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.

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
4.5/5(2 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Angus Bowmer Theatre are top sights worth seeing.

Find hotels in Historic Downtown District

Ready to book your vacation to Ashland?

 

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Ashland Hotel Deals

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 $190 per night from Jul 12 to Jul 13
CA $190
CA $227 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,514 reviews)
"Staff is very accommodating and friendly. Property is clean and nice. Bonus they accept dogs!"

Reviewed on Jul 7, 2026

Ashland Hills Hotel & Suites
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jul 12 to Jul 13
CA $154
CA $156 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"I got into town and discovered I was booked at the wrong property for my event. They refused to refund me any portion of the long stay. No exception. I hadn’t even stepped foot on the property yet and they charged me for the full stay."

Reviewed on Jul 7, 2026

Comfort Inn & Suites Ashland
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 8 to Jul 9
CA $135
CA $151 total
Jul 8 - Jul 9
includes taxes & fees
8.6/10 Excellent! (1,385 reviews)
"We booked and paid for a room online only to get to the hotel at 10 pm and have them tell us they didn't have a room for us. We had to call around and find another hotel, then spend another 90 minutes on the phone trying to get my money back.."

Reviewed on Jul 6, 2026

Prospero's Flagship Inn
See all 789 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.
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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
Open Photo by Patrick Glassford

Oregon Shakespeare Festival

9.2/10 (620 reviews)
You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
See properties

What to do in Ashland

An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

CA $14
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

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. Travelling in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Ashland?
Dedicate around 2 days for your Ashland vacation if you're hoping to discover all that makes this place special. Wander around key neighbourhoods, including Siskiyou-Hargadine Historic District and Historic Railroad District. Then check out top sights like Oregon Cabaret Theatre and Thomas Theatre. With a clever itinerary, you'll be kept busy with room for some me-time too. Want to venture beyond Ashland? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Ashland?
Well known for its cafes, cycling and hiking, an Ashland vacation is a hit with all types of travellers. Be sure to check out major sights like Oregon Shakespeare Festival and Lithia Park, and consider renting a set of wheels for day trips to discover even more.
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," "Traveller 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?

  1. Pick your travel dates: The things you'd like to do in Ashland and your favourite season can help you decide when to get away.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodations: Once you've nailed down your trip 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.