Sheboygan Vacation Rentals

Our Favorite Vacation Rentals in Sheboygan

  • BEACHSIDE GETAWAY
    Nice2br Home/Apartment
    HolidayLettings
    From
    $147
  • Lake Shore House on Lake Michigan! Dog Friendly!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $166
  • Gorgeous Lake Michigan beach Mid-Century “smart” home
     4br Home/Apartment
    HolidayLettings
    From
    $675
  • REMODELED HOUSE ON LAKE MICHIGAN
    Good3br Home/Apartment
    HolidayLettings
    From
    $465
  • REMODELED HOME OVERLOOKING LAKE MICHIGAN
     3br Home/Apartment
    HolidayLettings
    From
    $209
  • Sheboygan Surf House "The Elbow"
    ExcellentHome/Apartment
    Airbnb
    From
    $99
  • Beach and golf house
    Excellent4br Home/Apartment
    Airbnb
    From
    $297
  • Vintage Sheboygan
    Good3br Home/Apartment
    Airbnb
    From
    $145

Check prices for these upcoming dates

Sheboygan Vacation Rentals with a Pool

  • Sandhill: The Most Luxurious Way to Rough It.
     Home/Apartment
    Airbnb
    From
    $1,490

Sheboygan Vacation Rentals with Wi-Fi

  • Charming and Relaxing Bungalow Near Lake
    ExcellentBungalow
    Airbnb
    From
    $62
  • Bungalow near Lake/Kohler/PGA golf/hr to Lambeau 2
    Excellent2br Home/Apartment
    Airbnb
    From
    $123
  • Das Sheboyganhaus
     3br Home/Apartment
    Airbnb
    From
    $132
  • Little Wisconsin Getaway
    ExcellentHome/Apartment
    Airbnb
    From
    $88

Sheboygan Pet-Friendly Vacation Rentals

  • Great for Golf buddies/Couples/Family gathering
    Excellent3br Home/Apartment
    Airbnb
    From
    $268
  • Cute house in Sheboygan Falls
    Good2br Home/Apartment
    Airbnb
    From
    $167
  • Log Cabin style home on 28 acres of private land
     3br Home/Apartment
    Airbnb
    From
    $565
  • 2020 RYDER CUP...A Great place on a Great Lake!
    Excellent3br Home/Apartment
    Airbnb
    From
    $367

Sheboygan Travel Guide

Sheboygan is a wonderful place to visit for all traveler types. Sheboygan is situated in Wisconsin and is north of Milwaukee. It's a great vacation getaway for family fun, a romantic break or a long weekend with friends. Sheboygan Wisconsin is famous for being on the banks of Lake Michiganand is sure to keep you entertained for days on end.

Things to Do in Sheboygan

From outdoors adventures to culture and history, there's an impressive range of things to do when visiting Sheboygan. First on your list should be the John Michael Kohler Arts Center musem, it's a must-see and great experience for first-time travelers here. The Botanical Gardens, Bookworm Gardens, inspired by local kids is also a wonderful activity. These are of course just some of the things to do while visiting Sheboygan. This charming city has many other activities to choose from its honestly just going to depend on what you're looking for. Another popular thing to do is is the interactive play at the Above and Beyond Children's museum -- where adults and kids alike can make lasting memories!

Best Time to Visit Sheboygan

Plan a vacation to Sheboygan in the summer months when the weather is warm and the days are long -- ideal for exploring in nature.

Food in Sheboygan

The two best restaurants in Sheboygan are Trattoria Stefano, which is known for having some of the best Italian food, and the equally delicious Farm to Table.

Price and Availability in Sheboygan

Most expensive
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The cheapest day to stay at a vacation rental in Sheboygan tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Sheboygan tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Sheboygan is in July, while the cheapest month is in December. The most popular time to book a vacation rental in Sheboygan is in the high season in August. Sheboygan has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Sheboygan

Rainy days
50° 13°
2
46° 12°
2
52° -10°
1
58° -12°
1
54°
1
68° 14°
2
94° 37°
5
95° 38°
2
91° 46°
3
90° 50°
7
88° 32°
2
81° 22°
5
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Sheboygan. The warmest months in Sheboygan are July and August, when temperatures reach 95 ˚F. The coolest month is November, when temperatures drop to -12 ˚F. The wettest month in Sheboygan is May with 6.86 inches of rain, while the driest month is October with 1.17 inches of rain.

What Expert Travelers Think

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

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Vacation Rentals in Sheboygan

At AllTheRooms.com we have rentals from all of the best providers - Airbnb, Priceline, RedAwning and many more. AllTheRooms has 351 rentals, hotels and other great places to stay while you enjoy Sheboygan, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. If you are trying to save money, the lowest priced place to stay in Sheboygan is just $25 per night. An average accommodation in Sheboygan costs on average $558 per night.

If you have to have an internet connection during your time in Sheboygan, then you can choose from over 118 places to stay that have WiFi internet. 27 places to stay include a morning meal. You can keep up with your workout regime by staying at one of 12 accommodations that provide gym facilities. If you are driving to Sheboygan, you'll want to pick from 124 places to stay that provide parking. 11 accommodations come with a pool or jacuzzi

AllTheRooms has 28 pet-friendly places to stay in Sheboygan, so if you're traveling with your cat or dog you won't have any trouble.

In Sheboygan AllTheRooms currently compares hotels, vacation rentals, hostels from more than 5 providers, including 112 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from RedAwning.

147 of our accommodations in Sheboygan have been reviewed and rated. 49% are rated excellent or good. 105 places to stay in are instantly bookable.

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