Vacation rentals in Sheboygan Falls

A deck area features white railings and two light blue Adirondack chairs, positioned for relaxation. A patterned outdoor rug is laid beneath, providing a comfortable foundation. Lush greenery and trees are visible in the background, offering a tranquil view of the surrounding landscape.

4.97 out of 5 average rating, 115 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!

4.95 out of 5 average rating, 267 reviews

A well-maintained lawn features lush green grass and shaded areas created by several mature trees. A glimpse of Lake Michigan is visible beyond the road, with a swing set adding a playful touch to the serene outdoor space.

Home in Two Rivers

Beach Haven, on Lake Michigan.

Incredible view of Lake Michigan from every room. Public beach across the street. No other place like this. Spectacular sunrises. Spacious living room and dining room, smart TV, kitchen and half bath on first floor. Three bedrooms and full bath on second floor. Pinball machine and music collection in basement. Bike paths, quaint downtown, restaurants within blocks. Easy drive to Lambeau Field, Whistling Straights, and Door County. Awaken to the sound of surf and gulls. Relax at Beach Haven.

5 out of 5 average rating, 19 reviews

Fairway Getaway

Welcome to our exquisite listing in Sheboygan, WI! This stunning property combines luxury, comfort, and amazing proximity to world class golf. Play a practice round on a state of the art Golf Simulator, Relax in the zen den, shuffle up and deal in the poker room, or have a movie night with family or friends on the big screen! Located near the renowned Kohler Spa, Whistling Straits, and other prestigious golf courses, this property is a haven for golf enthusiasts or a great space for Families

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

A comfortable wicker chair is positioned on a wooden deck, overlooking expansive views of the lake and sandy dunes. The deck features a railing that complements the outdoor setting, while the sky displays varied shades of gray and blue.

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

3 BR. 3 BA. Fully furnished. Granite counters and stainless steel appliances in large kitchen overlooking the lake. King and Queen suites with 2nd King and full Bath. Sleeps 6, but very large sofa. Washer/Dryer. Lake Michigan views throughout, Pool table room, work space, 2 levels of patios. Sits on landscaped sand dunes and beach. 10 min drive to Black Wolf Run Golf and resort. Front row for boat races from 2 decks. Den with large fireplace. Dining table overlooking lake + lighthouse.

5 out of 5 average rating, 36 reviews

Home in Oshkosh

WolfDen Getaway - Winnebago Channel

5/5 Rating on another travel site (55 Reviews) - "The Wolf Den is by far the best home our family has rented..." - 6/29/2023 You’re only a 1/4 mile from the boat launch. The channel allows you to dock your boat at the property during your stay. It’s a large home with plenty of space with a newly renovated lower level, including a pool table, ping pong, darts and foosball. Smart TVs in all the right places. 4 bedrooms/3 bathrooms. Plenty of parking. Brand new queen size murphy bed.

4.98 out of 5 average rating, 196 reviews

A game room is highlighted by retro arcade games and vibrant wall graphics. Bright colored arcade machines, including a shuffleboard and skee ball, stand out against a dark, playful backdrop. Warm lighting enhances the inviting atmosphere for entertainment and socializing.

Home in Oostburg

River Ridge-HOT TUB, Games, Luxury-10 bed, 5 STARS

The search is over, you have found the PERFECT getaway at River Ridge South! The moment you pull in, you will become instant hero for planning the ultimate retreat. This property has something for everyone! Beautiful seclusive country home (3800 sq ft) on 4 acres of a pristine and manicured lawn with the Onion River passing through it. This home is THE perfect countryside retreat for large group gatherings with three levels of finished space and great outdoor amenities.

4.97 out of 5 average rating, 144 reviews

Condo in Sheboygan

Downtown Beachside Condo with Lake Michigan Views

You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals. A deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art, & exquisite restaurants - walkable from the condo.

4.96 out of 5 average rating, 187 reviews

A hammock is set between two trees on a grassy area, facing the serene view of Lake Michigan. A spacious guest home with large windows is visible in the background, framed by lush greenery and a clear blue sky.

Home in Oostburg

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

4.99 out of 5 average rating, 282 reviews

An outdoor seating area features a hanging chair and a cozy couch, facing a fire pit with flames visible. The setting transitions from warm sunset hues to deep blue in the sky, while the calm waters of Lake Winnebago reflect the evening light.

Cottage in Fond du Lac

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

4.96 out of 5 average rating, 23 reviews

Villa in Sheboygan

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for families or groups. Enjoy a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. With 7 beds, a fully stocked kitchen, in-unit washer/dryer, and stylish living spaces, comfort and convenience come standard. Your relaxing lakeside getaway starts here.