Vacation rentals in Sheboygan

A deck area features white railings and two light blue Adirondack chairs, positioned for relaxation. A patterned outdoor rug is laid beneath, providing a comfortable foundation. Lush greenery and trees are visible in the background, offering a tranquil view of the surrounding landscape.

4.97 out of 5 average rating, 115 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!

4.91 out of 5 average rating, 236 reviews

A scenic outdoor area features a bench overlooking a lush green landscape. Tall trees and dense shrubs create a natural backdrop, while a grassy expanse invites relaxation. A wooden fence outlines the area, enhancing the tranquil setting.

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

Rustic modern home w/ hot tub, arcade & fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, & the Kettle Moraine are all at your doorstep. This cozy home is 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore & enjoy nature. Only 4 miles from Road America. 2 bedroom w/ 2 extra sofa sleepers & 2 baths. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. Perfect base camp. We got your bases covered

4.97 out of 5 average rating, 279 reviews

A single-story cottage is surrounded by vibrant greenery and flower beds. Large windows allow natural light to fill the space, and a stone pathway leads up to the entrance, inviting guests to explore the serene outdoor setting.

Cottage in Oostburg

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

The two-story home features a charming yellow exterior with white trim and a red metal roof. Flower baskets hang from the porch, which is framed by neatly manicured bushes and vibrant landscaping. A sidewalk leads to the entrance, enhancing accessibility.

4.83 out of 5 average rating, 247 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!

4.92 out of 5 average rating, 103 reviews

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

4.96 out of 5 average rating, 129 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.

A spacious outdoor deck is shown, featuring a shaded table with colorful umbrellas. Surrounding the area are mature trees and a clear view of Lake Michigan. The deck's expansive surface offers ample seating and is designed for relaxation and outdoor dining.

4.96 out of 5 average rating, 155 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.

A game room is highlighted by retro arcade games and vibrant wall graphics. Bright colored arcade machines, including a shuffleboard and skee ball, stand out against a dark, playful backdrop. Warm lighting enhances the inviting atmosphere for entertainment and socializing.

4.98 out of 5 average rating, 196 reviews

River Ridge-HOT TUB, Games, Luxury-10 bed, 5 STARS

The search is over, you have found the PERFECT getaway at River Ridge South! The moment you pull in, you will become instant hero for planning the ultimate retreat. This property has something for everyone! Beautiful seclusive country home (3800 sq ft) on 4 acres of a pristine and manicured lawn with the Onion River passing through it. This home is THE perfect countryside retreat for large group gatherings with three levels of finished space and great outdoor amenities.

4.97 out of 5 average rating, 144 reviews

Condo in Sheboygan

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.

The exterior of the home features a spacious deck with outdoor seating and a dining table. Large glass doors offer views into the interior, while landscaped areas with shrubs and flowers surround the base. The image captures a clear blue sky overhead.

4.94 out of 5 average rating, 196 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.

A hammock is set between two trees on a grassy area, facing the serene view of Lake Michigan. A spacious guest home with large windows is visible in the background, framed by lush greenery and a clear blue sky.

4.96 out of 5 average rating, 187 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...

4.97 out of 5 average rating, 139 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.

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Popular amenities for Sheboygan vacation rentals

Laptop-friendly workspace

Stay near Sheboygan's top sights

John Michael Kohler Arts Center60 locals recommend

Il Ritrovo53 locals recommend

Trattoria Stefano44 locals recommend

Field to Fork44 locals recommend

Blackwolf Run Golf Course43 locals recommend

3 Sheeps Brewing Company42 locals recommend

Dog friendly vacation rentals in Sheboygan

Apartment in New Holstein

A comfortable seating area is presented with two sofas featuring soft neutral tones and decorative pillows. A wooden coffee table holds magazines, while a light rug enhances the warm atmosphere. A queen-sized bed is visible in the background, with natural light filtering through a nearby window.

4.98 out of 5 average rating, 49 reviews

Parkside Retreat | Minutes from Elkhart Lake

A spacious dining area features a wooden table surrounded by six modern chairs. A vibrant area rug adds color to the floor, while a ceiling fan is mounted above. A decorative mirror and potted plant enhance the room's decor, with light flooding in from nearby windows.

4.9 out of 5 average rating, 126 reviews

Spacious Home Near Lake MI w/ Fire Pit

4.97 out of 5 average rating, 101 reviews

A wooden dock extends into a tranquil lake, featuring a bench at its end. The water reflects soft hues from the sunrise, with a mist gently rising in the distance. Tree-lined shores provide a serene backdrop.

Chalet in Campbellsport

Long Lake Chalet

Apartment in Elkhart Lake

The exterior of a two-story building is illuminated by warm lights at dusk. A welcoming entrance is marked by a covered porch and flanked by decorative pumpkins. An American flag hangs beside the front door, while a parked vehicle is visible in the foreground.

4.96 out of 5 average rating, 141 reviews

Schoolhouse Straight Inn

4.98 out of 5 average rating, 139 reviews

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

Apartment in Sheboygan

Lovely modern two bedroom home with fire pit

A comfortable living room showcases a reclining sectional and two armchairs with a plaid pattern. A coffee table sits centrally, accompanied by a decorative throw and a plant. Natural light filters through the window, accentuating the warm decor and smart TV mounted on the wall.

4.95 out of 5 average rating, 221 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

4.96 out of 5 average rating, 124 reviews

Good VIBES On the Third COAST- Pets Welcome

4.82 out of 5 average rating, 455 reviews

The exterior of the Carriage House is shown, featuring a charming gray-brown facade with a garage door. A white entrance door is visible, framed by greenery and blooming white flowers in the foreground, enhancing the inviting atmosphere of the home.

Guesthouse in Sheboygan

Carriage House Sheboygan, garage parking included!

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Family friendly vacation rentals in Sheboygan

4.98 out of 5 average rating, 276 reviews

A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.

Apartment in Waldo

The Blue Cobb House

The living room features a light, airy space with a large window offering a view of Lake Michigan. A cozy white sofa is complemented by a striped chair, and a wooden coffee table holds decorative items. Soft lighting illuminates the room, enhancing its inviting atmosphere.

4.96 out of 5 average rating, 125 reviews

Bright and Beautiful Lake Escape

The exterior view of the home presents a combination of stone and wood siding, accentuated by large windows that showcase the scenic surroundings. A pathway of stepping stones leads to a covered porch, framed by well-maintained grass and nearby trees.

4.72 out of 5 average rating, 18 reviews

Summit Ranch - Elkhart Lake/Road America- 3 mins

An outdoor fire pit area is surrounded by vibrant red chairs arranged in a circle. The sun sets over Lake Michigan, casting a warm glow on the grassy landscape, which gently slopes towards the beach. Additional seating is visible nearby.

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

4.86 out of 5 average rating, 139 reviews

A welcoming living area features two comfortable sofas adorned with striped cushions and a wooden coffee table in the center. Natural light enters through a window with sheer curtains, creating a bright and inviting space. Light-toned hardwood floors complete the room.

Home in New Holstein

Growe's Guest House - just like Grandma's!

4.98 out of 5 average rating, 125 reviews

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

4.89 out of 5 average rating, 64 reviews

The front exterior of a ranch-style home is shown, featuring a central entrance with an awning and windows framed in dark shutters. Lush green grass surrounds the home, and trees provide a natural backdrop. A driveway leads up to a garage on the left.

Home in Elkhart Lake

Elkhart Lake Village house

The exterior of a two-story, tan house is displayed, featuring a welcoming front porch with five metal chairs arranged for comfortable seating. A concrete path leads to the porch, while landscaped areas with rocks and foliage enhance the surroundings.

4.96 out of 5 average rating, 296 reviews

Country Cheese Factory - King Bed!

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Other great vacation rentals in Sheboygan

An arcade game console features classic gaming graphics and controls. Two wooden stools are positioned beside the console, providing seating. Soft carpet underfoot adds comfort to the playful space, while a light-colored chair is seen in the background.

4.96 out of 5 average rating, 171 reviews

The 2400 sq ft Plymouth Paddock 1 hour to Lambeau

Two white Adirondack chairs are positioned on sandy grass overlooking a calm lake. The distant view features a lighthouse with a red light, while a sailboat is seen gliding smoothly on the water under a clear blue sky.

4.96 out of 5 average rating, 181 reviews

Logan's Guest Nest

4.91 out of 5 average rating, 321 reviews

A wooden deck provides a serene view of the sandy beach and calm lake waters. Adirondack chairs face the shoreline, with natural boulders surrounding the water's edge. Lush greenery is visible along the side, complementing the open blue sky above.

Guesthouse in Oostburg

Beach House

A paddleboard rests on the sandy shore, facing a calm lake with gentle waves. The water reflects the soft blue hues of the sky, while clouds create a serene backdrop. Sunlight filters through, enhancing the tranquil setting.

4.77 out of 5 average rating, 13 reviews

3 Bedroom Beach House

A sandy beach stretches along the shore of Lake Michigan, with footprints leading towards the water. A cottage is visible in the background, complemented by wooden stairs that ascend from the rocks. The scene is framed by trees that line the edge of the beach.

5 out of 5 average rating, 11 reviews

SurfDaze! A Lake Michigan property

4.5 out of 5 average rating, 12 reviews

The dining area features a rectangular wooden table surrounded by six chairs, creating an inviting space for meals. A large window allows natural light to brighten the room. The kitchen, visible in the background, is equipped with modern appliances, enhancing functionality.

Apartment in Sheboygan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

A spacious deck is visible with a wooden table and benches, providing a comfortable outdoor space. Surrounding trees and lush greenery create a serene backdrop, while a clear blue sky filled with clouds enhances the inviting atmosphere.

4.95 out of 5 average rating, 42 reviews

Wander Back Inn to Sheboygan