Sheboygan holiday rentals

We found 420 holiday rentals — enter your dates for availability
Select from 95 houses, 25 flats and other holiday rentals to find the perfect place for your stay in Sheboygan. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Sheboygan

Showing deals for:29 Jan - 5 Feb

Four-season room w/ bar seating, great for gathering year-round.
Exceptional
(57 reviews)

Hot Tub | Beach Access near Kohler-Andrae

Oostburg

11% off
S$7,116
for 7 nights, 1 cabin
S$1,017 per night
includes taxes & fees
Hot Tub | Beach Access near Kohler-Andrae
Interior
Exceptional
(47 reviews)

Amazing Luxury Mansion ~ Indoor Pool ~ Stunning Lake Views ~ One Of A Kind!

Newton

12% off
S$34,942
for 7 nights, 1 home
S$4,992 per night
includes taxes & fees
Amazing Luxury Mansion ~ Indoor Pool ~ Stunning Lake Views ~ One Of A Kind!
Open living space gives everyone room to relax together by the fire.
Exceptional
(23 reviews)

1-Mile to Road America, 2-Miles to Elkhart Lake

Elkhart Lake

12% off
S$9,322
for 7 nights, 1 cabin
S$1,332 per night
includes taxes & fees
1-Mile to Road America, 2-Miles to Elkhart Lake
Beach
Exceptional
(109 reviews)

Beach front luxury spacious villa !

Sheboygan

7% off
S$3,493
for 7 nights, 1 villa
S$499 per night
includes taxes & fees
Beach front luxury spacious villa !
Your new favorite indoor coffee spot.
Exceptional
(14 reviews)

Modern | Beachfront | Sleeps 10

Oostburg

12% off
S$8,267
for 7 nights, 1 home
S$1,181 per night
includes taxes & fees
Modern | Beachfront | Sleeps 10
Private kitchen
Exceptional
(27 reviews)

Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake

Elkhart Lake

12% off
S$10,309
for 7 nights, 1 home
S$1,473 per night
includes taxes & fees
Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake
Firepit area perfect for evening conversations & unwinding outdoors.
Exceptional
(99 reviews)

Rare Find! Huge Beach & Luxe Woodsy Cabin

Oostburg

10% off
S$4,729
for 7 nights, 1 cabin
S$676 per night
includes taxes & fees
Rare Find! Huge Beach & Luxe Woodsy Cabin
Fully stocked and appointed kitchen for hosting groups.
Exceptional
(14 reviews)

Sheboygan Shores

Sheboygan

7% off
S$3,670
for 7 nights, 1 home
S$524 per night
includes taxes & fees
Sheboygan Shores
Breakfast area framed by forest & lake views for peaceful mornings.
Exceptional
(32 reviews)

Pristine Beach Access, Arcade near Kohler-Andrae

Oostburg

10% off
S$3,625
for 7 nights, 1 cottage
S$518 per night
includes taxes & fees
Pristine Beach Access, Arcade near Kohler-Andrae
Pool
Exceptional
(42 reviews)

Road America Adjacent Lake House with indoor pool

Plymouth

8% off
S$7,176
for 7 nights, 1 home
S$1,025 per night
includes taxes & fees
Road America Adjacent Lake House with indoor pool
Living area
Exceptional
(8 reviews)

Lake House-Kayaks/Paddle Boards/Private Pier

Plymouth

11% off
S$5,462
for 7 nights, 1 home
S$780 per night
includes taxes & fees
Lake House-Kayaks/Paddle Boards/Private Pier
Relax enjoying the view and privacy.
Exceptional
(9 reviews)

Experience Gracious Living & Destination Kohler

Sheboygan Falls

9% off
S$13,326
for 7 nights, 1 home
S$1,904 per night
includes taxes & fees
Experience Gracious Living & Destination Kohler
View of the back entry walkway leading toward the lakefront area.
Exceptional
(22 reviews)

Private Beach, Pool & Full-Kitchen

Elkhart Lake

11% off
S$2,018
for 7 nights, 1 apartment
S$288 per night
includes taxes & fees
Private Beach, Pool & Full-Kitchen
Front Deck
Exceptional
(29 reviews)

Lime Ridge Guest House

Elkhart Lake

13% off
S$3,665
for 7 nights, 1 home
S$524 per night
includes taxes & fees
Lime Ridge Guest House
Living area
Exceptional
(11 reviews)

Peaceful 4 BDRM Lake Michigan Retreat - Perfect for Friends and Families

Sheboygan

7% off
S$4,694
for 7 nights, 1 home
S$671 per night
includes taxes & fees
Peaceful 4 BDRM Lake Michigan Retreat - Perfect for Friends and Families
North deck provides a great place for morning coffee and great views of the beach front.
Exceptional
(44 reviews)

Beachside Condo w/ Stunning Lake Views

Sheboygan

11% off
S$2,117
for 7 nights, 1 apartment
S$302 per night
includes taxes & fees
Beachside Condo w/ Stunning Lake Views
Great room viewed from the loft
Exceptional
(66 reviews)

Cozy Cabin in the Woods with fishing and golf nearby

Valders

23% off
S$1,979
for 7 nights, 1 home
S$283 per night
includes taxes & fees
Cozy Cabin in the Woods with fishing and golf nearby
Open concept living and dining room
Exceptional
(18 reviews)

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth

8% off
S$3,298
for 7 nights, 1 home
S$471 per night
includes taxes & fees
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Enjoy your favorite beverage on the front porch.
Exceptional
(7 reviews)

Steps from Lake Michigan: North Point Place

Sheboygan

11% off
S$2,462
for 7 nights, 1 home
S$352 per night
includes taxes & fees
Steps from Lake Michigan: North Point Place
Terrace/patio
Exceptional
(91 reviews)

Walk to Road America Races. Enjoy the lake frontage and fishing and kayaking.

Plymouth

8% off
S$7,089
for 7 nights, 1 home
S$1,013 per night
includes taxes & fees
Walk to Road America Races. Enjoy the lake frontage and fishing and kayaking.
Dining
Exceptional
(8 reviews)

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan

8% off
S$1,512
for 7 nights, 1 home
S$216 per night
includes taxes & fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Breakfast bar offers a cozy spot to chat while meals come together.
Exceptional
(18 reviews)

Beachside, Chefs Kitchen, High-End Everything

Sheboygan

10% off
S$3,614
for 7 nights, 1 home
S$516 per night
includes taxes & fees
Beachside, Chefs Kitchen, High-End Everything
Tasteful lake-inspired color palette adds calm, inviting vibes.
Exceptional
(8 reviews)

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan

10% off
S$5,795
for 7 nights, 1 home
S$828 per night
includes taxes & fees
Walk to Beach & Pier | Fully-Loaded Kitchen
Private kitchen
Exceptional
(81 reviews)

Beach and Golf House

Sheboygan

7% off
S$3,716
for 7 nights, 1 home
S$531 per night
includes taxes & fees
Beach and Golf House
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the waterfront setting in Sheboygan

The area's museums and art galleries are just some of the reasons to come on holiday to Sheboygan. Renowned for its lake, beaches and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Sheboygan

Are you hoping to find attractions to visit while you're in the area? Venture out of your holiday home and check out everything that makes Sheboygan a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Blue Harbor Resort & Conference Center Water Park (0.4 mi / 0.6 km)
  • Blackwolf Run (3.5 mi / 5.6 km)
  • The Bull at Pinehurst Farms Golf Course (5.7 mi / 9.1 km)
  • Whistling Straits Golf Course (7.1 mi / 11.4 km)
  • Road America (14.2 mi / 22.9 km)
  • Evergreen Golf Course (12.3 mi / 19.8 km)

Exploring the beaches and other natural features in Sheboygan

Travellers enjoy Sheboygan for its lakeside setting and riverfront. Whether you're an outdoor enthusiast or just want to appreciate the scenery, Sheboygan is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Bookworm Gardens (2.2 mi / 3.5 km)
  • Elkhart Lake (16.4 mi / 26.5 km)
  • Wilke Lake (19.5 mi / 31.4 km)
  • North Side Municipal Beach (0.6 mi / 1 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • Dairyland Park (11.8 mi / 19 km)

Seasonal weather averages in Sheboygan

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Frequently asked questions

What is the best area to stay in Sheboygan when booking a holiday rental?
Ellis Historical District is among the more sought-after locations for a holiday home in Sheboygan. Spend your getaway here to enjoy all the convenience and privacy that comes with having a place to yourself.
What is the most popular type of holiday rental accommodation in Sheboygan?
Condos are the most popular style of holiday rental in Sheboygan, according to our data. Even if you have something else in mind, Vrbo has holiday homes in many shapes and sizes. Browse our many options to find your perfect fit.
How much does it cost to rent a holiday rental in Sheboygan?
A range of things influence what you'll pay for your holiday rental in Sheboygan, such as the season, length of stay and type of property. Still, all of our holiday homes have something in common — exceptional value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Sheboygan?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Sheboygan travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the features and amenities you want.
Are there pet-friendly holiday rentals in Sheboygan?
With 42 properties that allow pets, your happy hound can also come along on your Sheboygan holiday. Use the filter tool to search our pet-friendly holiday rentals and find a stay that's pawfect on Vrbo.
What are popular rental amenities in Sheboygan?
A water view, a lake view and tennis are the most popular rental amenities in Sheboygan. Whether you're taking a trip by yourself, with your significant other or as a family group, Vrbo will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday rentals in Sheboygan?
Sheboygan has two holiday rentals that can fit 10 or more people. These stays come with the privacy and space you need to enjoy good times with your nearest and dearest.
Are there holiday rentals in Sheboygan that welcome kids?
With 42 family-friendly holiday properties to select from in Sheboygan, now is a superb time to introduce your little ones to the excitement of travel. Check our "Properties good for families" filter box to look for stays that feature amenities ideal for holidaying families, like full kitchens, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in Sheboygan?
Keeping the kids happy during your Sheboygan holiday is child's play with these awesome family-friendly attractions:
  • Blue Harbour Resort & Conference Centre Water Park
  • Sheboygan County Historical Museum
  • Childrens Museum
Can I find two-bedroom holiday rentals in Sheboygan?
Gather your loved ones and enjoy a relaxing escape in one of the 15 two-bedroom holiday rentals Sheboygan has to offer.
Are there holiday rentals with WiFi in Sheboygan?
Pick from 20 holiday rentals with WiFi in Sheboygan. If you want to disconnect from daily life on your trip, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Sheboygan?
There are 42 Vrbo holiday homes with air conditioning in Sheboygan providing that cooling breeze and extra comfort level. Simply enter your travel dates and then use our filter tool to help you find properties with air conditioning.
How old do you have to be to rent a holiday rental in Sheboygan?
The minimum required age is generally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Sheboygan holiday home before you book.
How long can I rent a holiday rental in Sheboygan for?
The amount of time you can stay in a Sheboygan holiday rental for is down to the property. Simply enter your dates of travel to browse available options offering extended stays. They have all you require to make your extended trip more convenient and enjoyable, like air conditioning and kitchens. Some Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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