Holiday rentals with lake access 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, 266 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!

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4.97 out of 5 average rating, 338 reviews

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.

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4.95 out of 5 average rating, 130 reviews

A spacious living area features a dark leather sectional sofa with colorful throw pillows. A textured ottoman sits in front, while natural light streams through large windows, illuminating the warm brick wall and wooden furniture. A decorative coffee table holds books and a candle.

Loft in Sheboygan

Spacious/stylish, 2br loft

Beautiful, spacious loft in active downtown. Washer/dryer, full kitchen, 1.5 baths, 2 Qu, 2 Tw, space for family/friends. Stocked w/home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. Bakery & fitness studio on 1st floor. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front near-by. Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

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A cozy living room is presented with floral wallpaper and natural light from a large window. Soft couches adorned with decorative pillows are complemented by armchairs. A dark wood coffee table occupies the center, while a floor lamp and side table add functionality and warmth.

4.85 out of 5 average rating, 109 reviews

The Garden | Sheboygan 2 Br/1Ba, Pet Friendly

Welcome to the Garden, a floral retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Garden is the perfect place to center your visit to Eastern Wisconsin. The Garden is a pet friendly apartment on the second floor of a duplex with 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. Easy check out with no to-do lists. Just pack and go! *new cleaning staff hired Jan’23*

NearbyOutdoor spacesLong stay

4.92 out of 5 average rating, 420 reviews

A serene lakeshore scene is captured at sunset, with the sun dipping below the horizon, casting warm hues across the sky. Gentle waves are visible in the foreground, while smooth stones line the water's edge.

Guest house in Oostburg

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

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The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

4.96 out of 5 average rating, 143 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!

Outdoor spacesNearbyQuiet

4.97 out of 5 average rating, 109 reviews

Cabin in Elkhart Lake

Fernwood Elkhart Lakefront: hot tub, pier, kayaks

Beautiful, serene lakehome on pristine Elkhart Lake. The hot tub, deck, screen porch & stone patio all have gorgeous lake views. The private pier is perfect for a dip, paddling or lounging by the water before basking in a luxurious sunset soak in the hot tub. Enjoy a stroll into the adorable town of Elkhart via the rustic lakefront path. With a chef’s kitchen and extensive amenities, it's perfect for a weekend or extended stay year round! We strive to be inclusive and welcoming 🏳️‍⚧️BLM🏳️‍🌈

Outdoor spacesViewLayout

4.96 out of 5 average rating, 183 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

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 a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Outdoor spacesNearbyQuiet

A modern kitchen and dining area are shown, featuring a white island with bar stools and a wooden dining table. Pendant lights hang above the island, while a stainless steel refrigerator and stove are visible in the background, complemented by a patterned backsplash.

4.96 out of 5 average rating, 147 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.

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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, 221 reviews

Stylish Getaway | Cozy Vibes | Perfect Girls Trip

Escape to a cozy, stylish retreat designed for relaxing weekends, girls trips, or family getaways. Start your morning with a sunrise and coffee on the patio looking out onto Lake Michigan, then spend the day exploring, and unwind at night around the firepit with a glass of wine. This home has everything you need for gathering and cooking together or cozying up to the fireplace and playing board games. A short walk to town, close to golf, breweries, winery, and a state park.

NearbyOutdoor spacesBeach

4.88 out of 5 average rating, 217 reviews

A view from the open door showcases a spacious deck leading to a grassy area with trees. Beyond the greenery, the blue waters of Lake Michigan are visible, capturing a serene outdoor scene.

Apartment in Sheboygan

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Outdoor spacesNearbyCondition

4.96 out of 5 average rating, 162 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Guest Favorite | Super Host + Clean & Modern Stay!

Unwind in this modern retreat just minutes from Whistling Straits Golf, Road America, Lake Michigan, and year-round outdoor adventures. The bright, open living spaces feature high ceilings, skylights, and stylish furnishings, with thoughtful comforts like heated bathroom floors. Enjoy the spacious outdoor living area for relaxing after a day out. Ideal for golfers, couples, families, wedding groups, business travelers, and traveling nurses.

Outdoor spacesNearbyCondition

Popular amenities for lake access rentals in Sheboygan

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

4.96 out of 5 average rating, 214 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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5.0 out of 5 average rating, 21 reviews

Luxury Villa on Lake Michigan!

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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.

5.0 out of 5 average rating, 87 reviews

Sheboygan's Great Lakes House

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5.0 out of 5 average rating, 22 reviews

Eve’s Place by beach 2 kings 1 queen + Pack’n Play

Outdoor spacesNearbyBathroom

5.0 out of 5 average rating, 49 reviews

Family Cottage, Walk to the lake (pet friendly)

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The spacious living area showcases a modern design, featuring a wooden accent wall and cozy seating arrangements. Large windows are adorned with cheerful yellow curtains, allowing natural light to brighten the room. Colorful artwork adds visual interest, complemented by a contemporary fireplace.

4.98 out of 5 average rating, 42 reviews

Beachside, Chefs Kitchen, High-End Everything

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5.0 out of 5 average rating, 49 reviews

A wooden deck equipped with a large dining table surrounded by six matching chairs faces the serene expanse of Lake Michigan. An umbrella is positioned to provide shade, and the bright blue sky enhances the view of the calm water.

Home in Oostburg

Lakefront Blue Dune Cottage on Lake Michigan.

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The exterior of the house features a modern design with a combination of white siding and grey shingles. A welcoming porch is enhanced by decorative blue chairs and flowering plants, providing a cozy entrance. A clear driveway leads to the side of the property.

5.0 out of 5 average rating, 26 reviews

Luxury 4B-2Ba Lake & Beach House

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Apartment rentals with lake access

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.

5.0 out of 5 average rating, 102 reviews

Recombobulation Station-In The Heart of Sheboygan!

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4.99 out of 5 average rating, 71 reviews

A Wave From It All! - Lake Condo

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4.96 out of 5 average rating, 25 reviews

Overlook Oasis | Coastal Haven in Ellis District

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A spacious living area is illuminated by natural light from two windows. A large, gray sectional sofa is accented by colorful cushions, and a round coffee table sits atop a soft area rug. A flat-screen TV is positioned on a media console, and decorative plants enhance the ambiance.

4.88 out of 5 average rating, 77 reviews

Sleeps 8 & Spacious!

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4.99 out of 5 average rating, 84 reviews

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.

Flat in Elkhart Lake

Downtown Elkhart Lake - The Quintessential Suite

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4.8 out of 5 average rating, 5 reviews

South Pier Condo! Best location in Sheboygan!

GrillHospitalityValue

5.0 out of 5 average rating, 12 reviews

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.

Flat in Elkhart Lake

Resort Condo on Elkhart Lake

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New place to stay

Malibu of the Midwest - Condo near Lake Michigan!

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Lake access cottage rentals

4.86 out of 5 average rating, 114 reviews

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

Private 3 bedroom lake house

NearbyOutdoor spacesLocation

4.96 out of 5 average rating, 56 reviews

Cottage in Oostburg

1 week in August is open and the water is warm!

Outdoor spacesNearbyFamily

4.86 out of 5 average rating, 28 reviews

The exterior of the lake house showcases natural stone and wooden elements, surrounded by lush greenery. A spacious deck overlooks Forest Lake, with a private dock extending into the water. Cozy seating arrangements are visible around a fire pit, creating inviting outdoor spaces.

Cottage in Campbellsport

Forest Lake Getaway

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5.0 out of 5 average rating, 45 reviews

Cottage in Elkhart Lake

Villa von Baumbach - Trade Screens for Stories

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4.96 out of 5 average rating, 23 reviews

A view of Wolf Lake is presented through large windows, featuring a comfortable seating area with a textured blanket. An umbrella shelters the outdoor deck, indicative of a relaxing lakeside setting. Lush greenery and the water create a serene backdrop.

Cottage in St. Cloud

Lakefront Cottage - June Weekends and EAA dates!

Outdoor spacesViewBathroom

An outdoor seating area features a large rectangular table surrounded by multiple chairs. An umbrella provides shade over the dining space, with lush greenery and a clear view of the lake in the background, enhancing the tranquil atmosphere.

Cottage in Random Lake

4.75 out of 5 average rating, 16 reviews

Lakeside Haven | New Deck, Pier & Guest House

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