland and your favorite season can help you decide when to get away.
- Work out your budget: Make sure 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.
- Decide your trip length: Consider how much time you want to spend exploring Ashland. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Ashland vacation package for you.
