Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

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 21 - Mar 22
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, (1,025 reviews)
"quiet and good location"
United States
Michelle
$140 nightly
The price is $159
Apr 6 - Apr 7
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
Bar (on property)

Aparthotel in Elkhart Lake

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
$596 nightly
The price is $652
Mar 22 - Mar 23
Total with taxes and fees
Victorian Inn Elkhart Lake Wisconsin
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 23 - Mar 24
Total with taxes and fees
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
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, (126 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 26 - Mar 27
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 24 - Mar 25
Total with taxes and fees
2nd floor loft near the lake!
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 23 - Mar 24
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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.
$248 nightly
The price is $281
Mar 22 - Mar 23
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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 22 - Mar 23
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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
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 22 - Mar 23
Total with taxes and fees
Luxury Suites #3
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.2 out of 10, Wonderful, (10 reviews)
"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. "
United States
Kim K.
$173 nightly
The price is $197
Mar 24 - Mar 25
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV, books

Apartment in Sheboygan

Newly Updated! Downtown & Shore
9.8 out of 10, Exceptional, (6 reviews)
"Perfect area/accommodations. Would definitely recommend them!"
United States
Elizabeth S.
$297 nightly
The price is $337
Mar 23 - Mar 24
Total with taxes and fees
Newly Updated! Downtown & Shore
Fridge, microwave, oven, stovetop

Vacation Home in Sheboygan

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
10.0 out of 10, Exceptional, (40 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
$355 nightly
The price is $403
Mar 22 - Mar 23
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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.
$286 nightly
The price is $302
Apr 16 - Apr 17
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
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 22 - Mar 23
Total with taxes and fees
First Floor Pet Friendly Queen Suite with Single Pull-out
Interior

Vacation Home in Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
9.6 out of 10, Exceptional, (10 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
$552 nightly
The price is $582
Mar 24 - Mar 25
Total with taxes and fees
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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.
$392 nightly
The price is $445
Apr 6 - Apr 7
Total with taxes and fees
*NEW* Sleeps 8 & Spacious!
Fridge, microwave, oven, stovetop

Apartment in Sheboygan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
9.8 out of 10, Exceptional, (12 reviews)
"It was an excellent place! Very comfortable, nice neighborhood, clean and exactly as described. We were very surprised and pleased with the welcome items left in the fridge! We Will definitely stay there again! "
United States
Kathy J.
$327 nightly
The price is $371
Apr 7 - Apr 8
Total with taxes and fees
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Smart TV

Vacation Home in Sheboygan

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
9.8 out of 10, Exceptional, (25 reviews)
"Great location!! Super clean, all we needed "
United States
Kathy P.
$377 nightly
The price is $428
Mar 22 - Mar 23
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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

AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

10/10 Excellent
"Parking lot was a little suspect but they did have a big snowstorm earlier in week "
Robert E 1-night trip
Posted 7 hours ago
AmericInn by Wyndham 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. Some other homes for rent in Sheboygan include NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area and REMODELED HOME ON LAKE MICHIGAN.

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 Kohler Park Dunes State Natural Area, 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.