Ashland Vacations from $307

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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

3 out of 5
Price was $381, price is now $307 per person
$307
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.4/10 Exceptional! (1,006 reviews)
Nice large room. Friendly and helpful front desk clerk.

Reviewed on Oct 20, 2025

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $895, price is now $709 per person
$709
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (138 reviews)
Absolutely lovely place to spend time, relax and enjoy the beautiful property and views. Highly recommend.

Reviewed on Oct 18, 2025

Paschal Winery

Paschal Winery

4.5 out of 5
Price was $656, price is now $535 per person
$535
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.6/10 Exceptional! (13 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

Green Springs Inn

Green Springs Inn

2 out of 5
Price was $427, price is now $354 per person
$354
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.4/10 Exceptional! (103 reviews)
It was all wonderful

Reviewed on Oct 27, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $546, price is now $454 per person
$454
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Medford (MFR)
9.2/10 Wonderful! (1,004 reviews)
It would be so charming to sit in the hotel lobby and have a cocktail by the beautiful fireplace except the fireplace hasn’t been used in years and there’s no bar

Reviewed on Oct 9, 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
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Historic Downtown District

4 out of top 10 points of interest in this area
5/5(133 area reviews)

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

Find hotels in Historic Downtown District

Discover the most popular places to visit in Ashland

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 reviews)

You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

4/5(70 reviews)

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and entertainment choices in this walkable area.

Mount Ashland Ski Area

Southern Oregon University

4.5/5(146 reviews)

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's entertainment choices and acclaimed theater scene.

Southern Oregon University

What to do in Ashland

Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
See all activities in Ashland

Ashland Hotel Deals

Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $64 total per night from Oct 30 to Oct 31
$64 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (1,107 reviews)
I really liked this hotel and would definitely stay again. Safe parking, great location, clean, good views and in summer the pool is great. The breakfast is disappointing but a least the coffee is good.

Reviewed on Oct 26, 2025

Flagship Inn of 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
$118 nightly
The price is $132 total per night from Nov 2 to Nov 3
$132 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,488 reviews)
This hotel is an expansive, beautiful propert. I would recommend for any kind of traveler. The hottub was an extra bonus.

Reviewed on Oct 27, 2025

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundable
$99 nightly
The price is $110 total per night from Nov 2 to Nov 3
$110 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,572 reviews)
Staff was very helpful and cheerful. Older property, but well kept up. Very convenient location right in the middle of Ashland.

Reviewed on Oct 28, 2025

Stratford Inn
See all 758 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

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 $307 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.

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.