Ashland Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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
Historic Downtown District
5 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 Thomas Theatre.
Siskiyou-Hargadine Historic District
If you're spending some time in Siskiyou-Hargadine Historic District, Lithia Park and Ashland Library are top sights worth seeing.
Historic Railroad District
While Historic Railroad District isn't home to many top sights, Allen Elizabethan Theatre and Thomas Theatre are some notable places to visit nearby.
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 Thomas Theatre.
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
Comfort Inn & Suites Ashland
434 S. Valley View Rd. Ashland OR
Fully refundable
£85
10 Sept - 11 Sept
includes taxes & fees
8.8/10 Excellent! (1,028 reviews)
"The staff were just Wonderful! Jordan and Troy were so incredibly welcoming, friendly and helpful! Room was clean, peaceful and spacious. Bathroom was very clean."
Reviewed on 9 Aug 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
£114
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,525 reviews)
"convenient location"
Reviewed on 10 Aug 2026
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
£84
12 Aug - 13 Aug
includes taxes & fees
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
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.
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.
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.
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.
Thomas Theatre
9.4/10 (144 reviews)
This intimate theatre features flexible seating that brings audiences closer to contemporary works. Experience the emotional impact of minimalist staging that puts storytelling and actors at the heart of each production.
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.
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.
Angus Bowmer Theatre
10.0/10 (11 reviews)
The heart of Oregon Shakespeare Festival, this intimate 600-seat venue places every audience member within 55 feet of the stage. Experience world-class performances where Shakespeare's words and contemporary works come alive.
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
- 5 Star Hotels in White City
- Gay-Friendly Hotels in Ashland
- Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.
- Chateau Herb ~ Juliet Carriage House Studio
- Chateau Herbe ~ Athens Room
- Historic RUSHING WATER LODGE on the rogue river was built in 1910
- Gold Hill Hotels
- Cozy Cottage in Grants Pass Near River!
- Gay-Friendly Hotels in Grants Pass
- Stunning View
- Tropical Vibes in the Pines
- Grants Pass Hotels
- Jacksonville Hotels
- Comfort Inn & Suites Klamath Falls
- Harriman Springs Resort Cabin 3
- The Suites at The George 212
- Running Y Resort
- Klamath Falls Hotels
- Arden Forest Inn
- Ashland Springs Hotel
- Best Western Grants Pass Inn
- Best Western Horizon Inn
- Best Western Inn At The Rogue
- Callahan's Mountain Lodge
- Cedarwood Inn of Ashland
- Compass by Margaritaville in Medford
- Discovery Inn
- Downtown Mint
- Fairfield Inn & Suites by Marriott Medford
- Inn at the Commons
- Jacksonville's Historic Nunan House
- Lady Geneva Bed and Breakfast
- Large Private Carriage
- Mccall House Boutique Inn
- Red Lion Inn & Suites Grants Pass
- Resort at Eagle Point
- Riverside Inn
- The Lodge at Riverside
- Weasku Inn
- Winchester Inn
- Wine Suite at Rellik House. Winery & Alpaca Farm
- Merlin Hotels
- Union Creek Resort
- Prospect Hotels
- Cottages in Selma
- Family-Friendly Hotels in Southern Oregon
- Spa Hotels in White City
- White City Hotels
- Flights to Ashland
- Flights to Grants Pass
- Flights to Klamath Falls
- Flights to Medford
- Flights to Merlin
- Flights to Rogue River
- Flights to White City
- Flights from Rogue Valley Intl.
- Delta Seattle (SEA) to Medford (MFR) flights
- Flights from Keno
- Flights from Merlin
- Flights from Birmingham (BHX) to Medford (MFR)
- Flights from Bangkok (BKK) to Medford (MFR)
- Flights from Boston (BOS) to Medford (MFR)
- Flights from Denver (DEN) to Medford (MFR)
- Flights from Dublin (DUB) to Medford (MFR)
- Flights from Edinburgh (EDI) to Medford (MFR)
- Flights from East Midlands (EMA) to Medford (MFR)
- Flights from Glasgow (GLA) to Medford (MFR)
- Flights from New York (JFK) to Medford (MFR)
- Flights from Las Vegas (LAS) to Medford (MFR)
- Flights from Los Angeles (LAX) to Medford (MFR)
- Flights from Leeds (LBA) to Medford (MFR)
- Flights from London (LGW) to Medford (MFR)
- Flights from London (LHR) to Ashland (AHM)
- Flights from London (LHR) to Medford (MFR)
- Flights from Manchester (MAN) to Ashland (AHM)
- Flights from Manchester (MAN) to Medford (MFR)
- Flights from Manchester (MHT) to Medford (MFR)
- Flights from Newcastle (NCL) to Medford (MFR)
- Flights from Portland (PDX) to Medford (MFR)
- Flights from San Diego (SAN) to Medford (MFR)
- Flights from Seattle (SEA) to Medford (MFR)
- Flights from San Francisco (SFO) to Medford (MFR)
* 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.
