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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Sheboygan vacation homes

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
9.8 out of 10, Exceptional, (15 reviews)
"Welcoming and attentive hosts with helpful recommendations, clean and cozy space. "
United States
Brenda R.
The price is ￥14,850
￥28,387 total
includes taxes & fees
May 11 - May 12
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (42 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is ￥21,103
￥30,181 total
includes taxes & fees
May 10 - May 11
Gleason's Chouse
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 ￥17,977
￥23,953 total
includes taxes & fees
May 8 - May 9
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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, (129 reviews)
"Welcoming and accommodating host, very clean and cozy cottage, amazing fireplace "
United States
Cade R.
The price is ￥21,103
￥25,563 total
includes taxes & fees
May 18 - May 19
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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 ￥31,108
￥42,549 total
includes taxes & fees
May 12 - May 13
The Esker Ridge Chalet, Pristine Elkhart Solitude
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, (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 ￥39,080
￥86,583 total
includes taxes & fees
Jun 7 - Jun 8
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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, (174 reviews)
"Great place would go back"
United States
William
The price is ￥31,655
￥52,363 total
includes taxes & fees
May 18 - May 19
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
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
9.6 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 ￥36,298
￥97,500 total
includes taxes & fees
May 10 - May 11
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
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 ￥46,896
￥75,368 total
includes taxes & fees
May 10 - May 11
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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 ￥56,275
￥96,148 total
includes taxes & fees
May 10 - May 11
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Property grounds

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, (35 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.
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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
9.8 out of 10, Exceptional, (26 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥49,241
￥93,681 total
includes taxes & fees
May 8 - May 9
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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.
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.
Beautiful 3BR Home Near Lake MI
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.
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
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 ￥35,172
￥96,342 total
includes taxes & fees
May 14 - May 15
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior

Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.8 out of 10, Exceptional, (18 reviews)
"Perfect home for our family Christmas get-together. It was a cozy gathering place for our families & kids with space for everyone. Had everything we needed. Minutes from where I grew up and loved the views & proximity to the lake."
United States
Tiffany K.
Lake Michigan Beachfront - King Suite - Game Room
Terrace/patio

Stunning private home hidden in the woods. Can sleep 11 guests

Stunning 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 ￥125,056
￥150,735 total
includes taxes & fees
May 8 - May 9
Stunning private home hidden in the woods. Can sleep 11 guests
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.
The price is ￥54,712
￥121,545 total
includes taxes & fees
May 8 - May 9
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

Watershed Hotel

Watershed Hotel

10/10 Excellent
"The room was fabulous--beautiful view, clean, and comfortable. Breakfast was very basic. Parking was extremely convenient. This was our second time here and we will stay again. Really lovely accommodations."
Karen 1-night trip
Posted 2 hours ago
Watershed Hotel

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
627
Accommodation
266 Vacation Homes
Lowest Price
￥23,953
Highest Price
￥150,735