Ashland Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.

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.

Find hotels in Historic Downtown District
A tree-lined street with a mountain backdrop.

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.

Find hotels in Siskiyou-Hargadine Historic District
A rusted metal bridge in a forested area.

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.

Find hotels in Historic Railroad District
A town with buildings and trees in autumn colors, surrounded by mountains.

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 hotels in Skidmore Academy Historic District

Find the Best Ashland Vacation Packages

Ashland Hotel Deals

Best Western Windsor Inn

Best Western Windsor Inn

2520 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
NT$3,560
NT$3,970 total
Sep 27 - Sep 28
includes taxes & fees
Best Western Windsor Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
NT$3,545
NT$4,269 total
Sep 29 - Sep 30
includes taxes & fees
Ashland Hills Hotel & Suites
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

434 S. Valley View Rd. Ashland OR
Fully refundable
NT$3,361
NT$3,411 total
Sep 28 - Sep 29
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"We got our room and found it had a strong odor of cigarettes which this motel said was smoke free. I contacted the hotel receptionist and he gave us another room which turned out fine. One the exit doors would allow you to leave but you couldn’t use your room card to get back in. The breakfast was ..."

Reviewed on 2026/9/13

Comfort Inn & Suites Ashland
See all 775 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.

Stay near popular Ashland attractions

A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.
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.
See properties
A wood duck standing on rocks with moss and greenery in the background.

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.
See properties
A snowy forest with tall evergreen trees covered in snow.

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

Angus Bowmer Theatre

10.0/10 (11 reviews)
The heart of Oregon Shakespeare Festival, this intimate 600-seat venue places every audience member within 55 feet of the stage. Experience world-class performances where Shakespeare's words and contemporary works come alive.
See properties

Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.