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Vacation rentals in Sheboygan

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Top-rated vacation rentals in Sheboygan

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Sheboygan
Relaxing 1946 Bungalow-Private room/bathroom
All are welcome. Roomy bedroom/closet with private bathroom located in a spacious sunny house with enclosed garden room, quiet neighborhood 2 short blocks from Lake Michigan. Near downtown, shops, businesses, fishing charters, golf courses, fresh water surfing, parks, hiking/bird watching, restaurants galore, Road America race track, oldest disc golf course in WI, more! Picnic basket, and beach chairs available to use. Two friendly rescue cats in residence and host is vaccinated for COVID.
Guest suite in Sheboygan
Modern + Minimalist 1BR Near Lakeshore Apartment!
Kick back and relax in this calm, stylish space. Only a 3 minute drive to the beautiful lakeshore in Sheboygan, WI. This location is the perfect place to relax or work remotely. This cozy and modern 1BR apartment is fully renovated and is fully equipped for short or long-term stays. Sheboygan is a growing, artsy city with so much to offer. From great food to wonderful summer events, you get all the benefits of a metro city while still in a small town.
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Rental unit in Sheboygan
Sheboygan Surf House "Jetties"
Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly
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Stay near Sheboygan's top sights

Photo of Blue Harbor Resort
Blue Harbor Resort27 locals recommend
Photo of Deland Park
Deland Park22 locals recommend
Photo of Bookworm Gardens
Bookworm Gardens31 locals recommend
Photo of Piggly Wiggly
Piggly Wiggly6 locals recommend
Photo of Texas Roadhouse
Texas Roadhouse3 locals recommend
Photo of Parker John's BBQ & Pizza - Sheboygan
Parker John's BBQ & Pizza - Sheboygan22 locals recommend

Other great vacation rentals in Sheboygan

Townhouse in Sheboygan
Waterfront Townhome with HUGE Rec Room - Sleeps 7
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Guesthouse in Sheboygan
Nautical Themed Guest Suite
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Rental unit in Sheboygan
Modern Upper Apt - Steps from Lake Michigan
Home in Sheboygan
Dog Friendly Blue Door Cottage - Sleeps 6
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Home in Sheboygan
River Home Getaway with River Access - Sleeps 8
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Private room in Sheboygan
Sunny King Bedrm Downtn Sheb w/Bike & Kitchenette
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Rental unit in Sheboygan
Cozy Sheboygan Upper
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Townhouse in Sheboygan
Danz Sheboygan Retreat. Newly Remodeled in 2021.
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Guesthouse in Sheboygan
Moonrise Kingdom surf shack. One block to beach.
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Rental unit in Sheboygan
Heart of Downtown Sheboygan
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Condo in Sheboygan
Beach View Condo near South Pier
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Home in Sheboygan
Relaxing Sheboygan/Kohler Getaway
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Stays in Business Drive North

Rental unit in Sheboygan
The Beach | Sheboygan 2Br/1 Ba
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Rental unit in Sheboygan
Lovely modern two bedroom home with fire pit
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Home in Sheboygan
Close Lake Spacious 1 BDRM entire place guesthouse
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Condo in Sheboygan
Upper Beach View Condo near South Pier
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Stays in James Madison

Rental unit in Sheboygan
Sheboygan Surf House "North Point"
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Rental unit in Sheboygan
The Garden | Sheboygan 2 Br/1Ba, Pet Friendly
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Rental unit in Kohler
The Hemingway on Church - It Tolls For Thee
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Condo in Sheboygan
Riverfront Condo for Rent
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Stays in End Park

Rental unit in Sheboygan
Spotless Apartment Getaway near Downtown
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Guest suite in Sheboygan
Upper Duplex near Lake Michigan
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Condo in Sheboygan
Urban Townhouse
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Home in Sheboygan
Boutique Wellness Retreat - Hot Tub and Fireplace
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Other types of stays on Airbnb

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