Vacation rentals in Sheboygan

Apartment in Ellis Historic

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, 170 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!

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

4.98 out of 5 average rating, 202 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!

A stylish powder room features dark walls illuminated by modern wall sconces. A round mirror is placed above a sleek marble sink with brass fixtures. A towel hangs from a stylish ring, and a small plant adds a touch of greenery to the elegant space.

4.95 out of 5 average rating, 121 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Gentle sand dunes are seen, adorned with tufts of green grass against a clear blue sky. The expansive view of Lake Michigan stretches into the horizon, with calm waters reflecting the sunlight.

5 out of 5 average rating, 214 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

4.98 out of 5 average rating, 148 reviews

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.

Apartment in Sheboygan

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, 189 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.

Apartment in Ellis Historic

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, 501 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.

The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.

4.94 out of 5 average rating, 199 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.

Apartment in Downtown Sheboygan

4.84 out of 5 average rating, 225 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

Guesthouse in North Point

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.

4.82 out of 5 average rating, 460 reviews

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!

4.9 out of 5 average rating, 134 reviews

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. Send me a message to find out about our other available listings.

Vacation rentals for every style

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Popular amenities for Sheboygan vacation rentals

Self check-in

Pet friendly

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Laptop-friendly workspace

Pool

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, 470 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, 130 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

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, 71 reviews

Downtown Elkhart Lake - The Quintessential Suite

4.89 out of 5 average rating, 65 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

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

A contemporary living area features a brown leather couch paired with green and gray cushions. A circular mirror is set above a wooden coffee table adorned with a small potted plant. The space includes hanging greenery and a soft area rug, enhancing a calm ambiance.

4.98 out of 5 average rating, 41 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

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

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 Ellis Historic

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

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—-

Apartment in Ellis Historic

A cozy living area features a terracotta sofa facing a flat-screen television. Natural light fills the room through a large window, complemented by light blue curtains. A small blue coffee table sits on a soft area rug, while a wooden chair and door add to the inviting space.

4.8 out of 5 average rating, 20 reviews

Harbor View KING 2BDR Suite

5 out of 5 average rating, 42 reviews

A spacious living area features a comfortable navy blue sectional sofa, complemented by two cushioned chairs. A wooden coffee table sits at the center, while artwork adorns the walls. Soft lighting from multiple chandeliers creates a welcoming environment.

Home in North Point

Sheboygan's Great Lake's House

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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

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

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

Hotel room in 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.

New place to stay

1st Floor Double Suite Courtyard View