Holiday Homes in Sheboygan

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Check prices for these dates

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

Our top choices for Sheboygan holiday homes

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 AU$267
includes taxes & fees
15 June - 16 June
Gleason's Chouse
Living area

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
9.4 out of 10, Exceptional, (13 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is AU$216
includes taxes & fees
7 June - 8 June
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Children’s area

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, (131 reviews)
"Nice getaway from the city with friendly and helpful hosts. We enjoyed a cold February weekend by the fire, with great dining in nearby Sheboygan. The proximity to the lake would be perfect in warmer weather. Highly recommend!"
United States
Kristin K.
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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 AU$385
includes taxes & fees
3 June - 4 June
The Esker Ridge Chalet, Pristine Elkhart Solitude
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 AU$467
includes taxes & fees
9 June - 10 June
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
TV

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
The price is AU$576
includes taxes & fees
3 June - 4 June
Large Backyard, Walk to Hospital: Sheboygan Abode!
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 AU$318
includes taxes & fees
3 June - 4 June
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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 AU$571
includes taxes & fees
15 June - 16 June
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
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 AU$668
includes taxes & fees
3 June - 4 June
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Smart TV

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
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 AU$504
includes taxes & fees
30 June - 1 July
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
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 AU$535
includes taxes & fees
3 June - 4 June
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
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 AU$585
includes taxes & fees
22 June - 23 June
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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 AU$837
includes taxes & fees
15 June - 16 June
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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 AU$413
includes taxes & fees
3 June - 4 June
Sheboygan Riverside Condo
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 AU$664
includes taxes & fees
3 June - 4 June
Beautiful 3BR Home Near Lake MI
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 AU$957
includes taxes & fees
23 June - 24 June
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 AU$636
includes taxes & fees
4 June - 5 June
Serene Home One Block From Lake Michigan
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 AU$1,370
includes taxes & fees
21 June - 22 June
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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)
"Nice set up and plenty of space for our ladies weekend!"
United States
Diane A.
Large Unique & Artistic Lake Michigan Beachfront House with Awesome Game Room
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 AU$1,197
includes taxes & fees
24 June - 25 June
Juniper & Oak LAKE HOUSE w/ Sunset Views over Kettle Moraine Lake
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

Super 8 by Wyndham Sheboygan WI

Super 8 by Wyndham Sheboygan WI

6/10 Okay
"Rooms served the purpose for getting a good night of rest."
Sarah 1-night trip
Posted 5 hours ago
Super 8 by Wyndham Sheboygan WI

Find out more about Sheboygan

Sheboygan Holiday Homes information

Number of reviews
776
Accommodation
253 Holiday Homes
Lowest Price
AU$216
Highest Price
AU$1,370