Book Holiday Homes in Sheboygan

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Sheboygan

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
Located in Waldo, this vacation home is within a 15-minute drive of Evergreen Golf Course and Sheboygan County Fairgrounds.
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Oostburg
With a stay at this vacation home in Oostburg, you'll be on the beach, within a 10-minute drive of Lake Michigan and Oostburg Public Library.
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
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
Save an average of 15% on thousands of hotels when you're signed in
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

Campbellsport
When you a stay at this vacation home in Campbellsport, you'll be on the waterfront, just steps from Kettle Moraine State Forest and Tittle lake.
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan
The price is AU$605 per night from 24 Nov to 25 Nov
AU$605
includes taxes & fees
24 Nov - 25 Nov
When you stay at this vacation home in Sheboygan, you'll be near the beach, within a 10-minute walk of Lake Michigan and Above & Beyond Children's Museum.
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
4 Bedroom Beachfront Condo - Fantastic Lake View

4 Bedroom Beachfront Condo - Fantastic Lake View

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be on the beach, within a 5-minute walk of Lake Michigan and Blue Harbor Resort & Conference Center ...
4 Bedroom Beachfront Condo - Fantastic Lake View
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
When you stay at this vacation home in Sheboygan, you'll be on the waterfront, just steps from Lake Michigan and a 2-minute drive from St. Peter Claver ...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!

Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!

Oostburg
With a stay at this vacation home in Oostburg, you'll be on the waterfront, within a 15-minute drive of Lake Michigan and The Bull at Pinehurst Farms Golf ...
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!
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 within a 5-minute drive of Lake Michigan and Sheboygan Indian Mound Park.
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Don't see what you're looking for?
See all available properties in Sheboygan
View all properties
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
235 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$605
Popular accommodation
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!, Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room, Welcome to the "Lake Cottage" where lake Michigan waves are calling, Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun, Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city, 4 Bedroom Beachfront Condo - Fantastic Lake View , Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!, Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!, 2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Top trending hotels in 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$148 per night from 29 Nov to 30 Nov
AU$148
includes taxes & fees
29 Nov - 30 Nov
With a stay at AmericInn by Wyndham Sheboygan in Sheboygan, you'll be in a shopping district, within a 10-minute drive of Lake Michigan and Deer Trace Mall.
AmericInn by Wyndham 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$149 per night from 24 Nov to 25 Nov
AU$149
includes taxes & fees
24 Nov - 25 Nov
With a 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 HSHS St. Nicholas ...
La Quinta Inn by Wyndham Sheboygan
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

3 out of 5
725 Blue Harbor Drive, Sheboygan, WI
The price is AU$297 per night from 24 Nov to 25 Nov
AU$297
includes taxes & fees
24 Nov - 25 Nov
When you stay at Blue Harbor Resort and Conference Center in Sheboygan, you'll be on the beach, within a 5-minute drive of Stefanie H. Weill Center for the Performing ...
Blue Harbor Resort and Conference Center
Save an average of 15% on thousands of hotels when you're signed in
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$190 per night from 24 Nov to 25 Nov
AU$190
includes taxes & fees
24 Nov - 25 Nov
With a stay at Grandstay Residential Suites Hotel - Sheboygan in Sheboygan (Downtown Sheboygan), you'll be within a 15-minute walk of Lake Michigan and Above ...
Grandstay Residential Suites Hotel - Sheboygan
Don't see what you're looking for?
See all available properties in Sheboygan
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.