Apartment vacation rentals in Sheboygan

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.

4.91 out of 5 average rating, 32 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!

Apartment 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, 148 reviews

Sheboygan Surf House - North Point

This super spacious studio apartment is the largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for beach days, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a large refrigerator and a gas range. Light granite countertops provide ample workspace, complemented by warm lighting from a stylish overhead fixture. The space is accentuated by a neutral-colored door leading to the entrance.

4.98 out of 5 average rating, 124 reviews

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment offers a true lower level living experience. You may notice some noise, including foot traffic, from your amazing upstairs Airbnb neighbors. But.. with all the great restaurants, golf, fishing, and the beach nearby you won’t even have the time to hear it! Located only 1 block from the beach on Lake Michigan - you’ll find relaxation and a great time here at the heart of Sheboygan’s Shoreline.

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, 109 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-appointed bedroom features a spacious bed with white linens and a textured gray throw. Two decorative lamps provide soft lighting on either side of the bed. Bright windows are framed by patterned curtains, and wall art adds a touch of elegance to the neutral-colored walls.

4.96 out of 5 average rating, 50 reviews

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

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, 179 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.

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, 530 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.

A light-filled living space is furnished with a comfortable blue sofa and armchair. A round coffee table sits atop a soft area rug, while a large TV is positioned on a wooden media console. Natural light filters through the window, complemented by a potted plant.

4.85 out of 5 average rating, 60 reviews

*NEW* Beautiful & Convenient!

Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally located, just 4 mins to downtown and 5 mins to the shoreline! Upon entry you are welcomed by a spacious living and dining area. Relax and unwind on new memory foam mattresses in all bedrooms! 43" Roku TVs in all bedrooms and 65" Roku TV in living area. Kitchen is fully stocked for meal preparation. Enjoy the coffee & tea bar! We are pet friendly!

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.

4.86 out of 5 average rating, 111 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.

4.98 out of 5 average rating, 286 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

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.

Apartment in Campbellsport

A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.

4.97 out of 5 average rating, 104 reviews

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

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.

Apartment in Plymouth

4.63 out of 5 average rating, 334 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

Apartment in New Holstein

A spacious room features a large bed positioned against a dark headboard. Soft lighting highlights the cozy seating area, which includes two armchairs. A medium-sized area rug is placed beneath the furniture, and natural light enters through two windows dressed with light curtains.

4.97 out of 5 average rating, 58 reviews

Parkside Retreat | Minutes from Elkhart Lake

Superhost

A well-lit living room features two black leather sofas and a futon, providing ample seating. A wooden coffee table sits centrally, with a lamp illuminating the space. Accent chairs complement the arrangement, and natural light enters through partially covered windows.

4.79 out of 5 average rating, 24 reviews

On Broadway

5 out of 5 average rating, 5 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.

Apartment in North Point

Knot A Care By The 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, 79 reviews

Downtown Elkhart Lake - The Quintessential Suite

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

A spacious indoor area features a dining table set for six with earthy dishware and a vase of sunflowers at the center. Cozy seating is provided by a brown leather couch and wooden chairs, with the open layout leading to a well-equipped kitchen.

Apartment 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 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!

Apartment in Sheboygan Falls

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.

4.89 out of 5 average rating, 9 reviews

Elegant Condo in Sheb Falls

Apartment in Sheboygan Falls

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.

4.94 out of 5 average rating, 18 reviews

Country Apartment

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

Family-friendly apartment rentals

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 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

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

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.

4.67 out of 5 average rating, 3 reviews

3 BR Lower-Brand New Remodel

The living area features two light-colored sofas arranged around a wooden coffee table. A TV is positioned on a nearby stand, while a patio door allows natural light to enter. A small round table with chairs is also visible against the wall.

Apartment in Plymouth

Centrally located apartment.

A charming two-story farm home is framed by lush greenery and well-maintained gardens. A spacious driveway leads to the entrance, showcasing a blend of colorful flowers and neatly trimmed hedges. The home's exterior features subtle blue siding and welcoming accents.

Apartment in Plymouth

4.82 out of 5 average rating, 11 reviews

Kettle Edge Retreat and Gardens

A two-story white farmhouse is viewed from a distance, set against a clear blue sky. Lush green grass surrounds the property, complemented by a flowering shrub near the entrance. A paved driveway leads up to the home, which features a welcoming front porch.