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Holiday Homes in Sheboygan

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sheboygan holiday homes

A living room with a fireplace, a large clock, and a dining area with wooden furniture.

1. 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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is NZ$305
includes taxes & fees
7 Oct - 8 Oct
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. 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 NZ$745
includes taxes & fees
14 Oct - 15 Oct
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A dining table with a vase of green leaves and a candle.

3. 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)
"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "
United States
Christine P.
The price is NZ$423
includes taxes & fees
6 Oct - 7 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A dining area with a table, chairs, and a window with curtains.

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
The price is NZ$455
includes taxes & fees
30 Sept - 1 Oct
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
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 NZ$549
includes taxes & fees
30 Sept - 1 Oct
Sheboygan Riverside Condo
A living room with a sofa, coffee table, and TV.

6. 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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is NZ$1,054
includes taxes & fees
30 Sept - 1 Oct
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.

7. 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, (1 review)
"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"
United States
Erin S.
The price is NZ$591
includes taxes & fees
12 Oct - 13 Oct
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
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 NZ$308
includes taxes & fees
30 Sept - 1 Oct
Victorian Inn #241 | 2 Queen Beds
A cabin with a deck, a covered porch, and a paved driveway.

9. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (70 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$477
includes taxes & fees
7 Oct - 8 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The Links! - Luxury Golf Retreat with Golf Simulator
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.

11. 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.
The price is NZ$1,659
includes taxes & fees
12 Oct - 13 Oct
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

12. 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 NZ$335
includes taxes & fees
7 Oct - 8 Oct
Gleason's Chouse
A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

13. 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 NZ$578
includes taxes & fees
11 Oct - 12 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
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 to stay."
United States
Melissa B.
The price is NZ$988
includes taxes & fees
1 Oct - 2 Oct
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A large house with a well-manicured lawn and a driveway leading to the entrance.

15. Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.2 out of 10, Wonderful, (29 reviews)
"This place is my spring spiritual reset. We’ll equipped, comfortable and serene. I had a lovely stay and hope to return next year"
United States
Kristine D.
The price is NZ$1,325
includes taxes & fees
30 Sept - 1 Oct
Lake Michigan Beachfront - King Suite - Game Room
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

16. 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, (17 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is NZ$1,031
includes taxes & fees
27 Oct - 28 Oct
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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 NZ$832
includes taxes & fees
4 Oct - 5 Oct
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A patio with a fire pit, outdoor seating, and string lights.

18. 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 NZ$1,530
includes taxes & fees
29 Oct - 30 Oct
3 Min to Road America, "Amazing Location!!"
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 NZ$914
includes taxes & fees
23 Oct - 24 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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

10/10 Excellent
"The parking lot was resurfaced without notification so parking was difficult. Some had damage to their vehicles. This property seems to still be undergoing renovation. Staff is the shining star of this place!"
Troy 3-night trip
Posted 15 hours ago
AmericInn by Wyndham Sheboygan

Find out more about Sheboygan

Sheboygan Holiday Homes information

Number of reviews
581
Accommodation
258 Holiday Homes
Lowest Price
NZ$305
Highest Price
NZ$1,659

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