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.

Top Ashland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
Price was CA $514, price is now CA $514 per person
CA $514
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Medford (MFR)
9/10 Wonderful! (2,271 reviews)
The beds were comfortable, the room was nice and clean, check in was easy and staff was friendly.

Reviewed on Aug. 25, 2025

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
4.5/5(2 area reviews)

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

Ready to book your vacation to Ashland?

 

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Ashland Hotel Deals

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 CA $102 per night from Sep 10 to Sep 11
CA $102
CA $114 total
Sep 10 - Sep 11
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Reasonably priced stay - clean and comfortable; met the basics."

Reviewed on Aug. 25, 2025

Flagship Inn of 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 CA $167 per night from Sep 1 to Sep 2
CA $167
CA $200 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,454 reviews)
"I really like the unique amenities on this property. It is super kid friendly. Ot has a large pool, a playfround, tennis courts and plenty of places on property to sit and relax."

Reviewed on Aug. 24, 2025

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 refundable
The price is CA $153 per night from Sep 7 to Sep 8
CA $153
CA $155 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Bed was comfortable"

Reviewed on Aug. 22, 2025

Comfort Inn & Suites Ashland
See all 747 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Discover the most popular places to visit in Ashland

Thomas Theatre

You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's lively festivals and entertainment choices.

Thomas Theatre

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

CA $48
per traveller
Ashland Puzzling Adventure
Rafting Kikacéki

Kikacéki (Ward's) Canyon

CA $344
per adult
Kikacéki (Ward's) Canyon
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 from CA $514 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.

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