Ashland Vacations from $434
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The Latest Ashland Vacation Packages
- AmericInn by Wyndham Duluth South Black Woods Event Center
Sep 4 - Sep 7AmericInn by Wyndham Duluth South Black Woods Event Center + Flight
Duluth3 nights3.0 star property8.8/10 - Excellent (1,001 reviews)"Our stay at the American Inn was great. The rooms were very spacious and clean. But our beds were a little too firm for us. This place would be on our radar for our next visit."Reviewed August 1, 2026Roundtrip • Minneapolis (MSP) - Duluth (DLH)MSP - DLH • Nonstop DLH - MSP • Nonstop$506$434found 1 day agoper traveler - The Lakeview Guesthouse
Sep 16 - Sep 22The Lakeview Guesthouse + Flight
Downtown Duluth6 nights2.0 star property8.8/10 - Excellent (37 reviews)"Beautiful space and decor but Microwave didn’t work, dishwasher still had dirty dishes inside from previous residents when we arrived, extremely loud ac."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Duluth (DLH)BOS - DLH • 1 stop DLH - BOS • 1 stop$1,377$1,131found 1 day agoper traveler - The Oliver Inn | Duluth Hotel Near Canal Park
Oct 8 - Oct 12The Oliver Inn | Duluth Hotel Near Canal Park + Flight
Downtown Duluth4 nights3.0 star property9.0/10 - Wonderful (463 reviews)"The parking was tricky to figure out and the are was a little sketchy. Room was large , comfy and cute"Reviewed August 1, 2026Roundtrip • Boston (BOS) - Duluth (DLH)BOS - DLH • 1 stop DLH - BOS • 1 stop$1,393$1,160found 1 day agoper traveler - Days Inn by Wyndham Duluth Lakewalk
Sep 16 - Sep 22Days Inn by Wyndham Duluth Lakewalk + Flight
Endion6 nights2.0 star property7.4/10 - Good (1,001 reviews)"It was exactly what we were thinking."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Duluth (DLH)BOS - DLH • 1 stop DLH - BOS • 1 stop$979$817found 1 day agoper traveler - Super 8 by Wyndham Superior WI
Sep 4 - Sep 7Super 8 by Wyndham Superior WI + Flight
Superior3 nights2.0 star property8.6/10 - Excellent (752 reviews)"Clean rooms , comfy beds , great shower pressure."Reviewed August 2, 2026Roundtrip • Minneapolis (MSP) - Duluth (DLH)MSP - DLH • Nonstop DLH - MSP • Nonstop$516$442found 1 day agoper traveler
Discover the most popular places to visit in Ashland
Ashland Hotel Deals
Lakeside Motel
Lakeside Motel
Hotel Chequamegon, BW Signature Collection
Hotel Chequamegon, BW Signature Collection
Cobblestone Inn & Suites - Ashland
Cobblestone Inn & Suites - Ashland
Quality Inn Ashland - Lake Superior
Quality Inn Ashland - Lake Superior
Frequently Asked Questions
How much does an Ashland vacation package cost?
You'll find cheap prices from $434 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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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.
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.
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.