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Sheboygan Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Sheboygan

Lobby
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1001)
"Would definitely stay here again!"
United States
Donna
The price is HK$941
HK$1,068 total
includes taxes & fees
16 Nov - 17 Nov
Grandstay Residential Suites Hotel - Sheboygan
Living area
2nd floor loft near the lake!

2nd floor loft near the lake!

Manitowoc
9.8 out of 10, Exceptional, (15)
"My family and I had a great stay at this property. Quiet neighbors and plenty of parking available. Host was prompt to reply to our questions. Also, thank you for the chocolates! Looking forward to booking this property in the future."
United States
Victor F.
The price is HK$1,014
HK$1,751 total
includes taxes & fees
17 Nov - 18 Nov
2nd floor loft near the lake!
Exterior
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, (116)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
United States
Shelby L.
The price is HK$1,010
HK$1,230 total
includes taxes & fees
1 Dec - 2 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Fridge, microwave, oven, stovetop
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, (23)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
The price is HK$738
HK$1,014 total
includes taxes & fees
19 Nov - 20 Nov
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Interior
Gleason's Chouse

Gleason's Chouse

Campbellsport
10.0 out of 10, Exceptional, (41)
"So interesting and comfy atmosphere. We loved all the attention to detail. Great amneties. Definitely going back!"
United States
Jenee S.
The price is HK$1,088
HK$1,550 total
includes taxes & fees
22 Nov - 23 Nov
Gleason's Chouse
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)
"We loved the location because it was easy to walk everywhere. We had every amenity that we needed. Also the off-site manager Jeff was very responsive. "
United States
Karen G.
The price is HK$1,119
HK$2,134 total
includes taxes & fees
16 Nov - 17 Nov
First Floor Pet Friendly Queen Suite with Single Pull-out
Interior
Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!

3.0 star property
Sheboygan
The price is HK$1,577
HK$3,288 total
includes taxes & fees
16 Nov - 17 Nov
Large Backyard, Walk to Hospital: Sheboygan Abode!
3 bedrooms, iron/ironing board, WiFi, bed sheets
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, (3)
"Needed somewhere clean, safe and affordable to bring our family for a few days worth of a family wedding. This home was perfect for us. The space was clean and welcoming. Communication was easy. Close to everything we needed plus some. "
United States
Patricia O.
The price is HK$886
HK$1,535 total
includes taxes & fees
16 Nov - 17 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Sheboygan
9.2 out of 10, Wonderful, (10)
"The property was spotless - extremely clean and I appreciated that very much. I had to search to find the bathroom and the vanity was so small it did not allow ease to get ready. I was looking for a book about the property and how the host preferred you leave it (example: bedding removed, etc.) So I had to guess. I slept in the one room one night but the bed was too soft so I switched rooms and slept in the other bed which was much better. "
United States
Kristine
The price is HK$797
HK$1,434 total
includes taxes & fees
18 Nov - 19 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Indoor pool, a heated pool
Upscale Waterfront and Pool View Condo!!

Upscale Waterfront and Pool View Condo!!

Elkhart Lake
10.0 out of 10, Exceptional, (4)
"We enjoyed the nearby amenities for water activities. The unit was clean and welcoming. Instructions for stay were clear. We very much appreciated our time here."
United States
Lauren B.
The price is HK$1,455
HK$3,222 total
includes taxes & fees
17 Nov - 18 Nov
Upscale Waterfront and Pool View Condo!!
Exterior
Charming studio apartment - Perfect location for the outdoor explorer

Charming studio apartment - Perfect location for the outdoor explorer

Kewaskum
9.8 out of 10, Exceptional, (8)
"Well kept property. Friendly owners,"
United States
James K.
The price is HK$1,161
HK$2,371 total
includes taxes & fees
16 Nov - 17 Nov
Charming studio apartment - Perfect location for the outdoor explorer
Interior
Newly Updated! Downtown & Shore

Newly Updated! Downtown & Shore

Sheboygan
9.6 out of 10, Exceptional, (4)
"Clean, spacious, and quiet. "
United States
Thomas S.
The price is HK$845
HK$2,599 total
includes taxes & fees
16 Nov - 17 Nov
Newly Updated! Downtown & Shore
Property grounds
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, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is HK$797
HK$1,434 total
includes taxes & fees
16 Nov - 17 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Fridge, oven, stovetop, dishwasher
Surfside Retreat – Walk to Lake

Surfside Retreat – Walk to Lake

Ellis Historical District
The price is HK$614
HK$1,818 total
includes taxes & fees
17 Nov - 18 Nov
Surfside Retreat – Walk to Lake
Smart TV, books
*NEW* Sleeps 8 & Spacious!

*NEW* Sleeps 8 & Spacious!

Sheboygan
10.0 out of 10, Exceptional, (27)
"Very clean and very comfortable beds"
United States
douglas c.
The price is HK$916
HK$2,989 total
includes taxes & fees
16 Nov - 17 Nov
*NEW* Sleeps 8 & Spacious!
Fridge, microwave, oven, stovetop
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

Two Rivers
9.8 out of 10, Exceptional, (37)
"Loved it. Cute place, good parking, close to everything."
United States
Bernardine B.
The price is HK$1,197
HK$1,535 total
includes taxes & fees
1 Dec - 2 Dec
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Indoor pool, a heated pool
Modern Room Near Indoor Pool

Modern Room Near Indoor Pool

Elkhart Lake
9.6 out of 10, Exceptional, (4)
"Center located and great access to pools beach etc….dog also had a blast!"
United States
John M.
The price is HK$1,119
HK$2,134 total
includes taxes & fees
16 Nov - 17 Nov
Modern Room Near Indoor Pool
Fridge, microwave, oven, stovetop
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan
10.0 out of 10, Exceptional, (4)
"The house is very comfortable inside and outside. It has an enclosed back yard for grilling and chilling. The beds are comfortable. The kitchen is equipped for any meal you want to create. The host is very helpful and responded quickly to any questions I had. I will use this home again!"
United States
Pete J.
The price is HK$832
HK$1,474 total
includes taxes & fees
16 Nov - 17 Nov
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Private kitchen
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.

2.0 star property
Ellis Historical District
9.6 out of 10, Exceptional, (12)
"Place was clean, up to date, easy to access. The place was well stocked with cooking utensils, plates, silverware, etc. The place was very comfortable. Would rebook the next time we are in Sheboygan"
United States
Jay R.
The price is HK$894
HK$1,191 total
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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, (31)
"We came just to relax and have fun. We enjoyed sitting out on the patio with our dog and books and having a bonfire in the fire pit. The home is very well labeled and cozy—we loved it! "
United States
Jeremy E.
The price is HK$847
HK$1,985 total
includes taxes & fees
26 Nov - 27 Nov
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

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent
"Yes- everything was in great order and well kept. Breakfast was outstanding."
Kathleen M 1-night trip
Posted 3 days ago
La Quinta Inn 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:

  • 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!

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, 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?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: This highly rated holiday home rental in Sheboygan is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travellers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 96 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 Kohler Park Dunes State Natural Area, or simply take in cultural attractions like John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. While here, Blue Harbor Resort & Conference Center Water Park and Sheboygan South Pier 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.