Title: Sheboygan Vacation Home Rentals from CA $191: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Sheboygan](https://expedia.ca/Sheboygan-Hotels.d6059814.Travel-Guide-Hotels)[Vacation Rentals in Sheboygan](https://expedia.ca/Sheboygan-Vacation-Rentals.d6059814.Travel-Guide-VacationRentals)[Flights to Sheboygan](https://expedia.ca/Cheap-Flights-To-Sheboygan.d6059814.Travel-Guide-Flights)[Sheboygan Car Rentals](https://expedia.ca/Car-Rentals-In-Sheboygan.d6059814.Car-Rental-Guide)[Sheboygan Vacation Packages](https://expedia.ca/Sheboygan.d6059814.Destination-Travel-Guides) ![Getting out on the jetty to get this photo is just ONE of the perspectives you are presented with when you get down to the lake shore in Sheboygan County. Facing north, the sunrise just appeared to have so many natural colors for this long exposure. Plus, the calm waters looked even more so at 4 seconds. If you get to the eastern side of Wisconsin, in Sheboygan County, heading to the lake is a MUST.](https://images.trvl-media.com/place/6059814/6ee3f5a4-1fa9-4851-859a-f5e938844522.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by John Sukowaty ![](https://images.trvl-media.com/place/6059814/6ee3f5a4-1fa9-4851-859a-f5e938844522.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheboygan vacation homes ![Children's area](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/fb8e2e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/9f8d9d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/75380678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/8fa82c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Cottage in the Woods with Lake Michigan only 300 feet away. [](https://www.expedia.ca/Oostburg-Hotels-Sandalwood-CottageWooded-Acreage-By-The-Lakeshore.h60665977.Hotel-Information) Oostburg 10/10 Exceptional (122 reviews) "Our host was warm and welcoming and our accommodations were wonderful (well appointed and decorated … every detail well thought out)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heidi E. CA $159 CA $196 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Oostburg-Hotels-Sandalwood-CottageWooded-Acreage-By-The-Lakeshore.h60665977.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/97000000/96500000/96496800/96496747/8acd103e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/97000000/96500000/96496800/96496747/cef0fcbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96500000/96496800/96496747/f459431e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96500000/96496800/96496747/34841205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown [](https://www.expedia.ca/Sheboygan-Hotels-3-Blocks-From-Lake-Walk-To-Lake.h96496747.Hotel-Information) Sheboygan 10/10 Exceptional (13 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Riley W. CA $80 CA $191 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Sheboygan-Hotels-3-Blocks-From-Lake-Walk-To-Lake.h96496747.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/107000000/106450000/106445400/106445359/ab2027ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106450000/106445400/106445359/92c1400e_edited_c12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/107000000/106450000/106445400/106445359/26013a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/107000000/106450000/106445400/106445359/9110bcf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown. [](https://www.expedia.ca/Sheboygan-Hotels-Cozy-1-Bedroom-House-In-Sheboygan-Walking-Distance-To-The-Lake-And-Downtown.h106445359.Hotel-Information) Ellis Historical District 9.6/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca S. CA $156 CA $208 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Sheboygan-Hotels-Cozy-1-Bedroom-House-In-Sheboygan-Walking-Distance-To-The-Lake-And-Downtown.h106445359.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/7bb2be7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/4e1662f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/bae072aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/afb7c9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit [](https://www.expedia.ca/Sheboygan-Hotels-Relax-N-Retreat-Near-Lake-MI-W-Fire-Pit.h93001741.Hotel-Information) Sheboygan 10/10 Exceptional (6 reviews) "4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy P. CA $138 CA $249 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Sheboygan-Hotels-Relax-N-Retreat-Near-Lake-MI-W-Fire-Pit.h93001741.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/99000000/98140000/98136500/98136437/5a75bc6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/99000000/98140000/98136500/98136437/067f05a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98140000/98136500/98136437/052bb671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/99000000/98140000/98136500/98136437/c3c88b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city [](https://www.expedia.ca/Sheboygan-Hotels-Pet-Friendly.h98136437.Hotel-Information) Sheboygan 10/10 Exceptional (24 reviews) "Wonderfully close to the lake. Sad there was no off street parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucas T. CA $171 CA $484 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Sheboygan-Hotels-Pet-Friendly.h98136437.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100400000/100391500/100391495/a4ffea08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100400000/100391500/100391495/25e22f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/101000000/100400000/100391500/100391495/433e29a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/101000000/100400000/100391500/100391495/4c2abc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced [](https://www.expedia.ca/Sheboygan-Hotels-The-Suncatcher-Pet-Friendly.h100391495.Hotel-Information) Sheboygan 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Jean S. CA $169 CA $537 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Sheboygan-Hotels-The-Suncatcher-Pet-Friendly.h100391495.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29490000/29486700/29486627/e9b1b28e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29490000/29486700/29486627/a4f5ba25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29490000/29486700/29486627/bb134dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29490000/29486700/29486627/4f8ec037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Esker Ridge Chalet, Pristine Elkhart Solitude [](https://www.expedia.ca/Elkhart-Lake-Hotels-House.h29486627.Hotel-Information) Elkhart Lake 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott G. CA $270 CA $372 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Elkhart-Lake-Hotels-House.h29486627.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/7abf5970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/5db056b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/129e3b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/b0242d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheboygan Riverside Condo [](https://www.expedia.ca/Sheboygan-Hotels-Sheboygan-Riverside-Condo.h120598729.Hotel-Information) Sheboygan CA $156 CA $289 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Sheboygan-Hotels-Sheboygan-Riverside-Condo.h120598729.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/222dec7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/269cd575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/a0a51f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/acf3c1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!! [](https://www.expedia.ca/New-Holstein-Hotels-Cozy-Cottage-Near-Schwarz-Supper-Club.h30666480.Hotel-Information) New Holstein 10/10 Exceptional (173 reviews) "Great place would go back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $275 CA $452 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/New-Holstein-Hotels-Cozy-Cottage-Near-Schwarz-Supper-Club.h30666480.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63730000/63725300/63725280/a06db27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63730000/63725300/63725280/7ae61e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, stereo](https://images.trvl-media.com/lodging/64000000/63730000/63725300/63725280/7c2b0f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63730000/63725300/63725280/78dbe5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful private home hidden in the woods. Can sleep 11 guests [](https://www.expedia.ca/Sheboygan-Hotels-Private-Ranch-Home-Hidden-In-The-Woods-With-Lots-Of-Wildlife-To-View.h63725280.Hotel-Information) Plymouth 10/10 Exceptional (14 reviews) "Very clean and private property! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sherine m. CA $1,084 CA $1,307 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Sheboygan-Hotels-Private-Ranch-Home-Hidden-In-The-Woods-With-Lots-Of-Wildlife-To-View.h63725280.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122160000/122152000/122151929/0408c039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/123000000/122160000/122152000/122151929/dc73ef23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122160000/122152000/122151929/963511b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122160000/122152000/122151929/553e1798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake. [](https://www.expedia.ca/Campbellsport-Hotels-Brand-New-Modern.h122151929.Hotel-Information) Campbellsport CA $1,221 CA $2,040 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Campbellsport-Hotels-Brand-New-Modern.h122151929.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/4b45b7fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, video library](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/34951186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/e64321dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, video library](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/d7b56df1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America [](https://www.expedia.ca/Reedsville-Hotels-Behnkes-Country-Center.h36361192.Hotel-Information) Reedsville 9.8/10 Exceptional (32 reviews) "Great place for family to stay for wedding of grandson. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn C. CA $407 CA $651 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Reedsville-Hotels-Behnkes-Country-Center.h36361192.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/3fefe856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/1e1f5c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/2d2f2f02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/64699ec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Road America, Elkhart Lake! [](https://www.expedia.ca/Elkhart-Lake-Hotels-Road-America.h104873026.Hotel-Information) Elkhart Lake 7.0/10 Good (2 reviews) CA $237 CA $505 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Elkhart-Lake-Hotels-Road-America.h104873026.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107080000/107077100/107077098/282af831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107080000/107077100/107077098/4906fd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/108000000/107080000/107077100/107077098/5a41b30e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/108000000/107080000/107077100/107077098/26d9139c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler [](https://www.expedia.ca/Kiel-Hotels-Luxury-Historic-Rental-In-Kiel-Minutes-To-Elkhart-Lake.h107077098.Hotel-Information) Kiel 10/10 Exceptional (3 reviews) "Wonderful place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen & Mark G. CA $489 CA $835 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Kiel-Hotels-Luxury-Historic-Rental-In-Kiel-Minutes-To-Elkhart-Lake.h107077098.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/c099779d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/400683dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/f99a3d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/e6396f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Min to Road America, outdoor deck, grill, & fire table [](https://www.expedia.ca/Plymouth-Hotels-Spacious.h118167786.Hotel-Information) Plymouth 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt W. CA $522 CA $1,111 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Plymouth-Hotels-Spacious.h118167786.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114560000/114552400/114552384/37b2bc5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114560000/114552400/114552384/c5ebddb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114560000/114552400/114552384/6599d1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114560000/114552400/114552384/76e34232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 min from Road America. Great yard and plenty of parking [](https://www.expedia.ca/Elkhart-Lake-Hotels-Spacious-5-Bedroom-House-In-Fantastic-Elkhart-Lake-With-AC.h114552384.Hotel-Information) Elkhart Lake 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul & Jacqleene M. CA $1,062 CA $1,605 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Elkhart-Lake-Hotels-Spacious-5-Bedroom-House-In-Fantastic-Elkhart-Lake-With-AC.h114552384.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103750000/103741300/103741253/1ad16559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103750000/103741300/103741253/440c9886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/104000000/103750000/103741300/103741253/f0c96391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103750000/103741300/103741253/40805fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More. [](https://www.expedia.ca/Sheboygan-Hotels-Luxury-Lake-House-4Bed-2Bath-NEW-Renovation-2023-Walk-To-Beach.h103741253.Hotel-Information) Sheboygan 10/10 Exceptional (12 reviews) "Everything was clean and spacious. Had a great time and would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brad T. CA $568 CA $1,088 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Sheboygan-Hotels-Luxury-Lake-House-4Bed-2Bath-NEW-Renovation-2023-Walk-To-Beach.h103741253.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83450000/83447100/83447035/9780c3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83450000/83447100/83447035/82862fba_edited_bb30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/84000000/83450000/83447100/83447035/9a8dbf7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83447100/83447035/21dc8244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Property with Hot Tub, Jukebox, Sleeps 10 [](https://www.expedia.ca/Cascade-Hotels-Indoor-Sauna.h83447035.Hotel-Information) Cascade 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta V. CA $425 CA $788 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Cascade-Hotels-Indoor-Sauna.h83447035.Hotel-Information) ![TV, DVD player](https://images.trvl-media.com/lodging/90000000/89810000/89808600/89808528/w1988h1120x224y5-fc815b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89808600/89808528/18ec8126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89808600/89808528/49063710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89808600/89808528/c339ec2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 2 Bedroom Duplex [](https://www.expedia.ca/Fond-Du-Lac-Hotels-Beautiful-2-Bedroom-Duplex.h89808528.Hotel-Information) Fond du Lac 9.8/10 Exceptional (16 reviews) "Nice house and easy to find" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary G. CA $152 CA $362 total includes taxes & fees Feb 19 - Feb 20 [](https://www.expedia.ca/Fond-Du-Lac-Hotels-Beautiful-2-Bedroom-Duplex.h89808528.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78120000/78112100/78112064/4adde574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathtub, hair dryer, towels](https://images.trvl-media.com/lodging/79000000/78120000/78112100/78112064/9caa2422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/79000000/78120000/78112100/78112064/30b1b4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78112100/78112064/685f3ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ｄｅｓｔｉｎａｔｉｏｎ Ｄｏｗｎｔｏｗｎ [](https://www.expedia.ca/Oshkosh-Hotels-.h78112064.Hotel-Information) Oshkosh 9.0/10 Wonderful (11 reviews) "Nicely remodeled house. Lots of construction surrounding the house." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole T. CA $117 CA $405 total includes taxes & fees Feb 19 - Feb 20 [](https://www.expedia.ca/Oshkosh-Hotels-.h78112064.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=6059814&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6059814) ## Find vacation rentals that suit your style Villas [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=CONDO) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Sheboygan%2C+Wisconsin%2C+United+States+of+America®ionId=6059814&latLong=43.749832%2C-87.712982&adults=2&startDate=2026-05-13&d1=2026-05-13&endDate=2026-05-16&d2=2026-05-16&lodging=APART_HOTEL) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheboygan-Private-Vacation-Homes.d6059814-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheboygan-Private-Vacation-Homes.d6059814-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Sheboygan Hotel Reviews ![Beach front luxury spacious villa !](https://images.trvl-media.com/lodging/90000000/89980000/89975300/89975203/13e75035_y.jpg) ### Beach front luxury spacious villa ! 10/10 Excellent "Host was great with answering questions. The condo feels like a home and after having rented condos at blue harbor resort for 20 years we enjoyed this vibe so much more. The host must be a foodie because she even had a muddler! We will be back again !!! " [](https://expedia.ca/Sheboygan-Hotels-Beach-Front-Luxury-Spacious-Villa.h89975203.Hotel-Information) ![Grandstay Residential Suites Hotel - Sheboygan](https://images.trvl-media.com/lodging/3000000/2010000/2005100/2005043/402d6f8a_y.jpg) ### Grandstay Residential Suites Hotel - Sheboygan 10/10 Excellent "Room was very clean and perfect for a downtown stay" [](https://expedia.ca/Sheboygan-Hotels-Grandstay-Residential-Suites-Hotel-Sheboygan.h2005043.Hotel-Information) ![Watershed Hotel](https://images.trvl-media.com/lodging/84000000/83550000/83541900/83541884/521022c3_y.jpg) ### Watershed Hotel 10/10 Excellent "The room was very spacious, extremely clean, and bed was very comfortable. Convenient location and Bailey (& Dax) were very welcoming and friendly. " [](https://expedia.ca/Sheboygan-Hotels-Watershed-Hotel.h83541884.Hotel-Information) ![Holiday Inn Express Sheboygan-Kohler by IHG](https://images.trvl-media.com/lodging/1000000/50000/43200/43134/a3806c9c_y.jpg) ### Holiday Inn Express Sheboygan-Kohler by IHG 10/10 Excellent "The room was spotless. The bed was very comfortable and the shower was amazing." [](https://expedia.ca/Sheboygan-Hotels-Holiday-Inn-Express-Sheboygan-Kohler.h43134.Hotel-Information) ![Fairfield Inn & Suites by Marriott Sheboygan](https://images.trvl-media.com/lodging/45000000/44220000/44215800/44215800/ebb68251_y.jpg) ### Fairfield Inn & Suites by Marriott Sheboygan 10/10 Excellent "Clean and comfy room. Smooth check in. Nice breakfast and bar. " [](https://expedia.ca/Sheboygan-Hotels-Fairfield-Inn-Suites-By-Marriott-Sheboygan.h44215800.Hotel-Information) ![Harbor Winds Hotel](https://images.trvl-media.com/lodging/1000000/860000/859000/858919/7355c06d_y.jpg) ### Harbor Winds Hotel 10/10 Excellent "Nice stay! Lila, at the desk was wonderful. The room was clean and the beds comfortable." [](https://expedia.ca/Sheboygan-Hotels-Harbor-Winds-Hotel-Sheboygan.h858919.Hotel-Information) ![Comfort Inn & Suites Sheboygan I-43](https://images.trvl-media.com/lodging/1000000/930000/921400/921389/2dd9d6b5_y.jpg) ### Comfort Inn & Suites Sheboygan I-43 10/10 Excellent "Location was convenient and easy to find. Check-in staff was friendly and welcoming. I found the room to be extremely clean and smelling fresh. The bed was very comfortable and allowed me a good night’s rest. Appreciate the laminate flooring and lack of carpet - gives it a much more sanitary feel. Will definitely consider this location again in the future." [](https://expedia.ca/Sheboygan-Hotels-Sleep-Inn-Suites-Sheboygan-I-43.h921389.Hotel-Information) ![AmericInn by Wyndham Sheboygan](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/ea3b9a85_y.jpg) ### AmericInn by Wyndham Sheboygan 10/10 Excellent "Couldn’t complain. " [](https://expedia.ca/Sheboygan-Hotels-AmericInn-By-Wyndham-Sheboygan.h663055.Hotel-Information) ![Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX](https://images.trvl-media.com/lodging/114000000/113530000/113521100/113521028/dffbb42a_y.jpg) ### Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX 10/10 Excellent "The only trouble with this place is it had too many amenities. too much to do. The solution is we will just go again. We got the place specifically for the pool. Online pictures don't do it justice. The pool hot tub area was exquisite. Very well maintained. The game room/arcade was something we didn't care much about till will we got there. ended up spending lots of time there. Fun for all ages. In general, the place is huge, space for all very clean and well maintained. The beds are in good shape. And loved all the fireplaces. There are always some questions you have and the staff/team was very responsive. The #1 thing that impressed me the most was the digital guidebook they sent before our arrival. No VRBO location has ever done that! And it made our arrival so much smoother!! Can't wait to go back!" [](https://expedia.ca/Sheboygan-Hotels-Baronwood-Oasis-Indoor-PoolSpa-Arcades-16beds-LUX.h113521028.Hotel-Information) ## Find out more about Sheboygan ## Sheboygan Vacation Homes information | Number of reviews | 569 | | ----------------- | ------------------ | | Accommodation | 262 Vacation Homes | | Lowest Price | CA $191 | | Highest Price | CA $2,040 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Adell Hotels ](https://www.expedia.ca/Adell-Hotels.d553248634983118883.Travel-Guide-Hotels) - [Hotels near Blackwolf Run ](https://www.expedia.ca/Blackwolf-Run-Hotels.0-l6093963-0.Travel-Guide-Filter-Hotels) - [Hotels near Blue Harbor Resort & Conference Center Water Park ](https://www.expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Hotels.0-l553248621532659437-0.Travel-Guide-Filter-Hotels) - [Cascade Hotels ](https://www.expedia.ca/Cascade-Hotels.d6023613.Travel-Guide-Hotels) - [Farmstay in Cedar Grove ](https://www.expedia.ca/Cedar-Grove-Agritourism.d3000461532-aaAgritourism.Travel-Guide-Accommodation) - 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