Sheboygan, WI USA - September 30, 2022: Aerial view of the Sheboygan marina and surrounding area

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Sheboygan vacation homes

Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (45 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is AED 496
AED 709 total
includes taxes & fees
7 Jul - 8 Jul
Gleason's Chouse
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 AED 1,102
AED 1,771 total
includes taxes & fees
6 Jul - 7 Jul
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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, (175 reviews)
"Great place would go back"
United States
William
The price is AED 744
AED 1,230 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (60 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 AED 731
AED 1,008 total
includes taxes & fees
4 Aug - 5 Aug
The Esker Ridge Chalet, Pristine Elkhart Solitude
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 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 AED 1,014
AED 1,505 total
includes taxes & fees
27 Jul - 28 Jul
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
TV

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, the area is safe and close to the Marina. Owner/host was excellent to communicate with."
United States
Mary A.
The price is AED 503
AED 1,547 total
includes taxes & fees
6 Jul - 7 Jul
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, (17 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is AED 657
AED 1,138 total
includes taxes & fees
6 Jul - 7 Jul
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
TV, fireplace

Sunset Vista- cozy two bedroom retreat

Sunset Vista- cozy two bedroom retreat
Sheboygan
Sunset Vista- cozy two bedroom retreat
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, (12 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 AED 926
AED 2,379 total
includes taxes & fees
7 Jul - 8 Jul
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
TV, DVD player

Serene Home One Block From Lake Michigan

Serene Home One Block From Lake Michigan
Ellis Historical District
9.8 out of 10, Exceptional, (7 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 AED 928
AED 1,871 total
includes taxes & fees
7 Jul - 8 Jul
Serene Home One Block From Lake Michigan
Property grounds

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, (41 reviews)
"Nice place for 2 couples for a weekend getaway."
United States
Kimberly K.
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Interior

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

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.2 out of 10, Wonderful, (7 reviews)
"Great place to stay."
United States
Melissa B.
The price is AED 503
AED 1,676 total
includes taxes & fees
6 Jul - 7 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Terrace/patio

Beautiful private home hidden in the woods. Can sleep 11 guests

Beautiful private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (18 reviews)
"Very clean and private property! "
United States
sherine m.
The price is AED 2,938
AED 3,538 total
includes taxes & fees
6 Jul - 7 Jul
Beautiful private home hidden in the woods. Can sleep 11 guests
Exterior

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 AED 1,087
AED 2,076 total
includes taxes & fees
7 Jul - 8 Jul
Beautiful 3BR Home Near Lake MI
Property grounds

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Two Rivers
9.8 out of 10, Exceptional, (155 reviews)
"We had such a wonderful time for our second time at this property! The host had super lovely holiday touches that made our stay even more fun!"
United States
Sara B.
The price is AED 1,980
AED 3,164 total
includes taxes & fees
16 Jul - 17 Jul
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Exterior

Wyatt's Country Home - King Bed!

Wyatt's Country Home - King Bed!
Plymouth
10.0 out of 10, Exceptional, (18 reviews)
"Great,clean place"
United States
darrell J.
The price is AED 735
AED 1,194 total
includes taxes & fees
20 Jul - 21 Jul
Wyatt's Country Home - King Bed!
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, (42 reviews)
"Really nice place, everything was perfect! The shower downstairs doesn’t get very hot, but the one upstairs makes up for it. Great location and neighborhood. The garage was a huge help since it dumped 6” of snow while we were there (the owners offering to shovel). The fireplace was really awesome, and my teenage daughter really enjoyed having the entire upstairs to herself. Overall, very happy with our stay."
United States
Kevin K.
The price is AED 588
AED 1,613 total
includes taxes & fees
7 Jul - 8 Jul
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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 AED 647
AED 1,509 total
includes taxes & fees
7 Jul - 8 Jul
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Exterior

3 Mi to Road America: Spacious Elkhart Lake Home!

3 Mi to Road America: Spacious Elkhart Lake Home!
Elkhart Lake
10.0 out of 10, Exceptional, (10 reviews)
"Great place and location! "
United States
Sam B.
The price is AED 951
AED 3,009 total
includes taxes & fees
6 Jul - 7 Jul
3 Mi to Road America: Spacious Elkhart Lake Home!
Interior

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 AED 1,322
AED 2,259 total
includes taxes & fees
10 Jul - 11 Jul
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

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

8/10 Good
"This hotel is on well water so it smells and tastes funky and irony. I recommend buying some water for drinking from the nearby kwikTrip gas station. Room smelled like feet when we first walked in. I think it might have been the HVAC unit. Maybe a dirty filter or something. Otherwise it was a good stay. Beds are comfortable. Breakfast is yummy. Pool was good. Hot tub was nice. Price is reasonable"
Rami 2-night trip
Posted less than an hour ago
Comfort Inn & Suites Sheboygan I-43

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