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 Angus Bowmer Theatre.

Find hotels in Historic Downtown District

Top hotels in 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 S$206 per night from 12 Jul to 13 Jul
S$206
12 Jul - 13 Jul
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 7 Jul, 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 S$142 per night from 12 Jul to 13 Jul
S$142
12 Jul - 13 Jul
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 7 Jul, 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 S$129 per night from 8 Jul to 9 Jul
S$129
8 Jul - 9 Jul
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 6 Jul, 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.

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)
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.
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

S$13
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 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.