Ashland County Vacation Packages 2025/2026

Search vacation packages deals in Ashland County's top destinations

We found this cool beaver pond on a spring hike in the Chequamegon National Forest in northern Wisconsin. #SpringtimeFun

Clam Lake

Vacations

Top Ashland County hotels deals

AmericInn by Wyndham Ashland

3009 Lakeshore Drive East, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Nov 18 - Nov 19

Total with taxes and fees

2 indoor pools, a hot tub, and a gym are all featured at this traditional hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the sauna and free perks like continental breakfast and free self parking.

Super 8 by Wyndham Ashland

1610 Lake Shore Dr W, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$142 total

Nov 19 - Nov 20

Total with taxes and fees

This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Best Western The Hotel Chequamegon

101 Lake Shore Dr W, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$130 total

Dec 1 - Dec 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

Cobblestone Inn & Suites - Ashland

818 Main Street W., Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$184 total

Nov 9 - Nov 10

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and a convenience store are also provided.

Blue Wave Inn

2521 Lake Shore Dr W, Ashland, WI

Free Cancellation

$99 nightly

$111 total

Nov 6 - Nov 7

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A coffee shop, a terrace, and a picnic area are also on offer.

A-frame Cabin w/ Private Boat Dock!

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Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

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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 are vacation packages to Ashland County?

With a Travelocity vacation package, you could be living it up in Ashland County for a mere . Hotels, flights and adventures — we've got you covered. You can save some cash just by combining your bookings together. And with all of that taken care of before you even set off, you can sit back, relax and not worry about a thing.

Where can I get the best vacation package deals for Ashland County?

It's difficult to beat Travelocity when it comes to putting together your Ashland County package deal. There are as many as 400 air carriers and 1,000,000 worldwide properties to choose from. Reserve your trip now and get ready to tick another place off your travel bucket list.

Why should I book my Ashland County vacation package with Travelocity?

The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can relax knowing you're getting the best deal available.

Can I save on my Ashland County car rental if I bundle it with a hotel or flight?

You certainly can with our Ashland County vacation packages. With one of these, there are plenty of ways to stretch your travel budget further. Combine any two or more car, flight, hotel and tour bookings and watch your savings start to grow. With a rental car, all the key sights in and around Ashland County are within your reach.

Which airport is best for Ashland County?

The major airport for Ashland County is Gogebic County Airport (IWD).

Where to stay in Ashland County: Best areas for travelers

Ashland: Consider popular stays like the Cobblestone Inn & Suites - Ashland, the Super 8 by Wyndham Ashland and the Best Western The Hotel Chequamegon. Once that's sorted, get down to the important business of exploring this destination's best attractions like Ashland Historical Museum. If you're in the mood for more exploring, Northern Great Lakes Visitor Center and Chequamegon Bay Golf Course belong on your travel itinerary.
La Pointe: Many La Pointe visitors spend their evenings at the Downtown Island Condo or the Sowl\'s Cabin, Nestled on 20 Acres on Madeline Island. Compare what's on offer and see if either are up your alley. Once you've added on a hotel to your vacation package, start planning that itinerary. Madeline Island Museum should be one of the first stops on your list.