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Holiday homes in Sheboygan You’ll Love

Top-Rated Sheboygan Holiday homes for Every Budget and Style!

Looking for a holiday home in Sheboygan (Wisconsin)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $59.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Sheboygan.

We found 15 Holiday-homes in Sheboygan and the surrounding area (within 30 miles)

Luxury Villa on Lake Michigan in Sheboygan, USA

Luxury Villa on Lake Michigan

Villa in Sheboygan, Wisconsin , 811 Beachfront Drive
Luxury Villa on Lake Michigan is located in Sheboygan, just 1.4 miles from North Side Municipal Beach and 26 miles from New Holstein Historical Societ...
  • Parking

no reviews

from $52.00 Show details »

Cozy Lake Michigan Cottage on Lake Michigan-Pet Friendly! in Sheboygan, USA

Cozy Lake Michigan Cottage on Lake Michi...

Holiday home in Sheboygan, Wisconsin , 2313 Lakeshore Drive
Just a 4-minute walk from General King Park Beach and 0.7 miles from South Side Municipal Beach, Cozy Lake Michigan Cottage on Lake Michigan-Pet Frien...
  • Street parking
  • Pets allowed

no reviews

from $323.59 Show details »

Dog-Friendly Sheboygan Home - 1 Mi to Town! in Sheboygan, USA

Dog-Friendly Sheboygan Home - 1 Mi to To...

Holiday home in Sheboygan, Wisconsin
Dog-Friendly Sheboygan Home - 1 Mi to Town! offers accommodations in Sheboygan, 1.1 miles from South Side Municipal Beach and 1.2 miles from General K...
  • Parking
  • Pets allowed

Exceptional 3 Reviews 9.7

from $131.34 Show details »

A Glorious Getaway Sheboygan - Blue Harbor Condo in Sheboygan, USA

A Glorious Getaway Sheboygan - Blue Harb...

Holiday home in Sheboygan, Wisconsin , 421 Beachfront Lane
Just a 3-minute walk from South Side Municipal Beach and 0.8 miles from General King Park Beach, A Glorious Getaway Sheboygan - Blue Harbor Condo feat...
  • Parking

Superb 8 Reviews 9.3

from $491.38 Show details »

Family-Friendly House Walk to Lake Michigan! in Sheboygan, USA

Family-Friendly House Walk to Lake Michi...

Holiday home in Sheboygan, Wisconsin
Family-Friendly House Walk to Lake Michigan! offers accommodations in Sheboygan, 1.1 miles from South Side Municipal Beach and 1.3 miles from General ...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 5 Reviews 9.6

from $222.62 Show details »

Riverfront Sheboygan Townhome with Grill! in Sheboygan, USA

Riverfront Sheboygan Townhome with Grill...

Holiday home in Sheboygan, Wisconsin
Riverfront Sheboygan Townhome with Grill! offers accommodations in Sheboygan, 1.2 miles from North Side Municipal Beach and 1.3 miles from South Side ...
  • Parking

Exceptional 9 Reviews 9.8

from $203.17 Show details »

Serene Home One Block From Lake Michigan in Sheboygan, USA

Serene Home One Block From Lake Michigan

Holiday home in Sheboygan, Wisconsin , 335 Washington Court
Serene Home One Block From Lake Michigan offers accommodations in Sheboygan, 1.4 miles from General King Park Beach and a 9-minute walk from Childrens...
  • Parking
  • Family rooms

Exceptional 2 Reviews 10.0

from $297.81 Show details »

Updated Sheboygan Home with Porch Less Than 1 Mi to Beach in Sheboygan, USA

Updated Sheboygan Home with Porch Less T...

Holiday home in Sheboygan, Wisconsin
Updated Sheboygan Home with Porch Less Than 1 Mi to Beach offers accommodations in Sheboygan, 1.6 miles from General King Park Beach and a 7-minute wa...
  • Parking

no reviews

from $310.99 Show details »

Pet-Friendly Sheboygan Home 4 Mi to Lake Michigan in Sheboygan, USA

Pet-Friendly Sheboygan Home 4 Mi to Lake...

Holiday home in Sheboygan, Wisconsin
Pet-Friendly Sheboygan Home 4 Mi to Lake Michigan offers accommodations in Sheboygan, 3.6 miles from Childrens Museum and 23 miles from New Holstein H...
  • Parking
  • Pets allowed

no reviews

from $230.41 Show details »

Spacious & Peaceful Home in the heart of Sheboygan in Sheboygan, USA

Spacious & Peaceful Home in the heart of...

Holiday home in Sheboygan, Wisconsin , 713 Huron Avenue
Just a 11-minute walk from North Side Municipal Beach and half a mile from Childrens Museum, Spacious & Peaceful Home in the heart of Sheboygan featur...
  • Parking

Fabulous 5 Reviews 8.8

from $241.37 Show details »

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan in Sheboygan, USA

Pet-Friendly Sheboygan Home, 1 Mi to Lak...

Holiday home in Sheboygan, Wisconsin
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan is located in Sheboygan, just 1.8 miles from South Side Municipal Beach and a 14-minute walk from C...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 2 Reviews 10.0

from $374.39 Show details »

Family Home, 1 Block to Lake Michigan Beach! in Sheboygan, USA

Family Home, 1 Block to Lake Michigan Be...

Holiday home in Sheboygan, Wisconsin
A 2-minute walk from North Side Municipal Beach in Sheboygan, Family Home, 1 Block to Lake Michigan Beach! offers accommodations with access to a fitn...
  • Parking
  • Spa and wellness centre

no reviews

from $384.77 Show details »

Sheboygan Home with Views of Lake and Lighthouse! in Sheboygan, USA

Sheboygan Home with Views of Lake and Li...

Holiday home in Sheboygan, Wisconsin
Sheboygan Home with Views of Lake and Lighthouse! is located in Sheboygan, just 1.6 miles from Childrens Museum and 25 miles from New Holstein Histori...
  • Parking
  • Spa and wellness centre

no reviews

from $72.00 Show details »

Beautiful 3BR Home Near Lake MI in Sheboygan, USA

Beautiful 3BR Home Near Lake MI

Holiday home in Sheboygan, Wisconsin , 434 Blackstock Avenue
Beautiful 3BR Home Near Lake MI offers accommodations in Sheboygan, 1.3 miles from North Side Municipal Beach and 1.7 miles from Childrens Museum.
  • Parking

no reviews

from $308.81 Show details »

Spacious Sheboygan Home with Grill and Fire Pit! in Sheboygan, USA

Spacious Sheboygan Home with Grill and F...

Holiday home in Sheboygan, Wisconsin
Spacious Sheboygan Home with Grill and Fire Pit! is located in Sheboygan, just 5.5 miles from Childrens Museum and 22 miles from New Holstein Historic...
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $313.94 Show details »

Number of Holiday homes in Sheboygan 15
Number of guest ratings 1,598
Average price per night $257.00
Lowest price per night $59,00
Highest price per night $471,75

Top 10 Cheapest Holiday-homes in Sheboygan

Discover the Cheapest Holiday-homes in Sheboygan – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Sheboygan

Check out the Most Booked Holiday-homes in Sheboygan – Based on Guest Popularity.

Holiday homes in Sheboygan (Wisconsin), comfortable and familiar

Staying in a holiday or vacation home in Sheboygan can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Sheboygan for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Sheboygan should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com