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

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 Lake House on the Shores of Erler Lake.

Beautiful 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 Eisenbahn State Trail.
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
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
REMODELED HOME ON LAKE MICHIGAN

REMODELED HOME ON LAKE MICHIGAN

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be on a lake, just steps from Lake Michigan and a 2-minute drive from St. Peter Claver Parish.
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
The price is AU$508 per night from 17 Apr to 18 Apr
AU$508
includes taxes & fees
17 Apr - 18 Apr
When you stay at this vacation home in Two Rivers, you'll be on the waterfront, just steps from Lake Michigan and 8 minutes by foot from Mariners Trail & Rawley ...
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
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!
Riverfront Getaway

Riverfront Getaway

Two Rivers
With a stay at this vacation home, you'll be centrally located in Two Rivers, within a 5-minute drive of Lake Michigan and Rogers Street Fishing Village.
Riverfront Getaway
Two Rivers ‘Thiede House’ - Walk to Lake Michigan!

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

Two Rivers
With a stay at this vacation home in Two Rivers, you'll be within a 5-minute walk of Lake Michigan and Mariners Trail & Rawley Point Bike Trails.
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
With a stay at this vacation home in Two Rivers, you'll be within a 10-minute drive of Lake Michigan and Bernard Schwartz House.
Charming 3-bedroom dog friendly home on 5 acres in Two Rivers. Lambeau Field
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
291 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$508
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 AU$199 per night from 6 Apr to 7 Apr
AU$199
includes taxes & fees
6 Apr - 7 Apr
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
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$137 per night from 6 Apr to 7 Apr
AU$137
includes taxes & fees
6 Apr - 7 Apr
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$141 per night from 6 Apr to 7 Apr
AU$141
includes taxes & fees
6 Apr - 7 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
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$296 per night from 16 Apr to 17 Apr
AU$296
includes taxes & fees
16 Apr - 17 Apr
With a stay at Watershed Hotel in Sheboygan, you'll be within a 5-minute drive of Lake Michigan and Stefanie H. Weill Center for the Performing Arts.
Watershed Hotel
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.