Aerial view of Deland Park (North Beach) and residential area in Sheboygan WI

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Sheboygan holiday homes

Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (44 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is HK$1,058
HK$1,513 total
includes taxes & fees
23 Jun - 24 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$1,073
HK$3,567 total
includes taxes & fees
8 Jul - 9 Jul
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
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)
The price is HK$1,559
HK$2,133 total
includes taxes & fees
24 Jun - 25 Jun
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, (175 reviews)
"Great place would go back"
United States
William
The price is HK$1,587
HK$2,625 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$1,074
HK$3,274 total
includes taxes & fees
21 Jun - 22 Jun
Large Backyard, Walk to Hospital: Sheboygan Abode!
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)
"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$1,058
HK$3,202 total
includes taxes & fees
22 Jun - 23 Jun
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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$3,778 total
includes taxes & fees
20 Jun - 21 Jun
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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, (16 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is HK$2,029
HK$3,246 total
includes taxes & fees
30 Jun - 1 Jul
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
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$1,857
HK$4,954 total
includes taxes & fees
22 Jun - 23 Jun
The Links! - Luxury Golf Retreat with Golf Simulator
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$1,142
HK$1,857 total
includes taxes & fees
22 Jun - 23 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$1,202
HK$3,010 total
includes taxes & fees
22 Jun - 23 Jun
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
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$2,532
HK$5,698 total
includes taxes & fees
1 Jul - 2 Jul
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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$4,819 total
includes taxes & fees
21 Jun - 22 Jun
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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$1,667
HK$3,609 total
includes taxes & fees
22 Jun - 23 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$1,871
HK$3,876 total
includes taxes & fees
22 Jun - 23 Jun
Beautiful 3BR Home Near Lake MI
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, (12 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$3,611
HK$7,041 total
includes taxes & fees
24 Jun - 25 Jun
Juniper & Oak LAKE HOUSE w/ Sunset Views over Kettle Moraine Lake
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 HK$3,989
HK$6,449 total
includes taxes & fees
30 Jun - 1 Jul
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Terrace/patio

Immersed in Nature, Hot Tub, Sleeps 9, EV Charger

Immersed in Nature, Hot Tub, Sleeps 9, EV Charger
Cascade
10.0 out of 10, Exceptional, (37 reviews)
"This house is so amazing! Full of cozy little touches that made our weekend so much fun. The beds are very comfortable, the house is fully stocked and the sauna/hot tub is the cherry on top."
United States
Cacia S.
The price is HK$3,784
HK$6,199 total
includes taxes & fees
23 Jun - 24 Jun
Immersed in Nature, Hot Tub, Sleeps 9, EV Charger
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, (15 reviews)
"Very clean and private property! "
United States
sherine m.
The price is HK$6,268
HK$7,556 total
includes taxes & fees
22 Jun - 23 Jun
Beautiful private home hidden in the woods. Can sleep 11 guests
Interior

Walk to Beaches + Restaurants: Elkhart Lake Escape

Walk to Beaches + Restaurants: Elkhart Lake Escape
Elkhart Lake
10.0 out of 10, Exceptional, (1 review)
"Beatiful place. Great neighborhood to walk in and excellent communication around our stay. "
Canada
Jacques P.
Walk to Beaches + Restaurants: Elkhart Lake Escape
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

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Big rooms, nice staff, good breakfast"
ANDREW 2-night trip
Posted 8 hours ago
Watershed Hotel

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
572
Accommodation
303 Vacation Homes
Lowest Price
HK$1,513
Highest Price
HK$7,556

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