Sheboygan Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Sheboygan vacation rentals

Lobby

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1,023 reviews)
"Room was very clean and perfect for a downtown stay"
United States
Jim
The price is ￥23,689
￥26,887 total
includes taxes & fees
Mar 9 - Mar 10
Grandstay Residential Suites Hotel - Sheboygan
Cabin, Lake View | Beach

Cabin in Campbellsport

Tiki Beach Campground
3.0 star property
The price is ￥15,596
￥16,453 total
includes taxes & fees
Mar 10 - Mar 11
Tiki Beach Campground
1 bedroom, WiFi

Apartment in Ellis Historical District

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (24 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is ￥14,966
￥20,563 total
includes taxes & fees
Mar 15 - Mar 16
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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.
The price is ￥12,761
￥25,213 total
includes taxes & fees
Mar 8 - Mar 9
Coastal 3-BR Lower Near Lake MI and Downtown 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.
The price is ￥12,465
￥25,788 total
includes taxes & fees
Mar 9 - Mar 10
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.
The price is ￥13,490
￥37,518 total
includes taxes & fees
Mar 9 - Mar 10
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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.
The price is ￥14,179
￥26,822 total
includes taxes & fees
Mar 10 - Mar 11
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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, (123 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.
The price is ￥18,432
￥22,771 total
includes taxes & fees
Mar 9 - Mar 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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.
The price is ￥18,117
￥24,140 total
includes taxes & fees
Mar 9 - Mar 10
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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.
The price is ￥12,780
￥25,251 total
includes taxes & fees
Mar 8 - Mar 9
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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.
The price is ￥20,559
￥35,673 total
includes taxes & fees
Mar 8 - Mar 9
2nd floor loft near the lake!
Dining

Vacation Home in Sheboygan

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is ￥15,313
￥28,110 total
includes taxes & fees
Mar 8 - Mar 9
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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.
The price is ￥17,103
￥52,671 total
includes taxes & fees
Mar 8 - Mar 9
Newly Updated! Downtown & Shore
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.
Gleason's Chouse
House (4 Bedrooms) | Interior

Cottage in Campbellsport

Near Hiking: Lakefront Getaway in Campbellsport!
3.0 star property
The price is ￥20,165
￥71,356 total
includes taxes & fees
Mar 13 - Mar 14
Near Hiking: Lakefront Getaway in Campbellsport!
TV

Apartment in Sheboygan

The Beach town bungalow
The Beach town bungalow
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.
The price is ￥19,984
￥62,375 total
includes taxes & fees
Mar 10 - Mar 11
*NEW* Sleeps 8 & Spacious!
Interior

Vacation Home in Sheboygan

Sheboygan Riverside Condo
The price is ￥19,220
￥34,719 total
includes taxes & fees
Mar 8 - Mar 9
Sheboygan Riverside Condo
Bar (on property)

Villa in Elkhart Lake

The Vintage Elkhart Lake Room First Floor
The price is ￥36,297
￥61,414 total
includes taxes & fees
Mar 8 - Mar 9
The Vintage Elkhart Lake Room First Floor
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
Victorian Inn Elkhart Lake Wisconsin
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

Holiday Inn Express Sheboygan-Kohler by IHG

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent
"It was great"
Anthony 2-night trip
Posted 2 days ago
Holiday Inn Express Sheboygan-Kohler by IHG

Find out more about Sheboygan

Search for holiday rentals in Sheboygan on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheboygan using one of the methods below:

  • View our selection of featured holiday rentals in Sheboygan
  • Use the map to find apartments and other holiday homes in the Sheboygan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheboygan while they last

Look no further and take a look at our great range of rental properties in Sheboygan!

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.