Apartment holiday rentals in Sheboygan

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

4.98 out of 5 average rating, 209 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!

An open living space features a round dining table with four chairs, complemented by a cozy seating area with a sofa adorned in warm tones. Natural light filters through large windows, while string lights add a gentle illumination to the ceiling.

4.93 out of 5 average rating, 40 reviews

Parkside Studio Apartment

Escape to this peaceful family retreat next to a wooded park! Just 2 mins. from Lake Michigan, 5 mins. from Kohler-Andrae State Park, and 10 mins. from the harbor, our spacious, newly remodeled studio offers the perfect getaway. It's ideal for families with a king bed, bunk bed, and pullout queen sofa. Enjoy free Wi-Fi, Smart TV, a dedicated workspace, and hassle-free parking. Whether exploring the outdoors or simply unwinding, this cozy haven has all the comforts you need for a memorable stay!

A renovated historic home displays a charming exterior with wide steps leading to a wooden front door. Flanking the entrance, tall evergreen trees create a natural boundary. The building features multiple large windows, enhancing its traditional architectural style.

4.95 out of 5 average rating, 88 reviews

Quaint Blast from the Past - walk to lake/8th st

Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!

4.97 out of 5 average rating, 142 reviews

A wooden table displays a variety of items: an open book, a lime, a glass filled with dark liquid, and a bottle of rum beside a vintage Coca-Cola. A bouquet of vibrant flowers sits neatly in the background, with light filtering through a window.

Flat 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 cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.

4.9 out of 5 average rating, 110 reviews

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

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.

4.98 out of 5 average rating, 182 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.

The bedroom features a spacious bed adorned with cotton linens, complemented by decorative pillows. Nightstands with lamps are placed on either side. A small television is mounted on the wall, while a white dresser provides additional storage. Light-colored flooring enhances the airy feel.

5 out of 5 average rating, 54 reviews

The Sheboygan Foodie Flat

Schnazzy upper flat in the heart of Sheboygan’s Eastside. Walk to Lake Michigan Beaches, Riverfront, Uptown and Downtown. Enjoy the newly renovated 2nd floor of an 1893 historic rambler, with lots of natural light. -Desirable Eastside, with walkable neighborhoods. -Large Italian tile walk-in shower with Kohler fixtures. -Fully equipped kitchenette with microwave, convection oven, two-burner hot plate, Keurig, coffee pot & toaster. -New furnishings -Sheboygan Foodie Guidebook

A comfortable living area features a sectional sofa in a soft grey hue, a rustic wooden coffee table, and natural light streaming through large windows. Unique décor includes a vintage style chair and a wall-mounted shelf with plants and books.

4.93 out of 5 average rating, 538 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.

5 out of 5 average rating, 27 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

A spacious living room is equipped with a comfortable sofa and two armchairs. A TV screen is positioned adjacent to an original fireplace, which now houses an electric device. Natural light enters through a window, and a decorative area rug enhances the room's charm.

4.87 out of 5 average rating, 113 reviews

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

A comfortable living area features a plush sofa, a bean bag chair, and a modern television. A wooden dining table with three high stools is positioned in the center. Natural light flows in through large windows, enhancing the inviting space.

5 out of 5 average rating, 87 reviews

Recombobulation Station-Locally Owned Surf Escape

We love this town and we love hosting. If you need any local recommendations we have plenty! Blocks from North Beach+Riverfront+8th St Kitchen is stocked and ready for your cooking needs. Main Bedroom - Luxurious pillow top mattress + Blackout Blinds + Ceiling Fan 15min-Kohler Spa & Whistling Straits 20min-Road America 1hr-Green Bay/Lambeau Field Military Discount 🪖 🙏 Clean & Comfortable-Continuously maintained and updated.

4.98 out of 5 average rating, 287 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.

Flat in Waldo

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Popular amenities for Sheboygan apartment rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Weekly apartment rentals

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Flat in Plymouth

4.63 out of 5 average rating, 336 reviews

Pineyard Plymouth Apartment

Superhost

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.

4.62 out of 5 average rating, 21 reviews

Siebkens Lockout Unit

Superhost

A living room featuring a dark leather sofa, a cozy armchair, and a coffee table on a patterned rug. Natural light filters through double doors leading to a balcony, while two lamps provide additional lighting. Various framed pictures adorn the walls.

4.76 out of 5 average rating, 45 reviews

Bed & Beer -4 bdrm above a bar

4.9 out of 5 average rating, 10 reviews

A well-appointed bedroom features a spacious bed dressed in white linens. A quilted blanket is neatly placed at the foot of the bed. A gray patterned rug lies underfoot, complemented by a stylish bench and a light gray accent chair beside a window with light-filtering blinds.

Flat in Sheboygan Falls

Elegant Condo in Sheb Falls

5 out of 5 average rating, 7 reviews

Storybook Home - 1 mi to Lake & Downtown Sheboygan

5 out of 5 average rating, 5 reviews

A decorative wooden sign displays the phrase 'Knot A Care by the Lake' in bold black letters. The sign features a braided rope design at the center, enhancing the nautical theme. The background is a light-colored wood, providing a contrasting framework for the text.

Flat in North Point

Knot A Care By The Lake

The modern kitchen features sleek gray cabinetry and a spacious countertop. Essential appliances include a range, microwave hood, and refrigerator. A television is mounted on the wall for entertainment, and light is provided by recessed lighting in the ceiling.

4.5 out of 5 average rating, 22 reviews

Cozy and Modern Upper Near Lake

A spacious living room with large windows offers abundant natural light and views of the river and Lake Michigan. Two comfortable couches and a coffee table are arranged around a media console with a television. A ceiling fan provides circulation, and decor includes nautical accents.

4.62 out of 5 average rating, 21 reviews

Welcome to Harbor Nights!

Private apartment rentals

A serene bedroom features a queen-size bed with light-colored bedding, complemented by a plush rug. Natural light fills the room through three windows, creating a bright atmosphere. A patterned chair and a tall black storage unit complete the space, showcasing hardwood flooring throughout.

4.79 out of 5 average rating, 43 reviews

Prime central location-Tempurpedic

Flat in Campbellsport

4.95 out of 5 average rating, 40 reviews

'McJugger’s Loft:' Walk to Lake, Park, Restaurants

The exterior of a renovated farmhouse is displayed, showcasing light grey siding and a wooden deck adorned with potted plants. Ample greenery surrounds the property, and multiple windows reflect the surrounding natural light. A cozy seating area is visible on the deck, inviting relaxation.

5 out of 5 average rating, 63 reviews

Lime Ridge Guest House

A comfortable living area features a gray sofa adorned with patterned cushions. A small dark table sits in front, accompanied by a throw blanket draped casually. Natural light is filtered through sheer and dark curtains framing two windows.

4.91 out of 5 average rating, 22 reviews

Home away from home

A cozy room features an original brick wall, a queen-size sleep number bed, and a small dining area with a wooden table and chairs. A double whirlpool tub is positioned nearby, with a private bathroom visible. A flat-screen TV is mounted on the wall.

4.84 out of 5 average rating, 31 reviews

Helene's room

A residential property is shown with a welcoming exterior, surrounded by lush greenery and well-maintained landscaping. A large tree provides shade in the foreground, while a driveway leads to a two-car garage in the background. Soft light filters through the leaves, enhancing the serene atmosphere.

4.67 out of 5 average rating, 9 reviews

Sheboygan Getaway w/ Deck + On-Site Lake Access!

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, 11 reviews

Resort Condo on Elkhart Lake

4.94 out of 5 average rating, 18 reviews

A living area is showcased with a flat-screen TV mounted on a stand and a round dining table surrounded by wooden chairs. A cozy bedroom is visible in the background, and large windows allow natural light to illuminate the space.

Flat in Sheboygan Falls

Country Apartment

Family-friendly apartment rentals

A two-story farmhouse features a white exterior, complemented by a front porch with a railing. A neatly manicured lawn and flower beds surround the building. A vintage silver car is parked in the foreground, showcasing vibrant red accents on the wheels.

4.97 out of 5 average rating, 103 reviews

Elkhart getaway near downtown

Flat in Downtown Sheboygan

A leather sectional sofa is positioned beside a round coffee table, set on a textured area rug. A vintage surfboard is displayed above the couch, complementing the decor. A chair and lamp provide additional seating, while a small dresser holds a decorative lamp, enhancing the cozy ambiance.

4.91 out of 5 average rating, 150 reviews

Sheboygan Surf House - North Point

A fully equipped kitchen is featured, showcasing dark wooden cabinetry and stainless steel appliances. A round wooden dining table with four matching chairs is positioned nearby. Natural light filters through a window adorned with light curtains, illuminating the warm tones of the flooring.

4.85 out of 5 average rating, 88 reviews

Fully Loaded and Clean! King

4.99 out of 5 average rating, 81 reviews

A two-story brick building houses a coffee shop on the ground floor, featuring large windows flanked by a striped awning. The entrance is highlighted by a sign that announces it as Kettle Moraine's Favorite Espresso Bar. A welcoming atmosphere is created by its corner placement and outdoor seating area.

Flat in Kewaskum

Local Landmark CF / Coffeehouse / Kettle Moraine

A cozy living room is furnished with two patterned sofas and an armchair, arranged around a glass coffee table. Natural light filters through large windows adorned with blinds, illuminating the wooden floor and a decorative rug. A television is positioned near the entrance.

North side Sheboygan, great area

New place to stay

Newly updated efficiency - cozy & convenient.

Superhost

A light-filled living area features a comfortable orange sofa, a wooden coffee table, and a small plant. The dining area with a dark wooden table is visible, along with a kitchen equipped with white cabinetry and essential appliances. The flooring is a warm, rich tone.

4.71 out of 5 average rating, 28 reviews

Bird's View King Suite

A modern kitchen features sleek white cabinetry and a marble backsplash. Stainless steel appliances include a dishwasher and a gas range, complemented by a wooden range hood. A decorative area rug lies on the light wood flooring, enriching the overall design.