Holiday rentals in Sheboygan

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Top-rated holiday rentals in Sheboygan

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Guest favourite

Home in Sheboygan

4.96 out of 5 average rating, 113 reviews

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

Guest favourite

Home in Elkhart Lake

4.91 out of 5 average rating, 217 reviews

The LODGE in Elkhart Lake

Rustic modern home w/ hot tub, arcade and fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, and the Kettle Moraine are all at your doorstep. You will be staying in a cute & cozy home 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore and enjoy nature. We are also only 4 miles from Road America. 2 bedroom, 2 bathroom. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. We got your bases covered!

Guest favourite

Home in Sheboygan

4.82 out of 5 average rating, 226 reviews

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

Guest favourite

Home in Sheboygan

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

3 BR. 3 BA. Fully furnished. Granite counters and stainless steel appliances in large kitchen overlooking the lake. King and Queen suites with 2nd King and full Bath. Sleeps 6, but very large sofa. Washer/Dryer. Lake Michigan views throughout, Pool table room, work space, 2 levels of patios. Sits on landscaped sand dunes and beach. 10 min drive to Black Wolf Run Golf and resort. Front row for boat races from 2 decks. Den with large fireplace. Dining table overlooking lake + lighthouse.

Guest favourite

Home in Sheboygan

4.96 out of 5 average rating, 128 reviews

Beach and golf house

This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic Ellis district on the shores of beautiful Lake Michigan. The home is a 2 or 3 minute walk to Deland Beach and the Sheboygan Marina and lighthouse. A short drive to world class golfing at Whistling Straights, Black Wolf Run and The Bull. Road America is also a short 20 minute drive. Located half way between Green Bay and Milwaukee for those Packer and Brewer fans.

Guest favourite

Home in Oostburg

4.96 out of 5 average rating, 154 reviews

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan completely private surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room and living room entertainment space, den with see thru log fired fireplace, screened in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and row boat are available for the boating enthusiast, with life jackets and other floating devices.

Guest favourite

Apartment in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise: Monthly Rates Available!

Starting 12/1/2024 Rent for an extended stay. Monthly rates until 4/1/2025 Explore your dream destination in this stunning 4-bedroom beachfront condo! With 7 beds and 3 full baths, it's perfect for relaxation. Luxurious master suite, 2-person jacuzzi tub, balcony boasting picturesque courtyard and lake views, a TV, and a gas fireplace. Convenience meets comfort with an in-unit washer/dryer and a fully stocked kitchen, providing everything you need for a seamless stay.

Guest favourite

Apartment in Sheboygan

4.97 out of 5 average rating, 137 reviews

Downtown Beachside Condo with Lake Michigan Views

You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals. A deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art, & exquisite restaurants - walkable from the condo.

Guest favourite

Home in Sheboygan

4.94 out of 5 average rating, 191 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Guest favourite

Home in Oostburg

4.96 out of 5 average rating, 186 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 133 reviews

Lakeview Beach Bungalow - With outdoor Hot Tub!

Beautifully updated beach house just one block off of Lake Michigan. Enjoy the newly landscaped backyard with pergola and 6 person Hot Tub! Watch the sunrise and sunset from the second floor master balcony. Walk to the lake across the street and enjoy the wind surfers and gorgeous scenery. Close to downtown and major parks. This three bedroom home will impress. Tastefully decorated. First floor laundry. Large bathroom with deep soaking tub.

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 137 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.