Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Sheboygan vacation rentals

Cabin, Lake View | Beach

Cabin in Campbellsport

Tiki Beach Campground
3.0 star property
$99 nightly
The price is $104
Mar 14 - Mar 15
Total with taxes and fees
Tiki Beach Campground
Lobby

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1,024 reviews)
"Room was very clean and perfect for a downtown stay"
United States
Jim
$140 nightly
The price is $159
Apr 6 - Apr 7
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
Smart TV

Vacation Home in Sheboygan

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
10.0 out of 10, Exceptional, (13 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
$144 nightly
The price is $163
Mar 16 - Mar 17
Total with taxes and fees
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Dining

Apartment in Downtown Sheboygan

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
10.0 out of 10, Exceptional, (12 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
$210 nightly
The price is $239
Mar 17 - Mar 18
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Children's area

Vacation Home in Oostburg

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (125 reviews)
"Our host was warm and welcoming and our accommodations were wonderful (well appointed and decorated … every detail well thought out)."
United States
Heidi E.
$137 nightly
The price is $145
Mar 16 - Mar 17
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Living area

Apartment in Manitowoc

2nd floor loft near the lake!
9.8 out of 10, Exceptional, (16 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
$200 nightly
The price is $226
Mar 16 - Mar 17
Total with taxes and fees
2nd floor loft near the lake!
Living area

Vacation Home in Ellis Historical District

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
9.6 out of 10, Exceptional, (12 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
$135 nightly
The price is $153
Mar 14 - Mar 15
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Beach nearby, sun loungers, beach towels

Cottage in Two Rivers

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
10.0 out of 10, Exceptional, (22 reviews)
"Amazing place with exceptional hospitality. Every detail has been thoughtfully considered, from the amenities to the overall comfort. The design is beautiful, and the outdoor space offers wonderfully relaxing vibes. We’d definitely love to return—thank you for hosting us!"
United States
Aleks M.
No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
1 bedroom, WiFi

Apartment in Ellis Historical District

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (25 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
$115 nightly
The price is $131
Mar 15 - Mar 16
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Interior

Apartment in Sheboygan

*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
$380 nightly
The price is $431
Mar 22 - Mar 23
Total with taxes and fees
*NEW* Sleeps 8 & Spacious!
Exterior detail

Vacation Home in New Holstein

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
10.0 out of 10, Exceptional, (174 reviews)
"Great place would go back"
United States
William
$318 nightly
The price is $335
Mar 20 - Mar 21
Total with taxes and fees
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Bar (on property)

Villa in Elkhart Lake

First Floor Pet Friendly Queen Suite with Single Pull-out
10.0 out of 10, Exceptional, (2 reviews)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
$355 nightly
The price is $390
Mar 15 - Mar 16
Total with taxes and fees
First Floor Pet Friendly Queen Suite with Single Pull-out
Interior

Apartment in Sheboygan

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
$162 nightly
The price is $184
Mar 15 - Mar 16
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Interior

Vacation Home in Campbellsport

Gleason's Chouse
10.0 out of 10, Exceptional, (41 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
$183 nightly
The price is $193
Apr 7 - Apr 8
Total with taxes and fees
Gleason's Chouse
Smart TV, books

Apartment in Sheboygan

Newly Updated! Downtown & Shore
9.8 out of 10, Exceptional, (6 reviews)
"Clean, spacious, and quiet. "
United States
Thomas S.
$295 nightly
The price is $334
Mar 15 - Mar 16
Total with taxes and fees
Newly Updated! Downtown & Shore
Living area

Apartment in Brillion

Luxury Suites #3
10.0 out of 10, Exceptional, (1 review)
"Apartments were clean with easy access. Centrally located entertainment room was enjoyed by my granddaughter with claw machines, games, and TV. It is a newer property and still needs a few touches, like wall decor to soften the echoes. A bench outside the individual rentsls would be nice for seating, but there's a great area out back with chairs and heating if needed. "
United States
Debby
$272 nightly
The price is $298
Mar 15 - Mar 16
Total with taxes and fees
Luxury Suites #3
Exterior

Vacation Home in Elkhart Lake

The Esker Ridge Chalet, Pristine Elkhart Solitude
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
$257 nightly
The price is $271
Mar 17 - Mar 18
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
House (4 Bedrooms) | Interior

Cottage in Campbellsport

Near Hiking: Lakefront Getaway in Campbellsport!
3.0 star property
$431 nightly
The price is $453
Mar 14 - Mar 15
Total with taxes and fees
Near Hiking: Lakefront Getaway in Campbellsport!
3 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in Sheboygan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
10.0 out of 10, Exceptional, (1 review)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
$141 nightly
The price is $160
Mar 15 - Mar 16
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Private kitchen

Cabin in Fond du Lac

Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
$800 nightly
The price is $844
Mar 14 - Mar 15
Total with taxes and fees
Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
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.
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Top Sheboygan Hotel Reviews

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"quiet and good location"
Michelle 1-night trip
Posted 23 hours ago
Grandstay Residential Suites Hotel - 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 $131 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 John Michael Kohler Arts Center, 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 REMODELED HOME ON LAKE MICHIGAN 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 North Side Municipal Beach, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Stefanie H. Weill Center for the Performing Arts and Blue Harbor Resort & Conference Center Water 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.