Chequamegon Bay Vacation Packages 2025/2026 from $402

Chequamegon Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Oliver Inn

Downtown Duluth

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Duluth (DLH)

A casino and a restaurant are featured at this smoke-free hotel. Enjoy the gym and perks like free WiFi. You'll appreciate the sauna, bar/lounge, and a virtual front desk.

The Suites Hotel at Waterfront Plaza

Canal Park

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Duluth (DLH)

This hotel features 2 restaurants, an indoor pool, and a hot tub. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Harris House

East Hillside

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Duluth (DLH)

This hotel features laundry facilities. Take advantage of the free self parking.

Barker's Island Inn Resort

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Duluth (DLH)

A marina and an indoor pool are featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the gym and perks like free self parking.

Historic Cotton Mansion Duluth Boutique Hotel

Endion

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Duluth (DLH)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, a library, and luggage storage are also on offer.

Top Chequamegon Bay hotels deals

The Washburn Inn - On the Lake

123 Harbor View Drive, Washburn, WI

Free Cancellation

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A restaurant and a bar/lounge are featured at this hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Free self parking, a terrace, and a garden are also offered.

Pet friendly

Parking included

Super 8 by Wyndham Ashland

1610 Lake Shore Dr W, Ashland, WI

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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.

Pool

Hot Tub

AmericInn by Wyndham Ashland

3009 Lakeshore Drive East, Ashland, WI

Free Cancellation

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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.

On private beach

Pool

Cobblestone Inn & Suites - Ashland

818 Main Street W., Ashland, WI

Free Cancellation

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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.

Pet friendly

Parking included

Best Western The Hotel Chequamegon

101 Lake Shore Dr W, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

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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.

Pool

Breakfast included

Quality Inn Ashland - Lake Superior

30600 Us Highway 2, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

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

Pool

Hot Tub

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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.

Popular places to visit

Houghton Falls Nature Preserve

4.5/5(16 reviews)

Explore the great outdoors at Houghton Falls Nature Preserve, a lovely green space in Washburn. Wander the lakeside in this family-friendly area.

Chequamegon Bay Golf Course

4.5/5(5 reviews)

Enjoy a round of golf in Ashland at Chequamegon Bay Golf Course. Wander the lakeside in this family-friendly area.

Ashland Historical Museum

4.5/5(14 reviews)

You can spend time exploring the galleries in Ashland Historical Museum during your trip to Ashland. Wander the lakeside in this family-friendly area.

Frequently asked questions

How much are vacation packages to Chequamegon Bay?

Travelocity provides flight and hotel packages starting as low as $402. With such great deals, you'll be exploring all of Chequamegon Bay before long.

Where can I get the best vacation package deals for Chequamegon Bay?

Snapping up the perfect package deal to Chequamegon Bay couldn't be easier with Travelocity. With access to 400 airlines and 1,000,000 properties across the globe, the choice is yours when it comes to picking your hotels and flights.

Why should I book my Chequamegon Bay vacation bundle with Travelocity?

We offer round-the-clock support, superb service and a Price Match Guarantee. Life is all about the journey --- and we have incredible destinations for you to journey to in every nook and cranny of the globe. Wander with us and make your hip pocket happy.

Will I save money on my Chequamegon Bay car rental if I book it with hotels and flights?

Combining your bookings into a Chequamegon Bay vacation package will save you some serious money. Combine a car and flight; a car, hotel and flight; or a hotel and car. There's no better way to discover the greater Chequamegon Bay region than with your own rental car. You can also add experiences and activities to your Travelocity package.

Which airport is best for Chequamegon Bay?

Gogebic County Airport (IWD) is where most visitors jetting to Chequamegon Bay will land.

What is there to do in Chequamegon Bay?

You'll be happy to know Chequamegon Bay is full of wonderful photo-ops, however Houghton Falls Nature Preserve and Bayfield County Courthouse are two you shouldn't miss.