Ashland Vacations from $360

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Your Ashland Vacation

When you choose a Ashland vacation package, you can kick back and enjoy your getaway to the fullest. Delve into the best things about this vibrant city knowing that everything has been organized in advance. Every trip to Ashland needs a well-thought-out itinerary. Fill yours with big-name attractions like Northern Great Lakes Visitor Center, Houghton Falls Nature Preserve and Bayfield County Courthouse. Expedia is here to help you escape the everyday. Tailor your vacation to Ashland to suit your travel style, whatever that may be.

The Latest Ashland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Suites Hotel at Waterfront Plaza
Barker's Island Inn Resort
Force on 5th Avenue Hotel
Pier B Resort
The Androy Hotel - Superior Duluth
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Ashland Hotel Deals

AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East, Ashland, WI
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $245 total per night from Aug 24 to Aug 25
$245 total
Aug 24 - Aug 25
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"Our bathroom ceiling had a slow water drip above the toilet. We called maintenance and they fixed it quickly."

Reviewed on Aug 15, 2025

AmericInn by Wyndham Ashland
Quality Inn Ashland - Lake Superior

Quality Inn Ashland - Lake Superior

2.5 out of 5
30600 Us Highway 2, Ashland, WI
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $181 total per night from Sep 7 to Sep 8
$181 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (856 reviews)
Room 106
"There was a leak in the bathroom and we told the front desk twice. Nobody came to inspect or fix it. The leak would drip on the toilet. It was a beautiful area and will be back - just not in room 106."

Reviewed on Aug 20, 2025

Quality Inn Ashland - Lake Superior
Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W., Ashland, WI
Fully refundableReserve now, pay when you stay
$226 nightly
The price is $254 total per night from Sep 21 to Sep 22
$254 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (685 reviews)
"Great location. Hotel very clean ."

Reviewed on Aug 21, 2025

Cobblestone Inn & Suites - 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.

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Frequently asked questions

How much does an Ashland vacation package cost?
You'll find cheap prices from $360 on Expedia for your Ashland break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Ashland costs.
What are the cheapest months to go to Ashland?
February, November and December are the best times to look for cheap Ashland vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Ashland?
You can easily visit all the main sights in Ashland within a few days, including the must-see Chequamegon Bay Golf Course. If you want a longer Ashland vacation, check out which kind of activities and day trips are available close by.
Is it worth booking a vacation package to Ashland?
Whether you want to visit major sights like Chequamegon Bay Golf Course and Ashland Historical Museum on your Ashland vacation, or coming for its great cycling, family-friendly attractions and walking trails, there's something for everyone here. With so much to experience, you'll soon find out why so many people think Ashland is a good vacation destination.
How to find the best Ashland package deals?
Use Expedia's handy filters to help you find some unbeatable Ashland package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Ashland package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Ashland vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize your Ashland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Ashland?
If you're considering a spontaneous Ashland trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Ashland vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Ashland vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.