Title: Sheboygan Vacation Home Rentals from CA $235: 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) ![](https://mediaim.expedia.com/destination/2/7f3f9b687c1d6e62465acab73585ba2b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by ed lee schneider # Sheboygan Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6059814&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Sheboygan Vacation Homes ![Interior](https://images.trvl-media.com/lodging/67000000/66300000/66298400/66298380/ed393a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66300000/66298400/66298380/w1023h765x0y0-b5ab676f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66300000/66298400/66298380/4a0cc7a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66300000/66298400/66298380/20f696ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gleason's Chouse Campbellsport 10/10 Exceptional (40) "The house was such a unique and fun place to stay, we had such a great weekend and experience there. My spouse is already talking about coming back someday soon. The neighborhood felt safe and it was easy to get around to any place we needed to. It was clean and stocked with extra amenities that anyone might need on a trip. " CA $188 CA $269 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Sheboygan-Hotels-Gleasons-Chouse.h66298380.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120650000/120646900/120646856/0f426a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/121000000/120650000/120646900/120646856/0ece2601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120650000/120646900/120646856/3bf70368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120650000/120646900/120646856/0cb47b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beach town bungalow Sheboygan CA $133 CA $275 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Sheboygan-Hotels-The-Beach-Town-Bungalow.h120646856.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107080000/107077100/107077098/da2a9699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/108000000/107080000/107077100/107077098/47a4689d.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) ### Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler Kiel 10/10 Exceptional (3) "Wonderful place! " CA $502 CA $851 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Kiel-Hotels-Luxury-Historic-Rental-In-Kiel-Minutes-To-Elkhart-Lake.h107077098.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76960000/76951300/76951291/e82f61e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/77000000/76960000/76951300/76951291/df44febe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76960000/76951300/76951291/40c94df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76960000/76951300/76951291/22aa48c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyatt's Country Home - King Bed! Plymouth 10/10 Exceptional (17) "Beautiful property and perfect location!" CA $188 CA $339 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Plymouth-Hotels-Wyatts-Country-Home-King-Bed.h76951291.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39410000/39407400/39407367/5e60fbb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39410000/39407400/39407367/a41d130e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39410000/39407400/39407367/4c2bc681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/40000000/39410000/39407400/39407367/d6af5b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater Fond du Lac 10/10 Exceptional (1) "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 ." CA $2,511 CA $4,557 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Fond-Du-Lac-Hotels-Best-House-In-Wisconsin-Live-Like-A-STAR-VRBO-Luxury-Huge-Bar-Movie-Theater.h39407367.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114430000/114428300/114428264/964732a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114430000/114428300/114428264/04046015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114430000/114428300/114428264/5dd96205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114430000/114428300/114428264/98669c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI Sheboygan 10/10 Exceptional (2) "Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself." CA $159 CA $279 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Sheboygan-Hotels-Eclectic-3-BR-Lower-W-King-Bed-Pack-N-Play-Fire-Pit-Near-Lake-MI.h114428264.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120600000/120598900/120598863/5c63a88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120600000/120598900/120598863/ba42017b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120600000/120598900/120598863/009b2147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/121000000/120600000/120598900/120598863/11a1b8e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surfside Retreat – Walk to Lake Ellis Historical District CA $133 CA $363 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Sheboygan-Hotels-Surfside-Retreat-Walk-To-Lake.h120598863.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119730000/119720400/119720342/7a1ae297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119730000/119720400/119720342/48ba4ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119730000/119720400/119720342/e23f5bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119730000/119720400/119720342/73e493a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Suites #1 Brillion CA $264 CA $416 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Brillion-Hotels-Luxury-Suites-1.h119720342.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) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/fae9f009.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) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/31000000/30670000/30666500/30666480/d6bc37bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!! New Holstein 10/10 Exceptional (173) "Great place would go back" CA $283 CA $467 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/New-Holstein-Hotels-Cozy-Cottage-Near-Schwarz-Supper-Club.h30666480.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114430000/114427300/114427210/0a3e40d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114430000/114427300/114427210/b362e963.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/115000000/114430000/114427300/114427210/237ab6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114430000/114427300/114427210/53617650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan Sheboygan 9.8/10 Exceptional (6) "We found this location to be the perfect balance during our stay. We were a short drive away from all the places we hoped to go. Downtown, shopping, and the coast were just minutes away. Despite this luxury, the neighborhood we were in was quiet, private and removed from the hustle of crowds and traffic. The property was very well cared for and beautifully decorated. We all had plenty of room to stretch out and prepare for an event we were attending. Grabbing a snack or a meal was a breeze with... CA $143 CA $257 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheboygan-Hotels-Coastal-3-BR-Lower-Near-Lake-MI-And-Downtown-Sheboygan.h114427210.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67530000/67522900/67522866/365f259e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67530000/67522900/67522866/91198089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/68000000/67530000/67522900/67522866/9c94390d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/68000000/67530000/67522900/67522866/c99a0bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach Two Rivers 9.8/10 Exceptional (37) "Loved it. Cute place, good parking, close to everything." CA $173 CA $331 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Two-Rivers-Hotels-Cates-Place-Charming-Home-Just-Minutes-From-Ice-Age-Trail-Neshotah-Beach.h67522866.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/51388349.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) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/8515ff90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/119000000/118170000/118167800/118167786/29cdfe16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Min to Road America, outdoor deck, grill, & fire table Plymouth 10/10 Exceptional (1) "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. " CA $488 CA $1,085 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Plymouth-Hotels-Spacious.h118167786.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/1e1f5c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/9f5591c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104880000/104873100/104873026/w740h554x230y0-2b2cea69.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) ### Road America, Elkhart Lake! Elkhart Lake CA $244 CA $523 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Elkhart-Lake-Hotels-Road-America.h104873026.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/510f3a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/7abf5970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/b42323eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120600000/120598800/120598729/58570507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheboygan Riverside Condo Sheboygan CA $223 CA $373 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheboygan-Hotels-Sheboygan-Riverside-Condo.h120598729.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/w2736h1833x0y0-a5c6be54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/80b7b7c3.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) ![Spa](https://images.trvl-media.com/lodging/61000000/60670000/60666000/60665977/9f8d9d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Cottage in the Woods with Lake Michigan only 300 feet away. Oostburg 10/10 Exceptional (111) "We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process." CA $195 CA $235 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Oostburg-Hotels-Sandalwood-CottageWooded-Acreage-By-The-Lakeshore.h60665977.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/64000000/63730000/63725300/63725280/w1320h738x0y0-eb29369e.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) ![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) ### Beautiful private home hidden in the woods. Can sleep 11 guests Plymouth 10/10 Exceptional (14) "This VRBO was everything that the listing described and more. The host was very easy to communicate with and helped make sure we had a great stay." CA $912 CA $1,099 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Sheboygan-Hotels-Private-Ranch-Home-Hidden-In-The-Woods-With-Lots-Of-Wildlife-To-View.h63725280.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) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/30000000/29490000/29486700/29486627/ab1714ce.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/bc75676b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Esker Ridge Chalet, Pristine Elkhart Solitude Elkhart Lake 10/10 Exceptional (58) "Wonderful place, so quiet and nature surrounding the location. So close to Elkhart Lake and yet you wouldn't realize it when on the property. Five Stars!" CA $278 CA $384 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Elkhart-Lake-Hotels-House.h29486627.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/1dd79330.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) ![Exterior](https://images.trvl-media.com/lodging/37000000/36370000/36361200/36361192/d080c5dc.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) ### Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America Reedsville 9.8/10 Exceptional (32) "Great place for family to stay for wedding of grandson. " CA $419 CA $673 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Reedsville-Hotels-Behnkes-Country-Center.h36361192.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96660000/96656000/96655970/6861f53c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96660000/96656000/96655970/6137c97e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96660000/96656000/96655970/2f0700f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/97000000/96660000/96656000/96655970/91c6b9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LUX Uptown Escape - The Trester Sheboygan 9.4/10 Exceptional (10) "Historic beauty of a home. Loved being able to walk to restaurants, art museum and more. Wonderful accommodations. " CA $174 CA $336 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Sheboygan-Hotels-LUX-Uptown-Escape-The-Trester.h96655970.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/43064d23.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) ![Dining](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/7bb2be7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93010000/93001800/93001741/7189b2d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit Sheboygan 10/10 Exceptional (2) "4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping" CA $211 CA $346 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Sheboygan-Hotels-Relax-N-Retreat-Near-Lake-MI-W-Fire-Pit.h93001741.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=2025-10-23&endDate=2025-10-24®ionId=6059814&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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 ![Grandstay Residential Suites Hotel - Sheboygan](//images.trvl-media.com/lodging/3000000/2010000/2005100/2005043/402d6f8a_y.jpg) ### Grandstay Residential Suites Hotel - Sheboygan 10/10 Excellent "Room was very spacious and clean! I did not hear any of the other guests and the bed was very comfortable. I was in Sheboygan for a wedding at the Berkshire so it was nice to be across the street and could walk to the venue as well as to a number of the places downtown. " [](https://expedia.ca/Sheboygan-Hotels-Grandstay-Residential-Suites-Hotel-Sheboygan.h2005043.Hotel-Information) ![Holiday Inn Express Sheboygan-Kohler by IHG](//images.trvl-media.com/lodging/1000000/50000/43200/43134/a3806c9c_y.jpg) ### Holiday Inn Express Sheboygan-Kohler by IHG 10/10 Excellent "It was nice and staff was very nice and helpful " [](https://expedia.ca/Sheboygan-Hotels-Holiday-Inn-Express-Sheboygan-Kohler.h43134.Hotel-Information) ![Comfort Inn & Suites Sheboygan I-43](//images.trvl-media.com/lodging/1000000/930000/921400/921389/2dd9d6b5_y.jpg) ### Comfort Inn & Suites Sheboygan I-43 10/10 Excellent "Everything was clean and service was friendly " [](https://expedia.ca/Sheboygan-Hotels-Sleep-Inn-Suites-Sheboygan-I-43.h921389.Hotel-Information) ![Harbor Winds Hotel](//images.trvl-media.com/lodging/1000000/860000/859000/858919/7355c06d_y.jpg) ### Harbor Winds Hotel 10/10 Excellent "Management and staff was excellent very helpful! " [](https://expedia.ca/Sheboygan-Hotels-Harbor-Winds-Hotel-Sheboygan.h858919.Hotel-Information) ![La Quinta Inn by Wyndham Sheboygan](//images.trvl-media.com/lodging/1000000/40000/40000/39976/0c381b2f_y.jpg) ### La Quinta Inn by Wyndham Sheboygan 10/10 Excellent "Everything was great " [](https://expedia.ca/Sheboygan-Hotels-La-Quinta-Inn-By-Wyndham-Sheboygan.h39976.Hotel-Information) ![Watershed Hotel](//images.trvl-media.com/lodging/84000000/83550000/83541900/83541884/521022c3_y.jpg) ### Watershed Hotel 10/10 Excellent "Very nice staff, so clean, great room and breakfast choices" [](https://expedia.ca/Sheboygan-Hotels-Watershed-Hotel.h83541884.Hotel-Information) ![Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home](//images.trvl-media.com/lodging/58000000/57700000/57698400/57698316/584b99f9_y.jpg) ### Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home 10/10 Excellent "Everything was perfect, would highly recommended. " [](https://expedia.ca/Sheboygan-Hotels-Sheboygan-Waterfront-3-Bedroom-25-Bathroom-Home.h57698316.Hotel-Information) ![Quality Inn Sheboygan North I-43](//images.trvl-media.com/lodging/1000000/20000/18000/17917/d6bb0d42_y.jpg) ### Quality Inn Sheboygan North I-43 10/10 Excellent "Clean and quiet" [](https://expedia.ca/Sheboygan-Hotels-Quality-Inn.h17917.Hotel-Information) ![Beach front luxury spacious villa !](//images.trvl-media.com/lodging/90000000/89980000/89975300/89975203/13e75035_y.jpg) ### Beach front luxury spacious villa ! 10/10 Excellent "Beautiful view and relaxing weekend! " [](https://expedia.ca/Sheboygan-Hotels-Beach-Front-Luxury-Spacious-Villa.h89975203.Hotel-Information) ## Find out more about Sheboygan ## Sheboygan Vacation Homes information | Number of reviews | 499 | | --- | --- | | Accommodation | 265 Vacation Homes | | Lowest Price | CA $235 | | Highest Price | CA $4,557 | ## 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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