A coastal town with a beach, residential areas, and a church steeple.

Search Vacation Homes in Sheboygan

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Sheboygan vacation 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 AED 496
AED 709 total
includes taxes & fees
2 Jul - 3 Jul
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 AED 503
AED 1,672 total
includes taxes & fees
1 Jul - 2 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)
"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 1,004 total
includes taxes & fees
7 Jul - 8 Jul
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 AED 744
AED 1,230 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 AED 503
AED 1,534 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 AED 496
AED 1,501 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 AED 1,102
AED 1,771 total
includes taxes & fees
21 Jun - 22 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 AED 1,649
AED 2,410 total
includes taxes & fees
21 Jun - 22 Jun
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 AED 826
AED 2,264 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 AED 555
AED 897 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 AED 563
AED 1,411 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 AED 1,150
AED 2,624 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 AED 1,322
AED 2,259 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 AED 797
AED 1,714 total
includes taxes & fees
23 Jun - 24 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 AED 893
AED 1,839 total
includes taxes & fees
23 Jun - 24 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.
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 AED 1,980
AED 3,164 total
includes taxes & fees
16 Jul - 17 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 AED 1,580
AED 2,670 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 AED 2,938
AED 3,542 total
includes taxes & fees
20 Jul - 21 Jul
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.
The price is AED 3,607
AED 6,497 total
includes taxes & fees
28 Jun - 29 Jun
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheboygan Hotel Reviews

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"This is an excellent newer hotel in the older section of Sheboygan. It's in a quiet area of the downtown within walking distance of several good eating spots. The spacious lobby includes tables for the provided breakfast. Rooms were clean and comfortable. I would revisit this hotel on my next visit to Sheboygan."
Bernard 2-night trip
Posted 8 hours ago
Grandstay Residential Suites Hotel - Sheboygan

Explore a world of travel with Expedia