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Our top choices for Sheboygan vacation homes

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
15 Apr - 16 Apr
Gleason's Chouse

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
10 Apr - 11 Apr
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

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
13 Apr - 14 Apr
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

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)
"The place was very cozy and decorated so cute. We appreciated help with the fireplace and the hosts prompt and clear communication. "
United States
Kristi B.
The price is AED 463
AED 566 total
includes taxes & fees
16 Apr - 17 Apr
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

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 721
AED 2,117 total
includes taxes & fees
13 Apr - 14 Apr
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

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 1,000 total
includes taxes & fees
21 Apr - 22 Apr
The Esker Ridge Chalet, Pristine Elkhart Solitude

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 1,223 total
includes taxes & fees
17 Apr - 18 Apr
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

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 456
AED 780 total
includes taxes & fees
16 Apr - 17 Apr
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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, (41 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 422
AED 1,405 total
includes taxes & fees
22 Apr - 23 Apr
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (34 reviews)
"The property was very nice, clean, and comfortable! The hosts were very kind and available if you needed them. A great place to stay if youre in the area!"
United States
Tara F.
The price is AED 400
AED 938 total
includes taxes & fees
13 Apr - 14 Apr
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

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
10 Apr - 11 Apr
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is AED 444
AED 806 total
includes taxes & fees
10 Apr - 11 Apr
Sheboygan Riverside Condo

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, (26 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is AED 1,157
AED 2,218 total
includes taxes & fees
11 Apr - 12 Apr
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

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 2,259 total
includes taxes & fees
10 Apr - 11 Apr
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

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
10 Apr - 11 Apr
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan

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 2,168 total
includes taxes & fees
12 Apr - 13 Apr
The Links! - Luxury Golf Retreat with Golf Simulator

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 758
AED 1,661 total
includes taxes & fees
10 Apr - 11 Apr
Beautiful 3BR Home Near Lake MI

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 694
AED 1,580 total
includes taxes & fees
12 Apr - 13 Apr
Serene Home One Block From Lake Michigan

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 3,538 total
includes taxes & fees
10 Apr - 11 Apr
Beautiful private home hidden in the woods. Can sleep 11 guests

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.
The price is AED 1,444
AED 3,046 total
includes taxes & fees
10 Apr - 11 Apr
3 Min to Road America, outdoor deck, grill, & fire table
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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