Sheboygan Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Sheboygan Vacation
With a Sheboygan vacation package, discovering the best of this coastal city is simple. From its lively atmosphere and rich history to its family-friendly attractions, this destination has something for everyone to enjoy. Every trip to Sheboygan needs a well-designed itinerary. Fill yours with famous sights like Blue Harbor Resort & Conference Center Water Park, Kohler Design Center and John Michael Kohler Arts Center. Whoever you're heading away with and whatever the size of your budget, your dream Sheboygan vacation is just a few clicks away with Expedia.
Top Sheboygan Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing Apartments at Mayfair Collection
Wauwatosa
CA $1,342
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance.
We highly recommend staying here and will definitely be returning for a longer extended stay!
Reviewed on May 21, 2026
Ready to book your vacation to Sheboygan?
Sheboygan Hotel Deals
Watershed Hotel
838 N 15th St Sheboygan WI
Fully refundableReserve now, pay when you stay
CA $230
CA $260 total
Aug 23 - Aug 24
includes taxes & fees
Grandstay Residential Suites Hotel - Sheboygan
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
CA $159
CA $181 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,072 reviews)
"The area was okay, close to the downtown as well as close to the farmers market area. There was never anyone at the front desk, only a button to push when you wanted to get someones attention. Breakfast wasnt anything to write home about. It was an okay stay for the price."
Reviewed on Aug 18, 2026
AmericInn by Wyndham Sheboygan
3664 S Taylor Dr Sheboygan WI
Fully refundableReserve now, pay when you stay
CA $134
CA $152 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"The air conditioner was stuck on “on”. We had to unplug it to stop it from getting too cold. The breakfast was very simple. The room was clean and the hotel was quiet."
Reviewed on Aug 17, 2026
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.
Stay near popular Sheboygan attractions
Whistling Straits Golf Course
9.4/10 (20 reviews)
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
9.4/10 (81 reviews)
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.
Bookworm Gardens
Explore the great outdoors at Bookworm Gardens, a lovely green space in Sheboygan. Wander the lakeside and beautiful beaches in this family-friendly area.
Stefanie H. Weill Center for the Performing Arts
9.0/10 (26 reviews)
Enjoy an outing to Stefanie H. Weill Center for the Performing Arts during your stay in Sheboygan. While you're in the area, stroll along the lakeside.
Kohler Park Dunes State Natural Area
Explore the great outdoors at Kohler Park Dunes State Natural Area, a lovely green space in Sheboygan. Wander the lakeside and beautiful beaches in this family-friendly area.
Sheboygan Breakwater Lighthouse
After visiting Sheboygan Breakwater Lighthouse, make a plan to see the other sights and activities in Sheboygan. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Above & Beyond Children's Museum
8.8/10 (22 reviews)
You can take time to visit Above & Beyond Children's Museum during your travels to Sheboygan. While you're in the area, stroll along the lakeside.
Sheboygan County Historical Museum
9.4/10 (13 reviews)
You can spend time exploring the galleries in Sheboygan County Historical Museum during your travels in Sheboygan. While you're in the area, stroll along the lakeside.
What to do in Sheboygan
Sheboygan Segway Tour w/ Private Tour Option
CA $142
per adult
Private Professional Golf Experience in American Club Wisconsin
CA $303
per adult
Frequently asked questions
How much does a Sheboygan vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,103 on Expedia. However, how much your vacation to Sheboygan costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Sheboygan?
You can generally find reduced prices and greater availability in January, February and April. Browse our cheap Sheboygan vacation packages and you could get some great off-season deals.
How many days is enough for Sheboygan?
We'd recommend booking a Sheboygan vacation for at least 2 days. This will allow you time to check off key attractions including Stefanie H. Weill Centre for the Performing Arts and Above & Beyond Children's Museum, as well as check out neighbourhoods like Downtown Sheboygan and Ellis Historical District. You might even be able to make time for one or two day trips beyond Sheboygan.
Is it worth booking a vacation package to Sheboygan?
Sheboygan has all the ingredients you need for an amazing trip — family-friendly attractions, cycling and watersports are just the start. Whether you want to check out sights like Blue Harbour Resort & Conference Centre Water Park and John Michael Kohler Arts Centre, or take the road less travelled, you'll find plenty to see and do on your Sheboygan vacation.
How to find the best Sheboygan package deals?
Finding a cheap Sheboygan package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Sheboygan package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Sheboygan vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can personalize your Sheboygan trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Sheboygan?
If you've got your Sheboygan vacation dates confirmed, book early to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Sheboygan?
- Pick your dates: What you'd like to do in Sheboygan and your preferred season can help you decide when to get away.
- Plan your budget wisely: On top of the cost of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Sheboygan.
- Decide how many days away: Start by compiling a list of the activities and attractions you'd like to get to in Sheboygan. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Sheboygan vacation package.
Explore a world of travel with Expedia
- Milwaukee Hotels
- Cottages in Two Rivers
- The Inn on Maritime Bay
- Port Washington Hotels
- Chilton Hotels
- Hotels near Road America
- Lake Michigan views! Complimentary housekeeping with monthly stays Mar
- Cedar Grove Hotels
- Americinn by Wyndham Manitowoc
- Blue Harbor Resort and Conference Center
- Hotels near Whistling Straits Golf Course
- Apartments in Orchard Grove
- The Oasis Hotel & Bar
- Farmstay in Manitowoc County
- B&B in New Holstein
- Manitowoc Hotels
- Baymont by Wyndham Plymouth
- Holiday Inn Manitowoc by IHG
- Harbor Town
- B&B in Cedar Grove
- Vacation Homes in Kohler
- Cabin Rentals in Elkhart Lake
- Castles in Kohler
- Cabin Rentals in Collins
- Motels in Ozaukee County
- Sheboygan Hotels
- Kohler Hotels
- Kiel Hotels
- The Esker Ridge Chalet
- Resorts in Wells
- Saukville Hotels
- Sheboygan Falls Hotels
- Harbor Winds Hotel
- Apartment near many locations.
- Beach Hotel Hotels in Two Rivers
- Romantic Hotels in Manitowoc
- Belgium Hotels
- Pristine Beach Access
- The Osthoff Resort
- Hotels near Stefanie H. Weill Center for the Performing Arts
- Unique Rustic Industrial Ryder Cup Rental…
- The Rochester Inn
- Plymouth Hotels
- Inn On Woodlake
- Guest Houses in Manitowoc
- Inviting
- Hotels with Hot Tubs in Sheboygan
- 4 Star Hotels in Manitowoc
- Resorts in Cranberry Marsh
- Historic Hotels in Plymouth
- Waterpark Hotels in Two Rivers
- Flights from Toronto (YYZ) to Manitowoc (MTW)
- Flights from Flint (FNT) to Manitowoc (MTW)
- Flights from Indiana (IDI) to Sheboygan (SBM)
- Flights from Valders
- Flights from Chicago (ORD) to Sheboygan (SBM)
- Flights from Toronto (YYZ) to Milwaukee (MKE)
- Flights from Detroit (DTW) to Manitowoc (MTW)
- Flights from Toronto (YYZ) to Green Bay (GRB)
- Flights to Saukville
- Flights from Two Rivers
- Flights to Kohler
- Flights from Kohler
- Flights from Toronto (YTZ) to Manitowoc (MTW)
- Flights from Elkhart Lake
- Flights to Two Rivers
- Flights to Plymouth
- Flights to Belgium
- Flights to Elkhart Lake
- Flights from Portland (PDX) to Manitowoc (MTW)
- Flights to Sheboygan Falls
- Flights from New York (NYC) to Manitowoc (MTW)
- Flights to Sheboygan
- Flights from Mesa (AZA) to Manitowoc (MTW)
- Flights from Columbus (CMH) to Sheboygan (SBM)
- Flights from Sheboygan
- Flights from Minneapolis (MSP) to Sheboygan (SBM)
- Flights to Manitowoc
- Oshkosh Vacations
- Discovery World
- Visit Elkhart Lake
- Milwaukee Vacations
- Basilica of Saint Josaphat
- Kimberly Vacations
- Visit Johnsonville
- Milwaukee City Hall
- Green Bay Vacations
- Wisconsin Vacations
- Brookfield Square Mall
- Visit Newburg
- Lambeau Field
- Belgium Vacations
- Mitchell Park Horticultural Conservatory
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
