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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Sheboygan holiday homes

Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is HK$1,560
HK$2,150 total
includes taxes & fees
9 Jun - 10 Jun
The Esker Ridge Chalet, Pristine Elkhart Solitude
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (43 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is HK$1,058
HK$1,505 total
includes taxes & fees
15 Jun - 16 Jun
Gleason's Chouse
Interior

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

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.0 out of 10, Wonderful, (6 reviews)
"Great place to stay."
United States
Melissa B.
The price is HK$846
HK$3,274 total
includes taxes & fees
17 Jun - 18 Jun
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Exterior detail

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, (174 reviews)
"Great place would go back"
United States
William
The price is HK$1,763
HK$2,811 total
includes taxes & fees
18 Jun - 19 Jun
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior detail

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, (33 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is HK$2,351
HK$3,770 total
includes taxes & fees
4 Jun - 5 Jun
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
TV

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
The price is HK$1,074
HK$3,291 total
includes taxes & fees
7 Jun - 8 Jun
Large Backyard, Walk to Hospital: Sheboygan Abode!
Smart TV

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, (15 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is HK$1,646
HK$2,749 total
includes taxes & fees
4 Jun - 5 Jun
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Fridge, microwave, oven, stovetop

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, (41 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 HK$1,176
HK$3,353 total
includes taxes & fees
22 Jun - 23 Jun
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Dining

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, (7 reviews)
"The house was spotless and very inviting! "
United States
Faith R.
The price is HK$1,312
HK$2,094 total
includes taxes & fees
8 Jun - 9 Jun
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Dining

Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan

Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Sheboygan
7.8 out of 10, Good, (7 reviews)
"great location walkable to downtown and Lake Michigan. Very centrally located."
United States
Laura A.
The price is HK$1,270
HK$3,096 total
includes taxes & fees
4 Jun - 5 Jun
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Shower, hair dryer, bidet, towels

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
10.0 out of 10, Exceptional, (4 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 HK$2,821
HK$4,820 total
includes taxes & fees
5 Jun - 6 Jun
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Fridge, microwave, oven, stovetop

The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (8 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 price is HK$1,873
HK$4,972 total
includes taxes & fees
23 Jun - 24 Jun
The Links! - Luxury Golf Retreat with Golf Simulator
TV, DVD player

Serene Home One Block From Lake Michigan

Serene Home One Block From Lake Michigan
Ellis Historical District
10.0 out of 10, Exceptional, (6 reviews)
"This is in the heart of downtown right near the lake. This was a clean and comfortable stay."
United States
Ra H.
The price is HK$1,625
HK$3,561 total
includes taxes & fees
4 Jun - 5 Jun
Serene Home One Block From Lake Michigan
Dining

Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Very family friendly . Great bike trails"
United States
Thomas D.
The price is HK$1,913
HK$3,933 total
includes taxes & fees
9 Jun - 10 Jun
Beautiful 3BR Home Near Lake MI
Interior

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is HK$1,387
HK$2,238 total
includes taxes & fees
4 Jun - 5 Jun
Sheboygan Riverside Condo
Outdoor dining

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room

Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room
Oostburg
9.6 out of 10, Exceptional, (229 reviews)
"Jason was incredible welcoming, the house was perfect! "
United States
Vincent P.
The price is HK$4,702
HK$7,086 total
includes taxes & fees
15 Jun - 16 Jun
Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room
Interior

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, (11 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 HK$2,109
HK$5,235 total
includes taxes & fees
9 Jun - 10 Jun
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Property grounds

Juniper & Oak LAKE HOUSE w/ Sunset Views over Kettle Moraine Lake

Juniper & Oak LAKE HOUSE w/ Sunset Views over Kettle Moraine Lake
Campbellsport
10.0 out of 10, Exceptional, (11 reviews)
"This is our second year staying at Juniper and Oak Lake House. Its the perfect vibe for a large group with lots to do on property and nearby. Shannon is a wonderful host and has thought of so many extra touches that make your stay so cozy. This year we rented the big house and the cabin in the back which is also gorgeous! Hope to be back 2026!"
Singapore
Lea D.
The price is HK$3,519
HK$6,937 total
includes taxes & fees
24 Jun - 25 Jun
Juniper & Oak LAKE HOUSE w/ Sunset Views over Kettle Moraine Lake
Outdoor dining

3 Min to Road America, outdoor deck, grill, & fire table

3 Min to Road America, outdoor deck, grill, & fire table
Plymouth
10.0 out of 10, Exceptional, (1 review)
"This place was perfect for our group. We were karting at Road America, and location was a little over a mile from the gate. Newly renovated and very nice. Hosts did lots of little things to add value to our stay. Plenty to do nearby. Kids loved the basement and yard, adults hung out on patio. Would definitely stay here again. "
United States
Matt W.
The price is HK$3,056
HK$6,474 total
includes taxes & fees
8 Jun - 9 Jun
3 Min to Road America, outdoor deck, grill, & fire table
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

6/10 Okay
"We stayed 2 nights for the Road America Motorcycle racing event. We stayed here last year as well. There was a boys soccer tournament that weekend also and there was a group that stayed at the hotel as well and very frustrating that they were not respectful to other guest and the hotel staff did nothing about them or the parents. They were running in the halls, screaming, knocking on all the doors. The breakfast area was hard to use and food was gone by 7:30 am. The hotel did have new carpet. So it was clean in that respect."
Amanda 2-night trip
Posted 10 hours ago
AmericInn by Wyndham Sheboygan

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
633
Accommodation
253 Vacation Homes
Lowest Price
HK$1,505
Highest Price
HK$7,086

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