Sheboygan Vacation Rentals

Our Favorite Vacation Rentals in Sheboygan

  • BEACHSIDE GETAWAY
    Nice2br Home/Apartment
    HolidayLettings
    From
    $171
  • NEW! Updated Sheboygan Home w/Porch<1 Mi to Beach
     3br Home/Apartment
    HolidayLettings
    From
    $334
  • Gorgeous Lake Michigan beach Mid-Century “smart” home
     4br Home/Apartment
    HolidayLettings
    From
    $675
  • Sheboygan Surf House "The Elbow"
    ExcellentHome/Apartment
    Airbnb
    From
    $107
  • Vintage Sheboygan
    Good2br Home/Apartment
    Airbnb
    From
    $168
  • Charming and Relaxing Bungalow Near Lake
    ExcellentBungalow
    Airbnb
    From
    $62
  • Bright and Beautiful Lake Escape
    Excellent2br Home/Apartment
    Airbnb
    From
    $297
  • Parkside Bungalow across park that leads to lake
    Excellent3br Home/Apartment
    Airbnb
    From
    $170

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

  • Sunny Antique Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $229
  • Kohler Golf, Spa and Road America Condo.
    Excellent3br Home/Apartment
    Airbnb
    From
    $237
  • 2015 PGA Tournament--Entire Home
     3br Home/Apartment
    Airbnb
    From
    $881
  • Woodland Creek Retreat:Bike, hike, explore, relax!
    Excellent3br Home/Apartment
    Airbnb
    From
    $184

Sheboygan Pet-Friendly Vacation Rentals

  • Log Cabin style home on 28 acres of private land
     3br Home/Apartment
    Airbnb
    From
    $565
  • A Great place on a Great Lake!
    Excellent3br Home/Apartment
    Airbnb
    From
    $339
  • Gorgeous Home 5 Minutes from Whistling Straits
    Excellent3br Home/Apartment
    Airbnb
    From
    $170
  • Classic Sheboygan
    Excellent2br Home/Apartment
    Airbnb
    From
    $168

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
88 º32
2
81 º22
5
50 º13
2
46 º12
2
52 º-10
1
58 º-12
1
54 º8
1
68 º14
2
94 º37
5
95 º38
2
91 º46
3
90 º50
7
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — 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
  • — 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

Vacation Rentals in Sheboygan

Find the perfect accommodation for your vacation at AllTheRooms.com. We compare Airbnb, Priceline, RedAwning and others. Sheboygan has 311 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A vacation in Sheboygan can be budget-friendly - the lowest price rental is available at $30 per night. An average rental in Sheboygan costs on average $360 a night.

If you have to have internet access during your stay in Sheboygan, then you can choose from over 109 places to stay that have WiFi internet. We have 20 accommodations that come with breakfast included. You can keep up with your workout routine by staying at one of 16 accommodations that provide gym facilities. If you are driving to Sheboygan, you'll want to pick from 112 places to stay that provide parking. We track 9 hotels and vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then be sure to select one of the 30 pet-friendly accommodations available.

In Sheboygan AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 5 providers, including 85 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from RedAwning.

147 accommodations in Sheboygan have been reviewed; 57% are rated excellent or good. You can instantly book any of 85 places to stay right now.

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