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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, (126 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 AED 514
AED 620 total
includes taxes & fees
7 Apr - 8 Apr
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, (14 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is AED 290
AED 600 total
includes taxes & fees
30 Mar - 31 Mar
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 AED 422
AED 563 total
includes taxes & fees
25 Mar - 26 Mar
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (41 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is AED 496
AED 709 total
includes taxes & fees
7 Apr - 8 Apr
Gleason's Chouse

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 AED 441
AED 1,430 total
includes taxes & fees
25 Mar - 26 Mar
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

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 AED 704
AED 2,111 total
includes taxes & fees
25 Mar - 26 Mar
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
9.8 out of 10, Exceptional, (25 reviews)
"Great location!! Super clean, all we needed "
United States
Kathy P.
The price is AED 661
AED 1,572 total
includes taxes & fees
25 Mar - 26 Mar
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

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 AED 744
AED 1,230 total
includes taxes & fees
30 Mar - 31 Mar
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

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 1,004 total
includes taxes & fees
21 Apr - 22 Apr
The Esker Ridge Chalet, Pristine Elkhart Solitude

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 1,771 total
includes taxes & fees
25 Mar - 26 Mar
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

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 1,322
AED 2,248 total
includes taxes & fees
25 Mar - 26 Mar
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

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 476
AED 803 total
includes taxes & fees
6 Apr - 7 Apr
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
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)
"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
25 Mar - 26 Mar
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 AED 2,938
AED 3,542 total
includes taxes & fees
25 Mar - 26 Mar
Beautiful private home hidden in the woods. Can sleep 11 guests

Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.8 out of 10, Exceptional, (17 reviews)
"Great place…clean and very nice; fantastic location; great communication…recommended"
United States
Victor W.
The price is AED 1,073
AED 3,015 total
includes taxes & fees
29 Mar - 30 Mar
Lake Michigan Beachfront - King Suite - Game Room

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 2,893 total
includes taxes & fees
25 Mar - 26 Mar
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, (4 reviews)
"This is an amazing house, very clean, well appointed, and spacious. Amber is an attentive & wonderful host. We had a great time there!"
United States
Kelly A.
The price is AED 2,111
AED 4,367 total
includes taxes & fees
25 Mar - 26 Mar
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 AED 3,315
AED 4,850 total
includes taxes & fees
25 Mar - 26 Mar
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 AED 3,669
AED 5,902 total
includes taxes & fees
25 Mar - 26 Mar
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

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