Chequamegon Bay Vacation Packages 2025 from $592

Chequamegon Bay flight + hotel vacation packages

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

AmericInn by Wyndham Ashland

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Duluth (DLH)

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.

St. James Social

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Duluth (DLH)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Enjoy the sauna and free perks like continental breakfast and WiFi in public areas. A coffee shop, a grocery/convenience store, and dry cleaning are also on offer.

Blue Wave Inn

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Duluth (DLH)

This smoke-free hotel features a private beach, ski-in/ski-out access, and a restaurant. 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.

Legendary Waters Resort & Casino

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Duluth (DLH)

A casino and an indoor pool are featured at this hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Mission Springs Resort

per person

Jun 9 - Jun 12

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Duluth (DLH)

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

Top Chequamegon Bay hotels deals

Super 8 by Wyndham Ashland

1610 Lake Shore Dr W, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$101

includes taxes & fees

$90 per night

Jun 2 - Jun 3

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

The Washburn Inn - On the Lake

123 Harbor View Drive, Washburn, WI

Free Cancellation

Reserve now, pay when you stay

$111

includes taxes & fees

$99 per night

May 11 - May 12

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

Quality Inn Ashland - Lake Superior

30600 Us Highway 2, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$123

includes taxes & fees

$110 per night

May 26 - May 27

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

Cobblestone Inn & Suites - Ashland

818 Main Street W., Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$144

includes taxes & fees

$129 per night

May 10 - May 11

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

$151

includes taxes & fees

$135 per night

May 14 - May 15

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

AmericInn by Wyndham Ashland

3009 Lakeshore Drive East, Ashland, WI

Free Cancellation

Reserve now, pay when you stay

$132

includes taxes & fees

$118 per night

May 15 - May 16

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

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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.

Ashland Mural Walk

Enjoy an outing to Ashland Mural Walk during your stay in Ashland. Wander the lakeside in this family-friendly area.

Bayfield County Courthouse

Find out about the history of Washburn when you take a trip to Bayfield County Courthouse. 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 $592. 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.