Sheboygan Vacation Rentals

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Vacation Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 out of 5
708 Niagara Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is $128 per night from Oct 4 to Oct 5
$128
per night
Oct 4 - Oct 5
Stay at this business-friendly aparthotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stefanie H. Weill Center for the ...
8.4/10 Very Good! (722 reviews)
"Beds comfy. Bathrooms need bit of TLC; outdated, rocking toilet, nothing that makes it a game changer. It is clean and suited our family gathering for funeral at nearby church."

Reviewed on Sep 17, 2023

Grandstay Residential Suites Hotel - Sheboygan
Directly on Lake Michigan! Last Minute Bookings Welcome!
Stay at this family-friendly vacation home in Sheboygan. Enjoy WiFi, onsite parking, and an in-room DVD player. Popular attractions St. Peter Claver Parish and ...
9.6/10 Exceptional! (179 reviews)
Our Trip
"We really had a nice time. The house is cozy and quaint and you can't beat the beautiful view of lake Michigan from your kitchen or master bedroom. We will definitely recommend this place to others."

Reviewed on Aug 26, 2023

Directly on Lake Michigan! Last Minute Bookings Welcome!
Beach front luxury specious condo/ villa !
Stay at this villa in Sheboygan. Enjoy WiFi, onsite parking, and 3 bathrooms. Popular attractions Blue Harbor Resort & Conference Center Water Park and John ...
10/10 Exceptional! (20 reviews)
Absolutely Perfect Weekend
"Our group was 4 couples, all related, spending an adults only weekend. Edyta was an amazing host. Very quick to respond to all inquiries prior to our stay. The condo was very well appointed and had everything we needed and some things we probably didn't need. The space was large and comfortable and ..."

Reviewed on Sep 17, 2023

Beach front luxury specious condo/ villa !

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Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!
The price is $250 per night from Sep 25 to Sep 26
$250
per night
Sep 25 - Sep 26
Stay at this condo in Sheboygan. Enjoy free WiFi, onsite parking, and a patio. Our guests praise the clean rooms in our reviews. Popular attractions Blue Harbor ...
10/10 Exceptional! (51 reviews)
"Nice big windows and deck on the water!"

Reviewed on Sep 17, 2023

Amazing downtown waterfront condo with full hook-up boat slip! Close to beach!
REMODELED HOME ON LAKE MICHIGAN
Stay at this vacation home in Sheboygan. Enjoy a water park, WiFi, and onsite parking. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (121 reviews)
Family reunion.
"Great place right on the lake and just down the street from our party! The house was clean and had everything we needed!"

Reviewed on Jul 13, 2023

REMODELED HOME ON LAKE MICHIGAN
Malibu of the Midwest Condo steps from the Lake
The price is $225 per night from Oct 1 to Oct 2
$225
per night
Oct 1 - Oct 2
Stay at this condo in Sheboygan. Enjoy free WiFi, onsite parking, and a balcony. Popular attractions Blue Harbor Resort & Conference Center Water Park and St. ...
10/10 Exceptional! (20 reviews)
Beautiful Condo
"A wonderful stay! Brand new condo with wonderful accommodations. Stocked with everything needed. Location is within walking distance to everything around South Pier and downtown. Deck was great for coffee in the morning. Host was great to work with. A great place to stay for both adults and ..."

Reviewed on Sep 16, 2023

Malibu of the Midwest Condo steps from the Lake
BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach.
Stay at this family-friendly vacation home in Sheboygan. Enjoy free WiFi, a water park, and onsite parking. Popular attractions North Side Municipal Beach and ...
9.8/10 Exceptional! (48 reviews)
Fishing trip
"We had an amazing time with a great location. This property was a great fit for us, very clean and cozy. Perfect walking distance for fishing or driving to the piers."

Reviewed on Sep 13, 2023

BEST LOCATION IN SHEBOYGAN! Watch the sunrise over Lake Michigan Steps to beach.
Cozy 2 bd home, minutes from lake Michigan
The price is $150 per night from Sep 25 to Sep 26
$150
per night
Sep 25 - Sep 26
Stay at this vacation home in Sheboygan. Enjoy WiFi, a kitchen, and 2 bedrooms. Popular attractions St. Peter Claver Parish and Blue Harbor Resort & Conference ...
7.6/10 Good! (9 reviews)
Went to son’s wedding.
"The property was nice. Clean except for floors. Beds were comfortable. TV was a bit tuff to navigate. Back yard needs cleaned a bit. We had our dog and it was nice the yard was fenced."

Reviewed on Jul 23, 2023

Cozy 2 bd home, minutes from lake Michigan
South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer.
Stay at this family-friendly condo in Sheboygan. Enjoy free WiFi, onsite parking, and an arcade/game room. Popular attractions Blue Harbor Resort & Conference ...
10/10 Exceptional! (18 reviews)
Awesome location
"Very nice condo right on the canal. Hosts were very easy to communicate with. Check in and property access was easy and convenient. Would definitely recommend staying here. I will be booking again…."

Reviewed on Sep 20, 2023

South Pier Riverwalk Condo-Steps from some of the best Sheboygan has to offer.
Edgewater Escapes - 4 bed/3 bath w/ steps to Lake
The price is $363 per night from Sep 24 to Sep 25
$363
per night
Sep 24 - Sep 25
Stay at this condo in Sheboygan. Enjoy WiFi, a patio, and a TV. Popular attractions Blue Harbor Resort & Conference Center Water Park and John Michael Kohler ...
9.2/10 Wonderful! (9 reviews)
Awesome place
"Place was great! Awesome location and lots of room."

Reviewed on Sep 18, 2023

Edgewater Escapes - 4 bed/3 bath w/ steps to Lake
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Stay at this family-friendly condo in Sheboygan. Enjoy free WiFi, a water park, and onsite parking. Popular attractions Blue Harbor Resort & Conference Center ...
9.8/10 Exceptional! (58 reviews)
Nice place. Great location.
"would definitely stay here again."

Reviewed on Sep 18, 2023

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!
Stay at this apartment in Sheboygan. Enjoy free WiFi, a water park, and onsite parking. Popular attractions North Side Municipal Beach and John Michael Kohler ...
9.4/10 Exceptional! (21 reviews)
Excellent location
"This property was in an excellent location. It had the basics and a few extras (i.e. cooler bag) that you need for functioning in a VRBO. We couldn't get the TV to work, but that was less of a concern and we did not contact the property manager about it. One of the guest bed mattresses was far superior ..."

Reviewed on Sep 8, 2023

BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!
3 Bedroom Beach House
Stay at this vacation home in Sheboygan. Enjoy free WiFi, onsite parking, and a garden. Popular attractions St. Peter Claver Parish and Blue Harbor Resort & ...
10/10 Exceptional! (3 reviews)
Perfect fit for us
"Our family of 6 were in town for an activity. This was a perfect fit. The communication with manager was great; quick response and clear understanding. Property was centrally located, had everything we needed and was well taken care of. Wish we would have stayed longer to take advantage of back yard ..."

Reviewed on Aug 18, 2023

3 Bedroom Beach House
Natural Setting Cabin close to Sheboygan/Kohler
Stay at this cabin in Sheboygan. Enjoy WiFi, 2 bathrooms, and a kitchen. Popular attractions James Tellen Woodland Sculpture Garden and St. Peter Claver Parish ...
9/10 Wonderful! (4 reviews)
Labor day weekend
"Beautyfull quiet płace nearby the lake Whery clean We recomend"

Reviewed on Sep 7, 2023

Natural Setting Cabin close to Sheboygan/Kohler
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Stay at this vacation home in Sheboygan. Enjoy free WiFi, onsite parking, and a garden. Popular attractions James Tellen Woodland Sculpture Garden and Blackwolf ...
10/10 Exceptional! (148 reviews)
Perfect for a Lake Michigan beach weekend
"This townhouse is great. It's clean, modern and updated, has good amount of space, is dog-friendly, has everything you would want or need, and you can make yourself right at home. It's very close to Kohler-Andrae State Park, and it's easy to get to places in Sheboygan. Definitely recommend for a ..."

Reviewed on Sep 5, 2023

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Stay at this apartment in Sheboygan. Enjoy onsite parking, a balcony, and a TV. Popular attractions St. Peter Claver Parish and Blue Harbor Resort & Conference ...
10/10 Exceptional! (1 review)
Had a great, relaxing stay !
"I felt is was exactly what i expected as per viewing pictures and description. Deck was an extra fun thing to be able to see Lake Michigan and watch the sunrise, we will be back !"

Reviewed on Sep 4, 2023

Sheboygan Getaway w/ Deck + On-Site Lake Access!
*NEW* Sleeps 8 & Spacious!
The price is $99 per night from Sep 24 to Sep 25
$99
per night
Sep 24 - Sep 25
Stay at this apartment in Sheboygan. Enjoy WiFi, onsite parking, and a TV. Popular attractions Sheboygan County Historical Museum and Children's Museum are located ...
10/10 Exceptional! (4 reviews)
"The property is very safe and quiet. Also it is easy to get on the high way near by. The big grocery is in the walking distance away. There are a few good restaurants within 10 minutes drive. It is around 10 minutes away to 4 black wolf run and whisting straits golf courses."

Reviewed on Sep 9, 2023

*NEW* Sleeps 8 & Spacious!
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Stay at this family-friendly vacation home in Sheboygan. Enjoy free WiFi, onsite parking, and a patio. Popular attractions Children's Museum and Stefanie H. ...
9.8/10 Exceptional! (10 reviews)
The Sloane’s
"Liked it can meet our needs very well ."

Reviewed on Sep 4, 2023

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
*NEW* Beautiful & Convenient!
The price is $121 per night from Sep 24 to Sep 25
$121
per night
Sep 24 - Sep 25
Stay at this apartment in Sheboygan. Enjoy WiFi, onsite parking, and a TV. Popular attractions Sheboygan County Historical Museum and Children's Museum are located ...
10/10 Exceptional! (3 reviews)
Sheboygan-Boat racing
"We came in for the Power Boat races it was a great time and the City was very welcoming!!"

Reviewed on Aug 29, 2023

*NEW* Beautiful & Convenient!
4 Bedroom Home on the River with Private River access
Stay at this vacation home in Sheboygan. Enjoy free WiFi, a water park, and onsite parking. Popular attractions Children's Museum and Stefanie H. Weill Center ...
9.8/10 Exceptional! (11 reviews)
Excellent choice!
"Everyine expressed awe over the property. The yard and view are very special whether waking to the sound of migrating geese or enjoying a fireside chat with friends in a beautiful backyard. All of the bedrooms are spacious and bright. Jordans responsiveness and attention to our questions was 5 star ..."

Reviewed on Sep 15, 2023

4 Bedroom Home on the River with Private River access
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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.

Other types of properties in Sheboygan you may be interested in

Travelodge by Wyndham Sheboygan

Travelodge by Wyndham Sheboygan

2 out of 5
723 Center Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
Travelodge by Wyndham Sheboygan
La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

2.5 out of 5
2932 Kohler Memorial Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
La Quinta Inn by Wyndham Sheboygan
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Sheboygan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Directly on Lake Michigan! Last Minute Bookings Welcome! : Visitors give good reviews to this Sheboygan vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill 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.

How many vacation rentals will I find in Sheboygan?

Choose from 90 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 Kohler-Andrae State Park, 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 Whistling Straits Golf Course 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.

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