Ashland Vacations

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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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland

Discover the most popular places to visit in Ashland

Ashland Hotel Deals

Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Mar 8 to Mar 9
$123 total
Mar 8 - Mar 9
Total with taxes and fees
9.4/10 Exceptional! (1,707 reviews)
we enjoyed the kitchenette

Reviewed on Mar 5, 2026

Stratford Inn
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $134 total per night from Mar 8 to Mar 9
$134 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Will be returning. Fantastic historic hotel, holding on to its history.

Reviewed on Mar 4, 2026

Ashland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $113 total per night from Mar 15 to Mar 16
$113 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (1,468 reviews)
I love staying here. We have a yearly gala at this location and I'm always excited to have an excuse for a night away from home.

Reviewed on Mar 2, 2026

Ashland Hills Hotel & Suites
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.

Find the Best Ashland Vacation Packages

Things to do in and around Ashland

Ashland, Oregon, is perfect for outdoor enthusiasts and adventure seekers, offering a blend of scenic beauty and cultural experiences. Visitors can enjoy activities like exploring the renowned Oregon Shakespeare Festival, engaging in wine tasting tours, and partaking in recreational adventures across beautiful landscapes. With opportunities for skiing and a vibrant arts scene, Ashland promises an unforgettable getaway filled with diverse experiences.

Shopping

Ashland offers a delightful shopping experience with unique shops and local treasures. For a bit of a drive, Rogue Valley Mall, 13 miles away, features various stores and entertainment. Additionally, explore Kharmic Creations, 15 miles away, or visit Rogue Creamery, located 16 miles from the city for delicious artisanal cheeses.

Recreation

Experience the vibrant culture at the Oregon Shakespeare Festival, where captivating performances ignite the spirit. Enjoy the romantic ambiance of the Allen Elizabethan Theatre, offering enchanting shows. Unwind at the Oregon Cabaret Theatre, where delightful entertainment creates a warm, family-friendly atmosphere, perfect for relaxation and joy.

Adventure

Mount Ashland Ski Area offers exhilarating skiing experiences with stunning mountain views, perfect for both beginners and seasoned skiers. For an adventurous ride, the Comer Ski Lift provides easy access to thrilling slopes. Explore the Bull Gap Lower Trailhead for scenic hiking amidst breathtaking landscapes and outdoor adventures.

Nightlife

A night in Ashland offers a vibrant atmosphere, from live performances at the Oregon Shakespeare Festival to cozy drinks at local pubs like the Ashland Springs Hotel. For a lively evening, check out the nightly events at the Ashland Elks Lodge or enjoy a relaxed vibe at Caldera Tap House.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Ashland

Ashland, Oregon, is a fantastic destination for outdoor enthusiasts and adventure seekers, featuring beautiful lakes, urban parks, and modern colleges. Visitors can explore the scenic Ashland Creek, enjoy skiing at the Mount Ashland Ski Area, and discover the charming culture of the city. With its array of attractions and activities, Ashland promises a memorable experience that combines nature, adventure, and local culture.

  • Southern Oregon University: Experience the vibrant city atmosphere at Southern Oregon University, where modern architecture meets a lively campus life. Explore the beautiful grounds and engage with local students, enjoying the energy that this educational hub brings to Ashland.
  • Lithia Park: Enjoy a family-friendly outdoor escape at Lithia Park, a sprawling urban park filled with serene walking paths, picnic areas, and picturesque gardens. It’s a perfect spot for relaxation and recreation, right in the heart of the city.
  • Howard Prairie Lake: Discover the romantic charm of Howard Prairie Lake, a stunning natural oasis featuring sandy beaches and breathtaking scenery. Ideal for outdoor enthusiasts, it offers opportunities for swimming, fishing, and picnicking amidst serene landscapes.

Best time to go to Ashland

The best time to visit Ashland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly SunnyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June60.4°F (15.8°C)No RainMostly SunnySlightly HighSlightly High
July69.3°F (20.7°C)No RainSunnySlightly HighSlightly High
August68.7°F (20.4°C)No RainSunnyAverageSlightly High
September61.5°F (16.4°C)No RainSunnyAverageAverage
October51.1°F (10.6°C)Light RainMostly SunnySlightly LowAverage
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December34.7°F (1.5°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Ashland

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Ashland.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ashland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Population
20,900
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre

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Frequently asked questions

How much does an Ashland vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Ashland costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Ashland?
September, October and December are great times to search for cheap Ashland vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Ashland?
Dedicate at least 2 days for your Ashland vacation if you're hoping to take in everything that makes this place special. Explore key areas, including Siskiyou-Hargadine Historic District and Historic Railroad District. Then make a beeline for major sights like Oregon Cabaret Theatre and Thomas Theatre. With a well-organized itinerary, you'll be kept busy with room for some rest time too. Want to venture beyond Ashland? Consider an excursion or two.
Is it worth booking a vacation package to Ashland?
Popular for its cafes, cycling and hiking, an Ashland vacation is a hit with all kinds of travelers. Be sure to visit top sights like Oregon Shakespeare Festival and Lithia Park, and consider renting a car for day trips to experience even more.
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 personalize your search by "Amenities," "Property type," "Traveler 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 vacation as a package?
You can enjoy significant savings on your Ashland break by booking a tailored vacation 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 vacation 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 when to get away: Check your schedule and get your bags packed. Your preferred time of year and the available activities will also help you decide when to vacation in Ashland.
  2. Set your budget: Factor in costs such as flights, meals and transportation when working out how much to put aside for your trip to Ashland. Then, choose a hotel that fits your budget, whether that's an affordable stay or a more upscale getaway.
  3. Discover Ashland using our trip planning tool: Gain insights into the leading attractions and best stays for your trip to Ashland. You can also save your must-visit places, collaborate with your group and manage your plans in one place.
  4. Decide how long to go away for: Now that you know more about Ashland, you can figure out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Ashland vacation package.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some incredible things to do in Ashland in Ashland. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Ashland vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Ashland vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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