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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, (119 reviews)
"Lovely place and quiet"
United States
grandma d.
The price is ¥18,974
¥23,354 total
includes taxes & fees
Jan 20 - Jan 21
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
4.0 star property
Fond du Lac
10.0 out of 10, Exceptional, (1 review)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
United States
Brenda J.
The price is ¥284,616
¥516,504 total
includes taxes & fees
Jan 26 - Jan 27
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Hot Tub, Fire Pit, Point Beach & Neshotah Beach

Hot Tub, Fire Pit, Point Beach & Neshotah Beach
2.0 star property
Two Rivers
Hot Tub, Fire Pit, Point Beach & Neshotah Beach

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.
2.0 star property
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 ¥18,184
¥24,229 total
includes taxes & fees
Jan 20 - Jan 21
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, (12 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 ¥9,171
¥20,998 total
includes taxes & fees
Jan 20 - Jan 21
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

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, (32 reviews)
"Adorable very clean cottage right on the river. Nice backyard with beautiful views and if you bring your furry friend, plenty of room for your doggie to roam and play out back. Close to beautiful Neshota Beach and lots of dining options. "
United States
Pamela S.
The price is ¥11,954
¥33,669 total
includes taxes & fees
Jan 20 - Jan 21
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

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 ¥15,369
¥28,213 total
includes taxes & fees
Jan 20 - Jan 21
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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, (22 reviews)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
The price is ¥19,923
¥56,711 total
includes taxes & fees
Jan 20 - Jan 21
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

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 ¥16,603
¥58,508 total
includes taxes & fees
Jan 20 - Jan 21
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan Riverside Condo

Sheboygan Riverside Condo
2.0 star property
Sheboygan
The price is ¥18,658
¥34,034 total
includes taxes & fees
Jan 25 - Jan 26
Sheboygan Riverside Condo

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 ¥32,019
¥52,965 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

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
2.0 star property
Kiel
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful place! "
United States
Colleen & Mark G.
The price is ¥56,923
¥96,420 total
includes taxes & fees
Jan 20 - Jan 21
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

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 ¥126,496
¥152,470 total
includes taxes & fees
Jan 20 - Jan 21
Beautiful private home hidden in the woods. Can sleep 11 guests

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

Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
2.0 star property
Campbellsport
The price is ¥126,370
¥213,059 total
includes taxes & fees
Jan 20 - Jan 21
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (58 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 ¥31,466
¥42,873 total
includes taxes & fees
Jan 20 - Jan 21
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 ¥47,436
¥76,236 total
includes taxes & fees
Jan 20 - Jan 21
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is ¥27,671
¥59,063 total
includes taxes & fees
Jan 20 - Jan 21
Road America, Elkhart Lake!

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 ¥55,342
¥122,945 total
includes taxes & fees
Jan 20 - Jan 21
3 Min to Road America, outdoor deck, grill, & fire table

Spacious Property with Hot Tub, Jukebox, Sleeps 9

Spacious Property with Hot Tub, Jukebox, Sleeps 9
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.
The price is ¥44,432
¥82,242 total
includes taxes & fees
Jan 21 - Jan 22
Spacious Property with Hot Tub, Jukebox, Sleeps 9

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 ¥130,449
¥195,343 total
includes taxes & fees
Feb 1 - Feb 2
5 min from Road America. Great yard and plenty of parking
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
559
Accommodation
262 Vacation Homes
Lowest Price
¥20,998
Highest Price
¥516,504