Photo by ed lee schneider

Sheboygan Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (960)
"Location and ease of parking were great!"
The price is CA $184
CA $209 total
includes taxes & fees
Oct 1 - Oct 2
Grandstay Residential Suites Hotel - Sheboygan

Lake Michigan Home with gorgeous views, great spot for family or golf retreat

10.0 out of 10, Exceptional, (113)
"We had a great girls weekend at the house. We were able to walk to pickleball courts and enjoy a campfire by the lake. "
Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (248)
"We really enjoyed our stay. Very clean and easy check in process. Would highly recommend to anyone considering staying here. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Beach front luxury spacious villa !

10.0 out of 10, Exceptional, (66)
"Wonderful stay in a beautiful area, we hope to be back!! "
Beach front luxury spacious villa !

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

9.6 out of 10, Exceptional, (11)
"My fiancé and I stayed here for the motoamerica weekend at road america. Great location if you’re looking for something last minute on the cheaper side. The apartment itself was just as pictured. Perfect for just a one night stay. If I had to complain about something, it would be that the bed was pretty uncomfortable. Other than that, we had a great time. Highly recommend ordering takeout from china star! "
The price is CA $131
CA $179 total
includes taxes & fees
Sep 2 - Sep 3
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Vacation Paradise: 4 Bedroom, Sleeps 14!

2.0 star property
7.0 out of 10, Good, (4)
"Beautiful location."
Vacation Paradise: 4 Bedroom, Sleeps 14!

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

10.0 out of 10, Exceptional, (101)
"Excellent location, very comfortable and clean. "
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

BEACHSIDE GETAWAY IN SHEBOYGAN

10.0 out of 10, Exceptional, (25)
"We were up there racing in MotoAmerica. Was close to the track and was perfect for our stay."
BEACHSIDE GETAWAY IN SHEBOYGAN

Edgewater Escape: 4 Bedroom, Sleeps 14!

The price is CA $405
CA $862 total
includes taxes & fees
Sep 17 - Sep 18
Edgewater Escape: 4 Bedroom, Sleeps 14!

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

9.8 out of 10, Exceptional, (8)
"This was our first VRBO stay. It beats any hotel stay in recent memory. The amenities exceeded our expectations. Can't wait to visit again using VRBO!"
The price is CA $235
CA $555 total
includes taxes & fees
Sep 1 - Sep 2
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10.0 out of 10, Exceptional, (4)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
The price is CA $171
CA $292 total
includes taxes & fees
Sep 4 - Sep 5
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

10.0 out of 10, Exceptional, (2)
"All of us, ages 5-75 had a wonderful time. Plenty of activities but also places to relax. We especially enjoyed the beautiful yard, the pool and spa & the well equipped kitchen."
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

Beachside Condo w/ Stunning Lake Views

10.0 out of 10, Exceptional, (21)
"Beautiful location and accommodations"
Beachside Condo w/ Stunning Lake Views

Lakeview Farm | Beach · Hot Tub · Theater · Views

10.0 out of 10, Exceptional, (1)
"Fun time! Very buggy by the lake but not much you can do about that. "
Lakeview Farm | Beach · Hot Tub · Theater · Views

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

10.0 out of 10, Exceptional, (1)
"We had an awesome time!! The hosts answered all of our questions fast and helped us know things about the area. We would love to go back!"
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

Modern South Pier Condo on Sheboygan River!

9.4 out of 10, Exceptional, (28)
"Excellent place and location "
Modern South Pier Condo on Sheboygan River!

3 Bedroom Beach House

9.4 out of 10, Exceptional, (14)
"In town for Road America event, house was spacious, cozy and comfortable. Very well kept and clean!"
3 Bedroom Beach House

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (156)
"Beautiful, clean house with spectacular views of Lake Michigan. If we are ever back in the area, we will be staying here, again!"
REMODELED HOME ON LAKE MICHIGAN

Beach House on the shores of Lake Michigan Near downtown Sheboygan

10.0 out of 10, Exceptional, (4)
"Wonderful beach house right on the sandy beach!"
Beach House on the shores of Lake Michigan Near downtown Sheboygan

Family-Friendly House: Walk to Lake Michigan!

9.6 out of 10, Exceptional, (28)
"Very happy with the house we rented, it was very clean, well stocked, and great location. Definitely will recommend!"
Family-Friendly House: Walk to Lake Michigan!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sheboygan Hotel Reviews

Find out more about Sheboygan

Find out more about Sheboygan

Everything you need to know about Sheboygan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheboygan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheboygan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheboygan vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheboygan vacation rentals we have selected for you start as low as CA $131 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheboygan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheboygan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheboygan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, or you can go with a more remote option if you want a relaxing stay. Visitors to Sheboygan speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave some time to check out the marina and museums during your trip.

What are some of the best vacation home rentals in Sheboygan?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Lake Michigan Home with gorgeous views, great spot for family or golf retreat as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 95 Expedia vacation rentals in Sheboygan for a memorable vacation.

What’s there to see and do in Sheboygan?

Enjoy the outdoors at Lake Michigan and Bookworm Gardens, or simply take in cultural attractions like John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. While here, Blue Harbor Resort & Conference Center Water Park and Kohler-Andrae State Park are other places worth a visit.

What’s a vacation rental in Sheboygan like?

A vacation rental is a private property where you can stay for a long or short time in Sheboygan. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.