Ashland Holidays

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Your Ashland Holiday

Create your own exciting adventure with a tailor-made holiday 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 holiday 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

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

Find hotels in Historic Downtown District

Ashland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Population
20,900
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre

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 £119 per night from 20 Jul to 21 Jul
£119
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,521 reviews)
"Cleaning room; staff was very helpful to reserve a quite room in advance."

Reviewed on 11 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 refundable
The price is £83 per night from 9 Aug to 10 Aug
£83
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
"Safe place to stay but it could use some upgrades"

Reviewed on 12 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 £67 per night from 20 Jul to 21 Jul
£67
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (1,396 reviews)
"I don’t mind that they only cleaned the room once during the week I stayed, but they need to supply enough toilet paper, coffee pods, coffee cups, etc to last more than one day."

Reviewed on 11 Jul 2026

Prospero's Flagship Inn
See all 792 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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

Frequently asked questions

Why should I book my Ashland holiday with Expedia?
With top-value airfares, car hire and hotel options all in the same place, Expedia makes planning your Ashland adventure easy. What's more, we can help you bundle your bookings into a package holiday so you can save even more. Select from fabulous properties, add flights and/or a car hire (and maybe also some fun activities!) and land incredible prices. Need to cancel? Expedia has a flexible cancellation policy for many bookings. To discover more, check out our Customer Service Portal link.
When is the best time of year to holiday in Ashland?
If you want to experience the buzz of Ashland during the high season, organise your getaway for March, April and November. September, October and December are typically the quietest months of the year. Organise your escape to Ashland according to what kind of adventure you're looking for. December is the coolest time of year, when average daytime temperatures are 1ºC. In July, the warmest period, you will experience averages of 20ºC during the day.
What are the top hotels for my holiday in Ashland?
Comfort Inn & Suites and Ashland Hills Hotel & Suites are among the best escapes in the Historic Railroad District neighbourhood. If you prefer to spend time in the Siskiyou-Hargadine Historic District area, book a few nights at Plaza Inn & Suites at Ashland Creek or Best Western Windsor Inn.
How do I get a cheap holiday to Ashland?
Secure flights that suit your schedule, add a hotel room to your booking and watch the savings grow with an Ashland holiday. It's as simple as that! From hotels and flights to tours and hire cars, Expedia makes travelling cheaply a cinch. And with more than 400 partner airlines and 321,000 properties globally to pick from, you won't be short of choice. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Ashland holiday?
Offering major attractions such as Oregon Shakespeare Festival and Southern Oregon University, a holiday in Ashland is packed with fun things to see and do. Mount Ashland Ski Area and Lithia Park are two other sights worth checking out.
What is the best area to stay in when on holiday in Ashland?
Ashland has many wonderful places to explore, like Oregon Shakespeare Festival. Stay someplace near this attraction and make sightseeing hassle-free.
Do I need a visa for my Ashland holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the reason for your visit, whether it be for holidays or business, will determine if you need a visa for Ashland. Also ensure your passport is up to date and has at least six months validity remaining beyond your date of return. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Ashland holiday?
First, consider the sorts of activities you have planned during your holiday in Ashland and select versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, browse style blogs or social media accounts. Daytime temperatures during December, Ashland's coolest month, average 1ºC. July marks this city's warmest month when average temperatures reach 20ºC. Our top tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Ashland holiday include?
Flights, hotels and car hires, or any combination of them — it's totally up to you. Whether you're visiting Ashland with the entire family or enjoying a solo break, there's a package to suit your style and budget. Once you've made your booking, why not add on one or two tours and experiences? Discover a huge range of property types and pick one that fits the size of your group. The most in-demand holiday rentals here are private holiday homes and cottages. With Expedia, it's easy to design your Ashland escape the way you like.
Does Expedia offer Book Now, Pay Later Ashland holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply pick the payment plan that works for you during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy payment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • No-deposit holidays: Clicking the "book now" button is easier with this payment option. With no deposit required for your holiday, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with an Ashland Expedia holiday?
Yes, you're in charge. Expedia has access to more than 400 partner airlines around the world, so you can design your Ashland adventure according to your needs and budget.

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. Flight-inclusive packages are ATOL protected.