Book Holiday Homes in Sheboygan

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Featured Holiday Homes in Sheboygan

Updated Sheboygan Home w/ Porch < 1 Mi to Beach

Updated Sheboygan Home w/ Porch < 1 Mi to Beach

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be near the beach, within a 5-minute drive of Lake Michigan and Blue Harbor Resort & Conference Center ...
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
1 Block to the Beach! Firepit, 2 Bikes, Sleeps 4

1 Block to the Beach! Firepit, 2 Bikes, Sleeps 4

Two Rivers
With a stay at this vacation home in Two Rivers, you'll be within a 5-minute walk of Lake Michigan and Neshotah Park.
1 Block to the Beach! Firepit, 2 Bikes, Sleeps 4
Beautifully restored lake house on the shores of Erler Lake.

Beautifully restored lake house on the shores of Erler Lake.

West Bend
Located in West Bend, this vacation home is on the waterfront, within a 15-minute drive of Shalom Wildlife and Kettle Moraine State Forest.
Beautifully restored lake house on the shores of Erler Lake.
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Stunning custom built country home with the ultimate game room!

Stunning custom built country home with the ultimate game room!

Plymouth
Located in Plymouth, this vacation home is in a rural location, within a 10-minute drive of Antoinette and Sheboygan County Fairgrounds.
Stunning custom built country home with the ultimate game room!
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan
With a stay at this vacation home in Sheboygan, you'll be a 4-minute drive from Lake Michigan and 7 minutes from Blue Harbor Resort & Conference Center Water ...
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Cozy Cape Cod Home

Cozy Cape Cod Home

Plymouth
The price is AU$258 per night from 20 May to 21 May
AU$258
per night
20 May - 21 May
With a stay at this vacation home in Plymouth, you'll be within a 15-minute drive of Road America and Sheboygan County Fairgrounds.
Cozy Cape Cod Home
Welcome to the "Lake Cottage"  where lake Michigan waves are calling

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

Cedar Grove
With a stay at this vacation home in Cedar Grove, you'll be on the beach, within a 10-minute drive of Lake Michigan and Harrington Beach State Park.
Welcome to the "Lake Cottage" where lake Michigan waves are calling
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Brillion
With a stay at this vacation home in Brillion, you'll be on the waterfront, and 30.6 mi (49.3 km) from Lake Michigan and 26.6 mi (42.8 km) from Road ...
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!

Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!

Two Rivers
With a stay at this vacation home in Two Rivers, you'll be on a river, within a 5-minute drive of Lake Michigan and Neshotah Beach.
Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!
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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
221 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$314
Popular accommodation
Updated Sheboygan Home w/ Porch < 1 Mi to Beach, 1 Block to the Beach! Firepit, 2 Bikes, Sleeps 4, Beautifully restored lake house on the shores of Erler Lake., Stunning custom built country home with the ultimate game room!, 2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub, Cozy Cape Cod Home, Welcome to the "Lake Cottage" where lake Michigan waves are calling, Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau, Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!

Top trending hotels in Sheboygan

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 AU$137 per night from 23 May to 24 May
AU$137
per night
23 May - 24 May
When you stay at La Quinta Inn by Wyndham Sheboygan in Sheboygan, you'll be next to a golf course, within a 10-minute drive of Lake Michigan and Blue Harbor ...
La Quinta Inn by Wyndham 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 AU$252 per night from 28 May to 29 May
AU$252
per night
28 May - 29 May
With a stay at Grandstay Residential Suites Hotel - Sheboygan in Sheboygan (Downtown Sheboygan), you'll be within a 5-minute drive of Lake Michigan and Blue ...
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 AU$172 per night from 9 Jun to 10 Jun
AU$172
per night
9 Jun - 10 Jun
When you stay at AmericInn by Wyndham Sheboygan in Sheboygan, you'll be in a shopping district, within a 10-minute drive of Lake Michigan and Blue Harbor Resort ...
AmericInn by Wyndham Sheboygan
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Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is AU$314 per night from 25 May to 26 May
AU$314
per night
25 May - 26 May
With a stay at Watershed Hotel in Sheboygan, you'll be within a 5-minute drive of Lake Michigan and Blue Harbor Resort & Conference Center Water Park.
Watershed Hotel
Don't see what you're looking for?
See all available properties in 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.