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Our top choices for Sheboygan vacation homes

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, (123 reviews)
"Our host was warm and welcoming and our accommodations were wonderful (well appointed and decorated … every detail well thought out)."
United States
Heidi E.
The price is ¥18,258
¥22,556 total
includes taxes & fees
Mar 4 - Mar 5
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

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)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is ¥12,328
¥25,505 total
includes taxes & fees
Mar 9 - Mar 10
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

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 ¥17,946
¥23,912 total
includes taxes & fees
Mar 3 - Mar 4
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

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 ¥31,054
¥42,311 total
includes taxes & fees
Mar 3 - Mar 4
The Esker Ridge Chalet, Pristine Elkhart Solitude

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 price is ¥18,726
¥60,752 total
includes taxes & fees
Mar 3 - Mar 4
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

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 ¥31,600
¥52,272 total
includes taxes & fees
Mar 9 - Mar 10
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

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
9.6 out of 10, Exceptional, (10 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 ¥29,915
¥89,676 total
includes taxes & fees
Mar 3 - Mar 4
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

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)
"Great location!! Super clean, all we needed "
United States
Kathy P.
The price is ¥28,089
¥66,774 total
includes taxes & fees
Mar 3 - Mar 4
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

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 ¥46,815
¥75,238 total
includes taxes & fees
Mar 3 - Mar 4
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

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 ¥13,483
¥25,930 total
includes taxes & fees
Mar 3 - Mar 4
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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 ¥56,178
¥94,994 total
includes taxes & fees
Mar 4 - Mar 5
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.8 out of 10, Exceptional, (17 reviews)
" Great location! Enjoyed the sunrises. "
United States
Barb S.
The price is ¥32,927
¥104,253 total
includes taxes & fees
Mar 3 - Mar 4
Lake Michigan Beachfront - King Suite - Game Room

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
The price is ¥18,414
¥33,943 total
includes taxes & fees
Mar 5 - Mar 6
Sheboygan Riverside Condo

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)
"If I could give it higher than 5 stars I would. Property was spotless, like new, great communication with owner, very easy check in/check out process, website doesn't do it justice. Will definitely rent again on our next trip to the area."
United States
Frank V.
The price is ¥35,111
¥96,175 total
includes taxes & fees
Mar 15 - Mar 16
The Links! - Luxury Golf Retreat with Golf Simulator

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 ¥124,840
¥150,474 total
includes taxes & fees
Mar 3 - Mar 4
Beautiful private home hidden in the woods. Can sleep 11 guests

Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is ¥27,309
¥58,455 total
includes taxes & fees
Mar 3 - Mar 4
Road America, Elkhart Lake!

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 ¥65,385
¥125,222 total
includes taxes & fees
Mar 9 - Mar 10
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.

This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Elkhart Lake
10.0 out of 10, Exceptional, (3 reviews)
"Gorgeous house with everything you need and just a block away from RA"
United States
Hiroshi W.
The price is ¥89,690
¥179,100 total
includes taxes & fees
Mar 3 - Mar 4
This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.

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 ¥140,835
¥205,215 total
includes taxes & fees
Mar 3 - Mar 4
5 min from Road America. Great yard and plenty of parking

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 ¥155,894
¥251,890 total
includes taxes & fees
Mar 3 - Mar 4
Brand new Modern, 6 bedroom waterfront home on a beautiful Long 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

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
535
Accommodation
262 Vacation Homes
Lowest Price
¥22,556
Highest Price
¥251,890