A red lighthouse amidst rough seas with waves crashing against a pier.

Holiday Homes in Sheboygan

  • 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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Sheboygan holiday homes

A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

1. 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, (20 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is AU$393
includes taxes & fees
31 Oct - 1 Nov
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

2. 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, (149 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is AU$246
includes taxes & fees
9 Nov - 10 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A dining area with a table, chairs, and a window with curtains.

3. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A dining table with a vase of green leaves and a candle.

4. 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, (8 reviews)
"We stayed a very short time due to many wedding details and festivities and the stay was just what we needed. Convenient to wedding location, very clean, comfy beds, friendly and reliable host! Would highly recommend!"
United States
Stephanie M.
The price is AU$297
includes taxes & fees
21 Oct - 22 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

5. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is AU$373
includes taxes & fees
20 Oct - 21 Oct
Sheboygan Riverside Condo
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

6. 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)
"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"
United States
Anonymous traveller
The price is AU$548
includes taxes & fees
16 Nov - 17 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A cabin with a deck, a covered porch, and a paved driveway.

7. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (71 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is AU$388
includes taxes & fees
20 Oct - 21 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
A hotel room with two beds, a dining area, and a view of the outdoors.

8. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AU$254
includes taxes & fees
20 Oct - 21 Oct
Victorian Inn #241 | 2 Queen Beds
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

9. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (15 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is AU$860
includes taxes & fees
20 Oct - 21 Oct
The Links! - Luxury Golf Retreat with Golf Simulator
A living room with a sofa, coffee table, and TV.

10. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
9.8 out of 10, Exceptional, (43 reviews)
"This nice big house has a great location for visiting Sheboygan and Lake Michigan. It was easy to walk to excellent restaurants and vintage stores. We also caught the Wednesday farmers market and saw the pops band concert that night. The house is well air-conditioned and comfortable. Great stay!"
United States
Nikki M.
The price is AU$913
includes taxes & fees
17 Nov - 18 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

11. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place. The owners were very helpful during our stay with recommendations on things to do as our fishing trip was cancelled!"
United States
Nicole B.
The price is AU$478
includes taxes & fees
20 Oct - 21 Oct
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
An outdoor seating area with a view of a lake, surrounded by trees and a barbecue grill.

12. 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, (48 reviews)
"So delightful and a wonderful stay!"
United States
Tom & Jenny S.
The price is AU$357
includes taxes & fees
20 Oct - 21 Oct
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

13. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
9.8 out of 10, Exceptional, (18 reviews)
"Everything was amazing and if we come back next year we will be staying again"
United States
Cristy
The price is AU$811
includes taxes & fees
27 Oct - 28 Oct
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
A room with a wooden ceiling, large windows, and a seating area with two chairs and a table.

14. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.6 out of 10, Exceptional, (14 reviews)
"Great place for book club"
United States
Kelly S.
The price is AU$798
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A patio with a fire pit, outdoor seating, and string lights.

15. 3 Min to Road America, "Amazing Location!!"

3 Min to Road America, "Amazing Location!!"
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Great place with tons of space and updated rooms. Conveniently located for everything we did. I would absolutely recommend this place!!"
United States
Patrick F.
The price is AU$1,225
includes taxes & fees
31 Oct - 1 Nov
3 Min to Road America, "Amazing Location!!"
A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

16. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

17. 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, (36 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is AU$667
includes taxes & fees
27 Oct - 28 Oct
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

18. 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, (181 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is AU$471
includes taxes & fees
26 Oct - 27 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
A spacious lobby with leather sofas, a chandelier, a large TV, and a foosball table.

19. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Kiel
8.8 out of 10, Excellent, (6 reviews)
"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."
United States
Ryan K.
The price is AU$706
includes taxes & fees
21 Oct - 22 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

20. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (50 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is AU$284
includes taxes & fees
22 Oct - 23 Oct
Gleason's Chouse
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"Love it here"
mitch 1-night trip
Posted less than an hour ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan

Sheboygan Holiday Homes information

Number of reviews
687
Accommodation
257 Holiday Homes
Lowest Price
AU$246
Highest Price
AU$1,225