Photo by ed lee schneider

Sheboygan Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Sheboygan

Lobby
Grandstay Residential Suites Hotel - Sheboygan
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (982)
"Nice hotel and area. Walked less than a block to a wonderful restaurant."
$108 nightly
The price is $123
Oct 27 - Oct 28
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
Fridge, microwave, oven, stovetop
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, (251)
"Minutes from Blue Harbor & River complex of shops, restaurants & beaches. Sweet lake view from private back yard. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Fridge, microwave, oven, stovetop
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
10.0 out of 10, Exceptional, (118)
"We had 10 people staying at this property. Plenty of space for all of us. So close to the beaches. Beautiful view of Lake Michigan. "
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Fireplace, books
Beach front luxury spacious villa !
Beach front luxury spacious villa !
10.0 out of 10, Exceptional, (69)
"Wonderful view, great time!"
Beach front luxury spacious villa !
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (20)
"Top notch, close to everything you want in Sheboygan "
$115 nightly
The price is $131
Oct 19 - Oct 20
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Terrace/patio
Lakeview Farm | Beach · Hot Tub · Theater · 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
Marina
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
10.0 out of 10, Exceptional, (108)
"Great stay close to marina and restaurants "
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Interior
BEACHSIDE GETAWAY IN SHEBOYGAN
BEACHSIDE GETAWAY IN SHEBOYGAN
10.0 out of 10, Exceptional, (26)
"Our stay was really good. The location of the property was definitely the biggest reason we booked. Easy walking beach access. You have a nice view of the beach from the front and back of the property. The inside was cute and cozy. "
BEACHSIDE GETAWAY IN SHEBOYGAN
Fridge, microwave, oven, stovetop
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
10.0 out of 10, Exceptional, (3)
"Awesome place, we loved it!"
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
Property grounds
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
10.0 out of 10, Exceptional, (187)
"We had a lovely stay! Beautiful view and loved the hot tub! "
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.8 out of 10, Exceptional, (6)
"We found this location to be the perfect balance during our stay. We were a short drive away from all the places we hoped to go. Downtown, shopping, and the coast were just minutes away. Despite this luxury, the neighborhood we were in was quiet, private and removed from the hustle of crowds and traffic. The property was very well cared for and beautifully decorated. We all had plenty of room to stretch out and prepare for an event we were attending. Grabbing a snack or a meal was a breeze with...
$163 nightly
The price is $185
Oct 20 - Oct 21
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior
Edgewater Escape: 4 Bedroom, Sleeps 14!
Edgewater Escape: 4 Bedroom, Sleeps 14!
$553 nightly
The price is $627
Oct 16 - Oct 17
Total with taxes and fees
Edgewater Escape: 4 Bedroom, Sleeps 14!
Sun loungers, beach towels
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
10.0 out of 10, Exceptional, (21)
"Beautiful, clean accommodations- walkable to the beach- plenty of towels- owners were very prompt at answering questions- would stay again"
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Outdoor dining
Malibu of the Midwest Condo steps from the Lake
Malibu of the Midwest Condo steps from the Lake
10.0 out of 10, Exceptional, (65)
"Wonderful accommodations with so much to enjoy locally (Lake Michigan, beach, State Parks, breweries, farmer’s markets, etc.) but also with easy access to Door County and Milwaukee. "
Malibu of the Midwest Condo steps from the Lake
Terrace/patio
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan
10.0 out of 10, Exceptional, (2)
"Great place to stay. The lake views were amazing!"
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan
On the beach
Beachside Condo w/ Stunning Lake Views
Beachside Condo w/ Stunning Lake Views
10.0 out of 10, Exceptional, (23)
"Condo was just as pictured, loved the views from the balconies in this upper unit! Location was perfect with the beach and park within steps, the kids (ages 3-10) loved it. Everything needed to enjoy the beach being provided was very helpful. Also very close to restaurants and other things to check out. Looking forward to returning again! "
Beachside Condo w/ Stunning Lake Views
Property grounds
REMODELED HOME ON LAKE MICHIGAN
REMODELED HOME ON LAKE MICHIGAN
9.8 out of 10, Exceptional, (158)
"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
Fridge, microwave, oven, stovetop
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
2.0 star property
10.0 out of 10, Exceptional, (11)
"Wonderful property! Outstanding, thoughtful accommodations and hosts! Highly recommend and definitely would stay again. They really tried to help with everything and were successful in making our stay overwhelmingly positive! Thank you Bryan and Anja!"
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Exterior detail
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
9.8 out of 10, Exceptional, (11)
"We really enjoyed our stay at this property. The location was great for our trip to Road America racetrack. Very clean home with updated everything! Thank you so much!!"
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Interior
Lake Breeze on 11th
Lake Breeze on 11th
9.2 out of 10, Wonderful, (7)
"We had a great time here. The kids loved the little toy room. We highly recommend this stay when traveling with littles. "
Lake Breeze on 11th
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheboygan Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent
"Nice and clean"
Roland Young 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott 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, 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 $123 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.

Explore a world of travel with Expedia

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?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! 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.