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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Sheboygan vacation homes

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, (121 reviews)
"Lovely place and quiet"
United States
grandma d.
The price is AED 430
AED 531 total
includes taxes & fees
9 Feb - 10 Feb
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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
9.6 out of 10, Exceptional, (12 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 AED 422
AED 563 total
includes taxes & fees
7 Feb - 8 Feb
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay and even better hosts’. The house is conveniently located to everything we wanted to explore and was a great place to unwind after a long day. The host was very helpful and made sure we were settled in and having a good time. Would love to come back soon! "
United States
Riley W.
The price is AED 217
AED 517 total
includes taxes & fees
9 Feb - 10 Feb
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Smart TV

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
10.0 out of 10, Exceptional, (24 reviews)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is AED 463
AED 775 total
includes taxes & fees
8 Mar - 9 Mar
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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, (40 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 Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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 AED 731
AED 996 total
includes taxes & fees
10 Feb - 11 Feb
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, (173 reviews)
"Great place would go back"
United States
William
The price is AED 826
AED 1,325 total
includes taxes & fees
8 Mar - 9 Mar
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Interior

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
Sheboygan Riverside Condo
Fridge, microwave, oven, stovetop

Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.

Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Campbellsport
The price is AED 3,669
AED 5,971 total
includes taxes & fees
8 Feb - 9 Feb
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
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, (32 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is AED 1,102
AED 1,767 total
includes taxes & fees
8 Mar - 9 Mar
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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, (14 reviews)
"Very clean and private property! "
United States
sherine m.
The price is AED 2,938
AED 3,542 total
includes taxes & fees
6 Feb - 7 Feb
Beautiful private home hidden in the woods. Can sleep 11 guests
Dining

Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is AED 643
AED 1,364 total
includes taxes & fees
8 Feb - 9 Feb
Road America, Elkhart Lake!
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, (3 reviews)
"Wonderful place! "
United States
Colleen & Mark G.
The price is AED 1,469
AED 2,414 total
includes taxes & fees
8 Mar - 9 Mar
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Terrace/patio

Spacious Property with Hot Tub, Jukebox, Sleeps 10

Spacious Property with Hot Tub, Jukebox, Sleeps 10
Cascade
10.0 out of 10, Exceptional, (34 reviews)
"This was my third time staying at this place. Pam is the ultimate host. Her place is always clean and very welcoming. She had all the necessary items to make s'mores. Her place is very family-friendly. I would highly recommend this place to anyone. My family and I are already looking forward to visiting again. "
United States
Roberta V.
Spacious Property with Hot Tub, Jukebox, Sleeps 10
Spa

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.
3 Min to Road America, outdoor deck, grill, & fire table
Fridge, microwave, oven, stovetop

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (12 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is AED 1,539
AED 2,947 total
includes taxes & fees
8 Mar - 9 Mar
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Property grounds

5 min from Road America. Great yard and plenty of parking

5 min from Road America. Great yard and plenty of parking
Elkhart Lake
10.0 out of 10, Exceptional, (2 reviews)
" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...
United States
Paul & Jacqleene M.
The price is AED 2,879
AED 4,339 total
includes taxes & fees
6 Feb - 7 Feb
5 min from Road America. Great yard and plenty of parking
TV, DVD player

Beautiful 2 Bedroom Duplex

Beautiful 2 Bedroom Duplex
Fond du Lac
9.8 out of 10, Exceptional, (16 reviews)
"Nice house and easy to find"
United States
Mary G.
The price is AED 511
AED 1,104 total
includes taxes & fees
8 Feb - 9 Feb
Beautiful 2 Bedroom Duplex
Interior

Charming 3-bedroom house with AC and WiFi in Appleton

Charming 3-bedroom house with AC and WiFi in Appleton
Appleton
9.8 out of 10, Exceptional, (6 reviews)
"Attendees at Air Adventure 2025. Clean and quiet little house to rest in after long days at the airshow. Plenty of dining options."
United States
Mark B.
Charming 3-bedroom house with AC and WiFi in Appleton
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

Holiday Inn Express Sheboygan-Kohler by IHG

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent
"The room was spotless. The bed was very comfortable and the shower was amazing."
MARGARET 1-night trip
Posted 3 days ago
Holiday Inn Express Sheboygan-Kohler by IHG

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