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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sheboygan holiday homes

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
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

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, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
The price is NZ$262
includes taxes & fees
18 Nov - 19 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

3. 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, (43 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is NZ$710
includes taxes & fees
14 Dec - 15 Dec
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
United States
Tonja K.
The price is NZ$414
includes taxes & fees
14 Dec - 15 Dec
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

5. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is NZ$310
includes taxes & fees
25 Nov - 26 Nov
Victorian Inn #241 | 2 Queen Beds

6. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (73 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 NZ$537
includes taxes & fees
17 Nov - 18 Nov
The Esker Ridge Chalet, Pristine Elkhart Solitude

7. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 reviews)
"Property was clean and the check in process was smooth. Right on the beach which was fantastic!"
United States
Sherrill S.
The price is NZ$1,090
includes taxes & fees
14 Nov - 15 Nov
Beachfront Paradise: King Suite - Sleeps 8!

8. 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 NZ$581
includes taxes & fees
14 Dec - 15 Dec
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is NZ$1,053
includes taxes & fees
14 Dec - 15 Dec
The Links! - Luxury Golf Retreat with Golf Simulator

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)
"Nice location and spacious."
United States
Maggie A.
The price is NZ$987
includes taxes & fees
20 Nov - 21 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

11. 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, (50 reviews)
"So delightful and a wonderful stay!"
United States
Tom & Jenny S.
The price is NZ$433
includes taxes & fees
19 Nov - 20 Nov
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

12. 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, (19 reviews)
"Everything was amazing and if we come back next year we will be staying again"
United States
Cristy
The price is NZ$992
includes taxes & fees
14 Nov - 15 Nov
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

13. 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, (18 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is NZ$1,800
includes taxes & fees
14 Dec - 15 Dec
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

14. Private Oasis•Point Beach State Park•Lake Michigan

Private Oasis•Point Beach State Park•Lake Michigan
Two Rivers
The price is NZ$486
includes taxes & fees
16 Nov - 17 Nov
Private Oasis•Point Beach State Park•Lake Michigan

15. 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, (15 reviews)
"Great place for book club"
United States
Kelly S.
The price is NZ$980
includes taxes & fees
16 Nov - 17 Nov
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

16. Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is NZ$659
includes taxes & fees
8 Dec - 9 Dec
Road America, Elkhart Lake!

17. The Pines-Hike, Hunt, Hot tub Sleeps 9

The Pines-Hike, Hunt, Hot tub Sleeps 9
Cascade
10.0 out of 10, Exceptional, (39 reviews)
"Great place for a lot of people to stay! Host was great! Hot tub was awesome. Very comfortable beds!! Will definitely be back."
United States
Luke L.
The price is NZ$1,011
includes taxes & fees
18 Nov - 19 Nov
The Pines-Hike, Hunt, Hot tub Sleeps 9

18. 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
9.0 out of 10, Wonderful, (7 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 NZ$849
includes taxes & fees
24 Nov - 25 Nov
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

19. 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 NZ$788
includes taxes & fees
16 Nov - 17 Nov
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

20. 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, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is NZ$649
includes taxes & fees
29 Nov - 30 Nov
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sheboygan Hotel Reviews

Find out more about Sheboygan

Sheboygan Holiday Homes information

Number of reviews
596
Accommodation
252 Holiday Homes
Lowest Price
NZ$262
Highest Price
NZ$1,800

Explore a world of travel with Expedia