A coastal town with a beach, residential areas, and a church steeple.

Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Sheboygan vacation rentals

Cabin, Lake View | Beach

Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
7.4 out of 10, Good, (3 reviews)
"Me and my brother had an incredible time here. It was exactly what we were looking for. From the staff, to the property and the room itself. The natures walls close by. It was great and will be returning with more of the family again."
United States
Jessica
The price is AED 628
AED 663 total
includes taxes & fees
27 Jul - 28 Jul
Tiki Beach Campground
Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,046 reviews)
"Will remember to stay there again."
United States
Sonia
The price is AED 693
AED 787 total
includes taxes & fees
1 Jul - 2 Jul
Grandstay Residential Suites Hotel - Sheboygan
1 bedroom, WiFi

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.6 out of 10, Exceptional, (29 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is AED 349
AED 479 total
includes taxes & fees
6 Jul - 7 Jul
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
3 bedrooms, iron/ironing board, travel crib, WiFi

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
10.0 out of 10, Exceptional, (4 reviews)
"We are moving to Sheboygan and just needed a place for the 3 of to stay while we got the lay off the land. It was a clean and surprisingly roomy place. Thanks again for the hospitality!"
United States
Woomy B.
The price is AED 555
AED 914 total
includes taxes & fees
13 Jul - 14 Jul
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Living area

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (20 reviews)
"The location was amazing and the place is really nice! Absolutely love that it is dog friendly and the host is really responsive! We will definitely be staying again! "
United States
Emily G.
The price is AED 540
AED 913 total
includes taxes & fees
12 Jul - 13 Jul
2nd floor loft near the lake!
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (60 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.
The price is AED 731
AED 1,011 total
includes taxes & fees
7 Jul - 8 Jul
The Esker Ridge Chalet, Pristine Elkhart Solitude
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (45 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is AED 496
AED 701 total
includes taxes & fees
6 Jul - 7 Jul
Gleason's Chouse
Interior

Apartment Centrally Located

Apartment Centrally Located
Plymouth
10.0 out of 10, Exceptional, (1 review)
"Very reasonable for the price. Staff was helpful and friendly. Would definitely stay again."
United States
Russ
Apartment Centrally Located
Smart TV

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is AED 621
AED 1,088 total
includes taxes & fees
1 Jul - 2 Jul
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
TV

Centrally located apartment

Centrally located apartment
Plymouth
7.6 out of 10, Good, (4 reviews)
"Place was clean and near Road America"
United States
Heather P.
The price is AED 441
AED 710 total
includes taxes & fees
1 Jul - 2 Jul
Centrally located apartment
Interior

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.2 out of 10, Wonderful, (7 reviews)
"Great place to stay."
United States
Melissa B.
The price is AED 503
AED 1,676 total
includes taxes & fees
2 Jul - 3 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Exterior detail

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (175 reviews)
"Great place would go back"
United States
William
The price is AED 744
AED 1,230 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Interior

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
3.0 star property
Two Rivers
The price is AED 665
AED 1,748 total
includes taxes & fees
2 Jul - 3 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Interior

Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
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 AED 483
AED 1,469 total
includes taxes & fees
1 Jul - 2 Jul
Sleeps 8 & Spacious!
Fridge, microwave, oven, stovetop

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (42 reviews)
"Really nice place, everything was perfect! The shower downstairs doesn’t get very hot, but the one upstairs makes up for it. Great location and neighborhood. The garage was a huge help since it dumped 6” of snow while we were there (the owners offering to shovel). The fireplace was really awesome, and my teenage daughter really enjoyed having the entire upstairs to herself. Overall, very happy with our stay."
United States
Kevin K.
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
TV

Apartment Centrally Located

Apartment Centrally Located
Plymouth
9.2 out of 10, Wonderful, (5 reviews)
"Great, reasonable priced apartment.. it was quiet and had everything I needed.. very comfortable"
United States
Diana A.
Apartment Centrally Located
Property grounds

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (41 reviews)
"Nice place for 2 couples for a weekend getaway."
United States
Kimberly K.
The price is AED 547
AED 1,138 total
includes taxes & fees
19 Jul - 20 Jul
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Dining

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is AED 613
AED 1,272 total
includes taxes & fees
21 Jul - 22 Jul
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Exterior

Country Guest House

Country Guest House
Plymouth
9.8 out of 10, Exceptional, (17 reviews)
"very nice property, just as described, would definitely stay there again"
United States
Michael
The price is AED 735
AED 1,108 total
includes taxes & fees
19 Jul - 20 Jul
Country Guest House
Iron/ironing board, WiFi, bed sheets

Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
Victorian Inn #241 | 2 Queen Beds
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

Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43

8/10 Good
"The only issue we had was getting our room to lock, having to put all your weight onto the door to latch otherwise use deadbolt, when leaving room had to pull really hard on handle to get it to latch with multiple attempts, hotel was booked so unable to change rooms. But over all room and amenities clean and decent breakfast"
Dominique 2-night trip
Posted 1 hour ago
Quality Inn Sheboygan North I-43

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?

REMODELED HOME ON LAKE MICHIGAN: This Sheboygan vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. 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 94 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.