Sheboygan Vacation Packages 2025/2026 from $401

Sheboygan flight + hotel vacation packages

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

Cambria Hotel Milwaukee Downtown

Westown

$401

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Milwaukee (MKE)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Saint Kate - The Arts Hotel

Downtown Milwaukee

$420

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Milwaukee (MKE)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

The Iron Horse Hotel

Fifth Ward

$477

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Milwaukee (MKE)

This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and a library are also on offer.

The Pfister Hotel

Downtown Milwaukee

$475

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Holiday Inn Express Milwaukee Downtown by IHG

Downtown Milwaukee

$417

per person

Dec 27 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Milwaukee (MKE)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Top Sheboygan hotels deals

Grandstay Residential Suites Hotel - Sheboygan

708 Niagara Avenue Sheboygan WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$136 total

Dec 4 - Dec 5

Total with taxes and fees

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

Pool

Breakfast included

Watershed Hotel

838 N 15th St Sheboygan WI

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$136 total

Nov 22 - Nov 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A lobby fireplace, express check-out, and a computer station are also on offer.

Breakfast included

Pet friendly

La Quinta Inn by Wyndham Sheboygan

2932 Kohler Memorial Dr Sheboygan WI

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$87 total

Nov 24 - Nov 25

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

AmericInn by Wyndham Sheboygan

3664 S Taylor Dr Sheboygan WI

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$91 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Holiday Inn Express Sheboygan-Kohler by IHG

3823 Germaine Ave Sheboygan WI

Free Cancellation

$103 nightly

$117 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Quality Inn Sheboygan North I-43

4332 N 40th St Sheboygan WI

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$81 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like full 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

Blue Harbor Resort & Conference Center Water Park

Enjoy a fun-filled day at Blue Harbor Resort & Conference Center Water Park during your trip to Sheboygan. Wander the lakeside in this family-friendly area.

Whistling Straits Golf Course

Enjoy a round of golf in Sheboygan at Whistling Straits Golf Course. Wander the lakeside and beautiful beaches in this family-friendly area.

Stefanie H. Weill Center for the Performing Arts

You can make plans for a show at Stefanie H. Weill Center for the Performing Arts on your trip to Sheboygan. While you're in the area, stroll along the lakeside.

Frequently asked questions

How much are vacation packages to Sheboygan?

Exciting adventures await in Sheboygan, with Travelocity vacation packages from as little as $401. Including hotels and flights, these terrific deals make it a breeze to experience all corners of the globe.

How long should my Sheboygan vacation be?

Usually, 2 nights is how long most visitors spend discovering the sights of Sheboygan. Not sure if that'll be sufficient time to do all the things on your sightseeing list? Stay a couple more nights and experience everything this place has to offer.

Where can I get the best vacation package deals for Sheboygan?

Check out Travelocity. With access to 400 air carriers and a whopping 1,000,000 hotels all over the world, selecting the perfect Sheboygan package deal couldn't be easier.

Why should I purchase my Sheboygan vacation bundle with Travelocity?

Incredible savings, an abundance of enticing destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.

Can I save on my Sheboygan car rental if I book it with a hotel or flight?

With a Sheboygan vacation package, you can bundle your flight, hotel and car bookings and save some serious money. If you want to discover the best of this impressive location, why not start with Six Flags Great America? This well-known attraction is 95 mi from Sheboygan. With your own rental car, you'll be there before you know it.

Which airport is best for Sheboygan?

General Mitchell Intl. Airport (MKE), located around 55 mi south of inner Sheboygan, is most likely where you'll touch down. Your other options are Appleton Intl. Airport (ATW) (55 mi away from central Sheboygan) and Austin Straubel Intl. Airport (GRB) (55 mi away from central Sheboygan).

What is there to do in Sheboygan?

There's a certain magic in the air as you roam the streets of Sheboygan. Blue Harbor Resort & Conference Center Water Park and John Michael Kohler Arts Center are just two famous attractions that entice visitors to this wonderful city, so add them to your travel itinerary.

Where should I stay when visiting Sheboygan?

If you're searching for a place to lay your head, consider the Grandstay Residential Suites Hotel. It's the top pick for many visitors.

Where to stay in Sheboygan: Best areas for travelers

Plymouth: There's nothing better than the feeling of waking up somewhere new, especially when you have great attractions like Evergreen Golf Course right on your doorstep. Reserve a room at the Plymouth Inn and you can visit whenever you feel like it. The AmericInn by Wyndham Plymouth and the Baymont by Wyndham Plymouth are some other options in this neighborhood.
Elkhart Lake: There are many fantastic hotels around here, such as the Osthoff #1 Resort in Midwest AAA 4 Diamond Water, Golf,spa, The Osthoff Resort and the Siebkens Resort. Enjoy a comfortable night's sleep before checking out top attractions like Farmers Market.
Manitowoc: If you're someone who'd rather get a nature fix than spend hours shopping, this is for you. Enjoy an amble around West of the Lake Gardens before chilling out at one of this neighborhood's popular hotels. Recommended options include the Econo Lodge, the Baymont by Wyndham Manitowoc Lakefront and the Harbor Town Inn.