Sheboygan Vacation Packages 2025/2026 from $296

Sheboygan flight + hotel vacation packages

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

Antioch Hotel & Suites

$296

per person

Nov 13 - Nov 16

found 8 hours ago

Roundtrip flight included

New York (LGA) to Milwaukee (MKE)

This hotel 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. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking.

Dubbel Dutch

Downtown Milwaukee

$457

per person

Dec 6 - Dec 8

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)

This hotel features self parking and free WiFi in public areas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in, express check-out, and luggage storage are also on offer.

Best Western Plus Milwaukee Airport Hotel & Conference Ctr

$305

per person

Dec 6 - Dec 8

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free self parking, a picnic area, and express check-in are also offered.

Kinn Guesthouse Bay View

Bay View

$407

per person

Dec 6 - Dec 8

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

Kinn Guesthouse Downtown

Downtown Milwaukee

$425

per person

Dec 6 - Dec 8

found 17 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Self parking and express check-out are also offered on site.

Top Sheboygan hotels deals

Grandstay Residential Suites Hotel - Sheboygan

708 Niagara Avenue, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$123 total

Oct 19 - Oct 20

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.

La Quinta Inn by Wyndham Sheboygan

2932 Kohler Memorial Dr, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$81 total

Oct 27 - Oct 28

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.

AmericInn by Wyndham Sheboygan

3664 S Taylor Dr, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$91 total

Nov 2 - Nov 3

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.

Comfort Inn & Suites Sheboygan I-43

3912 Motel Rd, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$86 total

Nov 3 - Nov 4

Total with taxes and fees

This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Watershed Hotel

838 N 15th St, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$210 total

Oct 14 - Oct 15

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.

Wingate by Wyndham Sheboygan

723 Center Avenue, Sheboygan, WI

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$76 total

Oct 15 - Oct 16

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. There's an indoor pool on site, and laundry facilities and free newspapers are also offered.

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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.

John Michael Kohler Arts Center

You can spend time browsing the exhibits at John Michael Kohler Arts Center during your travels in Sheboygan. Wander the lakeside in this family-friendly area.

Frequently asked questions

How much are vacation packages to Sheboygan?

Exciting adventures await in Sheboygan, with Travelocity vacation packages from as little as $296. 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.