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Check prices for these dates

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

Our top choices for Sheboygan vacation 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
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.
The price is ￥23,742
￥42,937 total
includes taxes & fees
Oct 31 - Nov 1
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A door with a numeric keypad lock.

2. 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 ￥18,202
￥35,032 total
includes taxes & fees
Nov 17 - Nov 18
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

3. 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 ￥22,159
￥26,717 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A dining area with a wooden table, two chairs, a patterned rug, and a kitchen in the background.

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 ￥17,807
￥34,764 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥27,541
￥44,190 total
includes taxes & fees
Oct 25 - Oct 26
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 traveler
The price is ￥18,519
￥60,723 total
includes taxes & fees
Nov 16 - Nov 17
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

7. 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 ￥35,588
￥96,763 total
includes taxes & fees
Nov 3 - Nov 4
The Links! - Luxury Golf Retreat with Golf Simulator
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 ￥16,122
￥28,757 total
includes taxes & fees
Oct 23 - Oct 24
Victorian Inn #241 | 2 Queen Beds
A living room with a sofa, coffee table, and TV.

9. 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 ￥49,824
￥94,790 total
includes taxes & fees
Nov 3 - Nov 4
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.

10. 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 ￥41,786
￥54,254 total
includes taxes & fees
Oct 25 - Oct 26
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.

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, (48 reviews)
"So delightful and a wonderful stay!"
United States
Tom & Jenny S.
The price is ￥15,659
￥37,521 total
includes taxes & fees
Nov 2 - Nov 3
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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.

12. 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 ￥90,631
￥168,753 total
includes taxes & fees
Nov 3 - Nov 4
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A room with a wooden ceiling, large windows, and a seating area with two chairs and a table.

13. 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 ￥21,669
￥89,402 total
includes taxes & fees
Oct 23 - Oct 24
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

14. 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 ￥31,339
￥92,177 total
includes taxes & fees
Oct 27 - Oct 28
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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 ￥68,060
￥138,265 total
includes taxes & fees
Oct 31 - Nov 1
3 Min to Road America, "Amazing Location!!"
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

16. 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 ￥47,451
￥76,260 total
includes taxes & fees
Oct 29 - Oct 30
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A kitchen with wooden cabinets, a stove, a dishwasher, and a window with a view of trees.

17. 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 ￥32,029
￥52,982 total
includes taxes & fees
Oct 29 - Oct 30
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.

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 ￥41,994
￥79,347 total
includes taxes & fees
Oct 25 - Oct 26
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.

19. 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 ￥21,368
￥31,561 total
includes taxes & fees
Oct 25 - Oct 26
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.
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Top Sheboygan Hotel Reviews

AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

10/10 Excellent
"The 2 gentleman that worked front desk, were very polite and helpful and hard working."
Rodney 3-night trip
Posted 1 day ago
AmericInn by Wyndham Sheboygan

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
618
Accommodation
258 Vacation Homes
Lowest Price
￥26,717
Highest Price
￥168,753