How much does an Ashland vacation package cost?

Offering excellent value package deals from $422 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?

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. 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. 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. 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. 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. 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.

Ashland Vacation Packages 2025/2026 from $422

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

$422

per person

Oct 12 - Oct 15

just found

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9.4/10 Exceptional! (1,003 reviews)

the ceilings were high in the rooms and the room was spacious

Reviewed on Aug 23, 2025

McCall House Boutique Inn

Historic Downtown District

$569

per person

Oct 12 - Oct 15

just found

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9.2/10 Wonderful! (569 reviews)

Very welcoming and hospitable staff. The breakfasts are delish, especially the fritata. Their attention to details are very strong.

Reviewed on Aug 15, 2025

A Cowslip's Belle Inn

$596

per person

Oct 12 - Oct 15

just found

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9.8/10 Exceptional! (35 reviews)

This was the perfect place to stay. Very charming and cute. Steve, the property manager, was awesome. Not only did he take the time to walk us through everything when we arrived but he also gave us restaurant recommendations where we could take our pups. Highly recommend.

Reviewed on Aug 22, 2025

Hummingbird Estate Wine & Suites

$511

per person

Oct 12 - Oct 15

just found

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9.6/10 Exceptional! (133 reviews)

It was great but a few in room amenities would be nice.

Reviewed on Jul 25, 2025

Ashland Springs Hotel

Historic Downtown District

$659

per person

Oct 12 - Oct 15

just found

Roundtrip non-stop flight included

Dallas (DFW) to Medford (MFR)

9.2/10 Wonderful! (1,002 reviews)

Historic property, perfectly located for Shakespeare Festival.

Reviewed on Aug 18, 2025

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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

Ashland Hotel Deals

Flagship Inn of Ashland

1193 Siskiyou Blvd, Ashland, OR

Fully refundableReserve now, pay when you stay

$69 nightly

$77 total

Sep 15 - Sep 16

Total with taxes and fees

8.8/10 Excellent! (1,002 reviews)

"Rooms are nice size and very clean. It's very quiet and fairly close to town. Beds are good, pillows also good. Staff was very friendly and helpful. We'd stay here again. The price was right."

Reviewed on Aug 22, 2025

Ashland Hills Hotel & Suites

2525 Ashland St, Ashland, OR

Fully refundableReserve now, pay when you stay

$143 nightly

$160 total

Sep 1 - Sep 2

Total with taxes and fees

8.8/10 Excellent! (1,449 reviews)

"Absolutely beautiful view"

Reviewed on Aug 20, 2025

Comfort Inn & Suites Ashland

434 S. Valley View Rd., Ashland, OR

Fully refundable

$105 nightly

$106 total

Sep 21 - Sep 22

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

"Great!"

Reviewed on Aug 20, 2025

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.

Things to do in and around Ashland

Ashland, Oregon, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of activities such as hiking, skiing, and exploring its scenic beauty. Visitors can enjoy wine tasting in the nearby vineyards and immerse themselves in the vibrant cultural experiences found in its renowned theater district. With a blend of recreation and relaxation, Ashland provides an unforgettable vacation destination filled with engaging activities and stunning landscapes.

Shopping

Ashland offers a vibrant shopping experience at the Lithia Artisans Market, showcasing local crafts and art. If you're up for a drive, the Rogue Valley Mall, 13 miles away, features a variety of shops and entertainment options, while the Rogue Creamery, 16 miles away, is perfect for gourmet cheese lovers.

Recreation

Experience the vibrant arts scene in Ashland by enjoying captivating performances at the Oregon Shakespeare Festival, Allen Elizabethan Theatre, or Oregon Cabaret Theatre. Each venue offers a blend of culture, romance, and family-friendly entertainment, making it a perfect retreat for relaxation and inspiration.

Adventure

Experience thrilling skiing at Mount Ashland Ski Area, where you can carve through fresh powder. Hike the Bull Gap Lower Trailhead for stunning outdoor scenery and adventure. Take a ride on the Ariel Ski Lift for breathtaking views and exhilarating moments high above the slopes.

Nightlife

Ashland's nightlife offers a vibrant mix of theaters and bars. Catch a performance at the Oregon Shakespeare Festival, then enjoy a craft beer at Caldera Brewing Company. For live music, check out the Historic Ashland Armory, where local talent shines in an inviting atmosphere.

*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 perfect for outdoor and scenic adventures, offering attractions like Ashland Creek and the Mount Ashland Ski Area. Visitors can explore urban parks and local universities while enjoying cultural experiences. Whether you're skiing at Mt. Ashland or discovering the charm of Ashland itself, there’s plenty to see and do for every type of traveler.

Southern Oregon University: Experience the vibrant atmosphere of this modern university located in the heart of Ashland. The campus features beautiful architecture and lively student life, making it a great place to explore galleries and attend cultural events.
Lithia Park: This urban park is a serene escape with stunning landscapes, playgrounds, and picnic areas. Ideal for families, it offers walking trails and a charming duck pond, providing a peaceful outdoor experience right in the city.
Howard Prairie Lake: A picturesque destination perfect for romance and outdoor activities. Enjoy swimming, fishing, or simply relaxing on the beach while taking in the breathtaking scenery of the surrounding mountains.

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.