Vacation rentals in Sheboygan

The exterior of a two-story brick duplex is displayed, featuring symmetrical windows and a welcoming front porch adorned with an American flag. A well-kept lawn surrounds the house, with blooming flowers and neat landscaping. Soft evening light enhances the home’s inviting presence.

4.98 out of 5 average rating, 167 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

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, 262 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!

5 out of 5 average rating, 123 reviews

Apartment in Kohler

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

A sophisticated living area features rich wood paneling and a plush carpet. Two green upholstered chairs are positioned beside a round coffee table with decorative accents. A large mirror reflects the space, while a bookcase filled with various books and decor items adds character to the room.

4.97 out of 5 average rating, 209 reviews

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

4.98 out of 5 average rating, 200 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully landscaped and decorated boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with Stearns and Foster King size bed. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

4.71 out of 5 average rating, 105 reviews

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

A round wooden dining table is surrounded by four white chairs, set against a light grey carpet featuring a geometric pattern. A bowl of yellow fruit sits in the center of the table. Natural light streams in from the adjoining area, enhancing the neutral tones of the space.

4.98 out of 5 average rating, 145 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

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, 186 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

A sandy beach is set against a clear blue sky, with gentle waves lapping at the shore. Lush green grass borders the beach area, while several volleyball nets are positioned on the sand, indicating recreational opportunities nearby.

4.93 out of 5 average rating, 499 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

4.96 out of 5 average rating, 129 reviews

Good VIBES On the Third COAST- Pets Welcome

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

4.84 out of 5 average rating, 223 reviews

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

4.82 out of 5 average rating, 460 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, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Vacation rentals for every style

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Spaces that are more than just a place to sleep

Popular amenities for Sheboygan vacation rentals

Self check-in

Pet friendly

Laptop-friendly workspace

Pool

Monthly stays

Family friendly vacation rentals in Sheboygan

4.98 out of 5 average rating, 279 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

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

4.94 out of 5 average rating, 469 reviews

A charming guest house exterior is framed by manicured landscaping. The entrance is highlighted by large wooden doors, with a welcoming porch illuminated by soft lighting. A one-car garage is present on the side, and lush trees provide a natural backdrop.

Home in Plymouth

Country Guest House - Beautiful Gardens!

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, 128 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

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

4.94 out of 5 average rating, 199 reviews

Beachfront getaway in Sheboygan

Apartment in Elkhart Lake

The modern kitchen showcases rich wooden cabinetry and a large island with granite countertops. A dining table is conveniently set for four, and eight chairs are positioned at the island. Warm lighting from pendant fixtures creates an inviting space, complemented by natural wood flooring.

4.99 out of 5 average rating, 70 reviews

Downtown Elkhart Lake - The Quintessential Suite

4.96 out of 5 average rating, 187 reviews

A spacious guest home is set against a backdrop of tall trees, positioned near a sandy beach. The exterior features a covered porch and two lounge chairs, inviting relaxation while enjoying the serene landscape.

Home in Oostburg

Shamba on the Lake, Oostburg, WI

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Dog friendly vacation rentals in Sheboygan

The main living area features a mix of seating options, including a modular sectional sofa and lounge chairs. A decorative area rug sits under a circular coffee table, while large windows offer views of the surrounding greenery. A fireplace enhances the inviting ambiance.

5 out of 5 average rating, 20 reviews

Norwind Ranch - Peaceful Retreat Near Road America

4.97 out of 5 average rating, 101 reviews

The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.

Chalet in Campbellsport

Long Lake Chalet

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

4.96 out of 5 average rating, 82 reviews

House Near the Lake

4.93 out of 5 average rating, 43 reviews

A well-lit bedroom features a queen-size bed with a patterned blue and white duvet, complemented by neatly arranged towels. A nightstand with a bedside lamp stands beside the bed, and natural light enters through a window dressed with blue curtains.

Condo in Sheboygan

Ellis District Urban Lake Condo

Place to stay in Elkhart Lake

A tree-lined pathway leads to a cozy cottage, framed by colorful fall foliage. Orange pumpkins are placed near vibrant purple flowers, enhancing the seasonal charm. The yard is spacious, surrounded by mature trees, providing a serene and inviting atmosphere.

4.96 out of 5 average rating, 227 reviews

Cottage @ Schoolhouse*Firepit*Petfriendly

A serene beach scene features two dogs running along the shoreline, their shadows stretching across the wet sand. The calm waves reflect sunlight, creating a shimmering effect on the water. A clear sky complements the tranquil setting.

4.89 out of 5 average rating, 97 reviews

The Beach | Sheboygan 2Br/1 Ba

4.94 out of 5 average rating, 100 reviews

A calm pond reflects the surrounding trees and buildings under a clear blue sky. The landscape showcases a blend of greenery and structures, creating a serene atmosphere. The still water enhances the tranquility of the countryside setting.

Farm stay in Oostburg

Blue Barn on the Green and Farmhouse Retreat

4.91 out of 5 average rating, 240 reviews

A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.

Home in Elkhart Lake

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

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Vacation rentals with pools in Sheboygan

A spacious room features two queen beds dressed in light-colored bedding. A wooden dresser and a desk are positioned against the wall, with natural light entering through sliding glass doors leading to a balcony. A ceiling fan adds comfort to the ambiance.

Apartment in Elkhart Lake

4.63 out of 5 average rating, 19 reviews

Siebkens Lockout Unit

4.88 out of 5 average rating, 8 reviews

An indoor pool area features a clear water pool surrounded by a tiled border. A large screen is positioned for viewing, and sunlight streams through two windows, illuminating the space. Colorful pool toys and two lounge chairs add comfort and convenience.

Home in Newton

Country Cottage Indoor Pool HOT TUB NFL Draft ava

4.97 out of 5 average rating, 33 reviews

The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.

Home in Plymouth

Private Home 4 BR+2Ba, Heated Pool by Road America

Hotel room in Elkhart Lake

An indoor pool area is surrounded by wood-paneled walls and expansive windows, allowing natural light to fill the space. Several blue chairs are positioned around the pool, and potted plants add a touch of greenery to the inviting setting.

5 out of 5 average rating, 5 reviews

Resort Life 2 Queen Suite

Apartment in Elkhart Lake

A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.

5 out of 5 average rating, 8 reviews

Resort Condo on Elkhart Lake

An inviting studio space features a spacious bed with a textured coverlet and a ceiling fan overhead. A kitchenette is visible, equipped with modern appliances and dark cabinetry. A dining table with light-colored chairs complements a cozy seating area, enhancing the overall functionality of the room.

Condo in Elkhart Lake

New place to stay

1st Floor Double Suite Courtyard View