Sheboygan Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Sheboygan holiday rentals

Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,026 reviews)
"Room was clean, staff was nice. The breakfast was pretty darn good. "
United States
andrea
The price is HK$1,097
HK$1,246 total
includes taxes & fees
5 Apr - 6 Apr
Grandstay Residential Suites Hotel - Sheboygan
Beach

Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
The price is HK$776
HK$819 total
includes taxes & fees
4 Apr - 5 Apr
Tiki Beach Campground
Smart TV

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is HK$619
HK$1,281 total
includes taxes & fees
6 Apr - 7 Apr
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
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
9.8 out of 10, Exceptional, (25 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is HK$745
HK$1,023 total
includes taxes & fees
7 Apr - 8 Apr
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Bar (on property)

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is HK$952
HK$5,026 total
includes taxes & fees
5 Apr - 6 Apr
Victorian Inn Elkhart Lake Wisconsin
Exterior

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (3 reviews)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is HK$705
HK$2,313 total
includes taxes & fees
5 Apr - 6 Apr
Logan Ave Holiday House - Upper
Children’s area

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (126 reviews)
"The place was very cozy and decorated so cute. We appreciated help with the fireplace and the hosts prompt and clear communication. "
United States
Kristi B.
The price is HK$988
HK$1,207 total
includes taxes & fees
15 Apr - 16 Apr
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Living area

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
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 HK$901
HK$1,201 total
includes taxes & fees
7 Apr - 8 Apr
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Living area

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (16 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is HK$1,023
HK$1,775 total
includes taxes & fees
4 Apr - 5 Apr
2nd floor loft near the lake!
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (41 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is HK$1,058
HK$1,513 total
includes taxes & fees
8 Apr - 9 Apr
Gleason's Chouse
Interior

*NEW* Sleeps 8 & Spacious!

*NEW* 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 HK$915
HK$2,995 total
includes taxes & fees
6 Apr - 7 Apr
*NEW* Sleeps 8 & Spacious!
Interior

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
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 HK$893
HK$1,557 total
includes taxes & fees
9 Apr - 10 Apr
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Front of property

Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
The price is HK$1,262
HK$3,063 total
includes taxes & fees
6 Apr - 7 Apr
Modern South Pier Condo on Sheboygan River!
Fridge, microwave, oven, stovetop

Luxury Suites #5

Luxury Suites #5
Brillion
The price is HK$1,481
HK$2,334 total
includes taxes & fees
7 Apr - 8 Apr
Luxury Suites #5
Smart TV, books

*NEW* Beautiful & Convenient!

*NEW* Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (20 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is HK$870
HK$2,643 total
includes taxes & fees
6 Apr - 7 Apr
*NEW* Beautiful & Convenient!
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, (12 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is HK$745
HK$1,913 total
includes taxes & fees
4 May - 5 May
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Exterior detail

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (32 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is HK$2,351
HK$3,779 total
includes taxes & fees
5 Apr - 6 Apr
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Bar (on property)

First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out
Elkhart Lake
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.
The price is HK$1,806
HK$3,038 total
includes taxes & fees
16 Apr - 17 Apr
First Floor Pet Friendly Queen Suite with Single Pull-out
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, (174 reviews)
"Great place would go back"
United States
William
The price is HK$1,587
HK$2,617 total
includes taxes & fees
11 Apr - 12 Apr
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
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, (34 reviews)
"The property was very nice, clean, and comfortable! The hosts were very kind and available if you needed them. A great place to stay if youre in the area!"
United States
Tara F.
The price is HK$854
HK$2,002 total
includes taxes & fees
19 Apr - 20 Apr
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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

4/10 Poor
"Breakfast was good, parking ok. Under construction, difficult to breathe, chemicals in the air, burning. Water ph levels very high, recommend to stay away until construction is done. Staff has been pretty good for the most part. Only so much they can do. Workers messy, lots of mold, just covering it up. Room ok hard to breathe. Turn on fans, chemicals fly. "
KARI 7-night trip
Posted 2 days ago
AmericInn by Wyndham Sheboygan

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:

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

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to John Michael Kohler Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Sheboygan speak positively about the popular beaches 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 holiday rentals that Sheboygan has to offer?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This highly rated holiday home rental in Sheboygan 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 holiday with amenities such as a selection of games. Our travellers also rate REMODELED HOME ON LAKE MICHIGAN as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 98 Expedia holiday rentals in Sheboygan for a memorable holiday.

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 holiday rental in Sheboygan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheboygan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.