Ashland Holidays

Book a Hotel + Flight or Car together to unlock savings

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

4 out of top 10 points of interest in this area

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Angus Bowmer Theatre.

Find hotels in Historic Downtown District

Top hotels in Ashland

Comfort Inn & Suites Ashland
Comfort Inn & Suites Ashland
2.5 out of 5
434 S. Valley View Rd., Ashland, OR
Fully refundable
The price is 2.475.108 ₫ per night from 27 Jul to 28 Jul
2.475.108 ₫
2.512.234 ₫ total
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Fun and friendly staff . In process of remodel. Keep is nice while doing work . Loved the sheets and great towels. Comfortable beds ."

Reviewed on 28 Jun 2025

Comfort Inn & Suites Ashland
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 2.976.816 ₫ per night from 27 Jul to 28 Jul
2.976.816 ₫
3.580.380 ₫ total
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (1,427 reviews)
"I made this reservation 6-8mos ago, The front desk begrudgingly offered me a room with a view of the garden and was told to return at 4pm. When I returned I had to explain the change to the next front office person after she attempted to give me the parking lot view room. My feeling is, I was deprioritized ..."

Reviewed on 26 Jun 2025

Ashland Hills Hotel & Suites
Flagship Inn of Ashland
Flagship Inn of Ashland
2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is 2.663.934 ₫ per night from 6 Jul to 7 Jul
2.663.934 ₫
2.970.287 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Awesome overall helpful staff 2nd times at this hotel… first time I’m came up to early like 8am but check in time is 3 pm I’m ask for parking for waiting in my car with my daughter but Venessa ( staff) she say she will check for room available now for us and she get a bigger room for us at 8 am to ..."

Reviewed on 29 Jun 2025

Flagship Inn of Ashland
See all 740 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.

Frequently asked questions

How much does an Ashland holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Ashland costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Ashland?
If you're looking to score a cheap Ashland holiday package, consider visiting in December, January and February. You'll generally find better prices on accommodation and flights during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Ashland?
To fully enjoy an Ashland holiday, 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 neighbourhoods 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 holiday itinerary.
Is it worth booking a holiday package to Ashland?
Whether you want to explore top sights like Oregon Shakespeare Festival and Lithia Park on your Ashland holiday, 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 travellers think Ashland is a good holiday 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 personalise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?
You can enjoy significant savings on your Ashland break by booking a tailored holiday 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 holiday 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 favourite 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 accommodation: After you've settled on your dates and duration, lock in the right Ashland holiday package for you.

Popular places to visit

Mount Ashland Ski Area

Mount Ashland Ski Area

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

Southern Oregon University

Walk around the campus at Southern Oregon University during your visit to Ashland. Experience the area's entertainment choices and acclaimed theatre scene.

Southern Oregon University

Lithia Park

Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and lively festivals in this family-friendly area.

Lithia Park