Ashland Vacations from $728

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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 Androy Hotel - Superior Duluth
Pier B Resort
The Suites Hotel at Waterfront Plaza
Lift Bridge Lodge, an Ascend Collection Hotel
Barker's Island Inn Resort
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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
$118 nightly
The price is $132 total per night from Feb 10 to Feb 11
$132 total
Feb 10 - Feb 11
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Clean room. Spacious. Easy check in.

Reviewed on Jan 28, 2026

AmericInn by Wyndham Ashland
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
$154 nightly
The price is $173 total per night from Feb 8 to Feb 9
$173 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (746 reviews)
Excellent breakfast, lovely hotel, clean and modern

Reviewed on Jan 11, 2026

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

Quality Inn Ashland - Lake Superior

2.5 out of 5
30600 Us Highway 2 Ashland WI
$92 nightly
The price is $104 total per night from Feb 22 to Feb 23
$104 total
Feb 22 - Feb 23
Total with taxes and fees
8.8/10 Excellent! (936 reviews)
This hotel feels like staying in a cabin on the lake. The room was beautifully themed but also very clean. The view out the window of the lake was spectacular. The breakfast was actually quite tasty. Loads of options and even a fun pancake machine. The staff were extremely friendly and made you feel ...

Reviewed on Jan 16, 2026

Quality Inn Ashland - Lake Superior
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, Wisconsin, is a fantastic destination for outdoor enthusiasts, offering a variety of activities including skiing and exploring scenic recreational areas. Visitors can enjoy thrilling outdoor adventures, indulge in wine tasting, and immerse themselves in local cultural experiences. Whether you're hitting the slopes or savoring regional flavors, Ashland promises a memorable vacation filled with excitement and discovery.

Shopping

In Ashland, visit the local shops along Main Street for unique gifts and souvenirs. If you're up for a drive, check out the Ashland Plaza, a shopping mall featuring various retail stores, and the nearby Chequamegon Mall, offering even more shopping options and dining experiences.

Recreation

Experience tranquility at the Northern Great Lakes Visitor Center, where nature meets relaxation. Enjoy captivating performances at StageNorth, perfect for family outings or romantic evenings. For outdoor enthusiasts, the Apostle Highlands Golf Course offers stunning views and invigorating play, making it an ideal spot for sports lovers.

Adventure

Experience thrilling skiing at Mount Ashwabay Ski and Recreation Area, located 13 miles from Ashland, perfect for adventure seekers. For water sports, try AnimAashi Sailing Company, 15 miles away, or Living Adventure, 18 miles away, both offering exhilarating outdoor activities on the beautiful waters.

Nightlife

Ashland's nightlife offers a cozy vibe with local bars and live music venues. Grab a craft beer at the South Shore Brewery or enjoy live performances at the Ashland Historical Museum. For a laid-back evening, visit the Bayfield Winery for wine tasting and scenic views of Lake Superior.

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

Find the best attractions in and around Ashland

Ashland, Wisconsin, is a fantastic destination for outdoor enthusiasts and adventure seekers. Visitors can explore historical museums, a scenic marina, and beautiful parks. Must-see attractions include Ashland Creek, Mount Ashland, and the Mount Ashland Ski Area, making it ideal for families and culture lovers alike. With its stunning scenery and diverse activities, Ashland promises a memorable experience for all types of travelers.

  • Ashland Historical Museum: Dive into the rich history and culture of Ashland at this local museum. Featuring exhibits that showcase the area's heritage, the museum offers a unique glimpse into the past, perfect for history enthusiasts and curious travelers alike.
  • Ashland Mural Walk: Enjoy a vibrant outdoor experience as you stroll through Ashland's Mural Walk. This public art display features stunning murals that reflect the city's culture, making it an ideal spot for photography and appreciating local artistry.
  • Apostle Islands Marina: Located 15 miles from Ashland, Apostle Islands Marina is a gateway to adventure. With access to beautiful beaches and water activities, it's perfect for those seeking outdoor fun, whether kayaking, sailing, or simply relaxing by the shore.

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 moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is very cloudy with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January14.7°F (-9.6°C)No RainVery CloudyModerately LowSlightly Low
February15.4°F (-9.2°C)No RainMostly CloudyAverageAverage
March28.0°F (-2.2°C)Light RainMostly CloudyAverageAverage
April38.1°F (3.4°C)Light RainMostly CloudyAverageAverage
May51.6°F (10.9°C)Light RainMostly SunnyAverageAverage
June61.5°F (16.4°C)Light RainMostly SunnyModerately HighAverage
July68.0°F (20.0°C)Light RainMostly SunnyModerately HighSlightly High
August66.9°F (19.4°C)Light RainMostly SunnyModerately HighSlightly High
September59.7°F (15.4°C)Light RainMostly SunnyAverageSlightly High
October46.2°F (7.9°C)Light RainMostly SunnyAverageAverage
November33.3°F (0.7°C)Light RainMostly CloudyModerately LowSlightly Low
December21.7°F (-5.7°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Ashland

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Ashland.
  • Consider traveling to Ashland during the low season (November to January) for more affordable options.
  • 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
Population
8,000
Max Temp Winter
20ºF
Max Temp Summer
75ºF
Top Sights
Ashland Historical Museum, Maslowski Beach and StageNorth

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Frequently asked questions

How much does an Ashland vacation package cost?
You'll find cheap prices from $728 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.

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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.