Ashland Vacations from $272

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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 Latest Ashland vacation packages

Price found within the past 48 hours. Click for updated prices.
Wine Country Inn

Wine Country Inn

$272
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Medford (MFR)
9.4/10 Exceptional! (1,008 reviews)
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

Save 100% on your flight
$358
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Medford (MFR)
9.6/10 Exceptional! (185 reviews)
We stayed in the cottage because the main estate was booked. The main disappointment was that there was a coffee pot and filters but no coffee. Everything else was great! They had a dinner event the 1 night we stayed and the staff was very busy.

Reviewed on Aug 27, 2026

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

$365
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip flight included
Las Vegas (LAS) to Medford (MFR)
8.8/10 Excellent! (1,538 reviews)
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

$424
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Medford (MFR)
9.6/10 Exceptional! (1,083 reviews)
Lithia Springs Resort

Lithia Springs Resort

$290
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip flight included
Las Vegas (LAS) to Medford (MFR)
9.4/10 Exceptional! (1,006 reviews)
Bb

Reviewed on Sep 5, 2026

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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

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

1 out of top 10 points of interest in this area

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

A rusted metal bridge in a forested area.

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

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

Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

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 theater 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 wood duck standing on rocks with moss and greenery in the background.

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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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 savoring chef-prepared meals.
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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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Allen Elizabethan Theatre

9.4/10 (131 reviews)
This open-air Elizabethan-style theater 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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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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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.
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What to do in Ashland

Half-Day Rogue River Rafting with Indigo Creek

Rogue Valley Rapid Run

$110
per adult
100% of travellers recommend
Rogue Valley Rapid Run
An Audio Tour Through the Heart of Ashland, Oregon

The Cultural Heart of Ashland: A Self-Guided Audio Tour

$10
per adult
The Cultural Heart of Ashland: A Self-Guided Audio Tour
See all activities in Ashland

Ashland Hotel Deals

Best Western Windsor Inn

Best Western Windsor Inn

2520 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$113 nightly
$125 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Windsor Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$140 nightly
$156 total
Sep 13 - Sep 14
Total with taxes and fees
Ashland Hills Hotel & Suites
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

434 S. Valley View Rd. Ashland OR
Fully refundable
$106 nightly
$108 total
Sep 28 - Sep 29
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
"Good place to stay., everything we needed, definitely stay here again. Ashland has a lot of great restaurants and a active and fun downtown area. Much nicer than Medford with all the homelessness."

Reviewed on Sep 11, 2026

Comfort Inn & Suites Ashland
See all 775 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.

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 from $272 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.