Ashland Holidays

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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
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

While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

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A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

1 out of top 10 points of interest in this area

If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.

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A rusted metal bridge in a forested area.

Historic Railroad District

While Historic Railroad District isn't home to many top sights, Oregon Cabaret Theatre and Allen Elizabethan Theatre are some notable places to visit nearby.

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A town with buildings and trees in autumn colors, surrounded by mountains.

Skidmore Academy Historic District

While Skidmore Academy Historic District may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Allen Elizabethan Theatre and Oregon Shakespeare Festival.

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Top hotels in Ashland

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
€119
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,537 reviews)
"1) Very Disappointed that the property does Not have Secure Internet Access That makes it very dangerous to do any financial transactions while at the Property No Stock market trading No purchases that include providing financial and personal information I DON’T UNDERSTAND HOW THERE IS NO SECURE ..."

Reviewed on 31 Aug 2026

Ashland Hills Hotel & Suites
Prospero's Flagship Inn

Prospero's Flagship Inn

1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
€64
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,436 reviews)
"Be warned, check in is by a kiosk - there was no one actually in the lobby when I arrived at 8:00P. While the location is good, this particular motel will be bottom of the list for that reason. It's hard to have good customer service when there's no one there to assist. Breakfast was typical breakfast ..."

Reviewed on 31 Aug 2026

Prospero's Flagship Inn
Best Western Windsor Inn

Best Western Windsor Inn

2520 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
€108
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Everything was wonderful."

Reviewed on 1 Sept 2026

Best Western Windsor Inn
See all 769 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 theatre 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.
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A pond with ducks, surrounded by trees and a small bridge.
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.
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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.
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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.
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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 savouring chef-prepared meals.
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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.
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Allen Elizabethan Theatre

9.4/10 (131 reviews)
This open-air Elizabethan-style theatre hosts the renowned Oregon Shakespeare Festival. Evening performances unfold beneath the stars, creating a magical atmosphere reminiscent of Shakespeare's era.
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Ashland Library

8.4/10 (126 reviews)
The Ashland Library serves as a cultural hub with extensive collections and community programmes. Browse local history materials or attend an author reading in this welcoming space connecting visitors to Ashland's literary scene.
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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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.