Book Holiday Homes in Sheboygan

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Featured Holiday Homes in Sheboygan

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan
Stay at this vacation home in Sheboygan. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions St. Peter Claver Parish and Blue Harbor Resort ...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Beautiful Lake House on the Shores of Erler Lake.

Beautiful Lake House on the Shores of Erler Lake.

West Bend
Book a stay at this beach vacation home in West Bend. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Shalom Wildlife and St. Agnes Historic ...
Beautiful Lake House on the Shores of Erler Lake.
Welcome to the "Lake Cottage"  where lake Michigan waves are calling

Welcome to the "Lake Cottage" where lake Michigan waves are calling

Cedar Grove
Book a stay at this beach vacation home in Cedar Grove. Enjoy free WiFi, a beach locale, and a water park. Popular attractions North Beach and Harrington Beach ...
Welcome to the "Lake Cottage" where lake Michigan waves are calling
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REMODELED HOME ON LAKE MICHIGAN

REMODELED HOME ON LAKE MICHIGAN

Sheboygan
Stay at this vacation home in Sheboygan. Enjoy a water park, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
REMODELED HOME ON LAKE MICHIGAN
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

Two Rivers
Book a stay at this family-friendly vacation home in Two Rivers. Enjoy a water park, a garden, and patios. Popular attractions Mariners Trail & Rawley Point ...
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

Waldo
Stay at this vacation home in Waldo. Enjoy a pool table, patios, and an in-room coffeemaker. Popular attractions Evergreen Golf Course and Antoinette are located ...
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Riverfront Getaway

Riverfront Getaway

Two Rivers
Stay at this vacation home in Two Rivers. Enjoy free WiFi, a garden, and patios. Popular attractions Rogers Street Fishing Village and Historic Washington House ...
Riverfront Getaway
Two Rivers ‘Thiede House’ - Walk to Lake Michigan!

Two Rivers ‘Thiede House’ - Walk to Lake Michigan!

Two Rivers
Stay at this vacation home in Two Rivers. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Mariners Trail ...
Two Rivers ‘Thiede House’ - Walk to Lake Michigan!
Charming 3-bedroom dog friendly home on 5 acres in Two Rivers. Lambeau Field

Charming 3-bedroom dog friendly home on 5 acres in Two Rivers. Lambeau Field

2 out of 5
Two Rivers
Stay at this vacation home in Two Rivers. Enjoy in-room fireplaces and air conditioning. Popular attractions Bernard Schwartz House and Rogers Street Fishing ...
Charming 3-bedroom dog friendly home on 5 acres in Two Rivers. Lambeau Field
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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.

Sheboygan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sheboygan vacation homes are the perfect way for you to wing it.

Holiday houses in Sheboygan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sheboygan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sheboygan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sheboygan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sheboygan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sheboygan Holiday Homes essential information

Accommodation
291 Holiday Homes
Lowest Price
NZ$150
Highest Price
NZ$328
Popular accommodation
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!, Beautiful Lake House on the Shores of Erler Lake., Welcome to the "Lake Cottage" where lake Michigan waves are calling, REMODELED HOME ON LAKE MICHIGAN, Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr. , NEW Three bedroom ranch style pet friendly home with a patio & theatre room!, Riverfront Getaway, Two Rivers ‘Thiede House’ - Walk to Lake Michigan!, Charming 3-bedroom dog friendly home on 5 acres in Two Rivers. Lambeau Field

Top trending hotels in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 7 Apr to 8 Apr
NZ$218
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this business-friendly aparthotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Grandstay Residential Suites Hotel - Sheboygan
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

2 out of 5
3664 S Taylor Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$150 per night from 6 Apr to 7 Apr
NZ$150
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
AmericInn by Wyndham Sheboygan
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$328 per night from 4 Apr to 5 Apr
NZ$328
includes taxes & fees
4 Apr - 5 Apr
Stay at this 3-star business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Watershed Hotel
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La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

2.5 out of 5
2932 Kohler Memorial Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 6 Apr to 7 Apr
NZ$154
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this golf hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
La Quinta Inn by Wyndham Sheboygan
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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.

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^Subject to availability and chosen travel dates.