Vacation rentals in Sheboygan County

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Top-rated vacation rentals in Sheboygan County

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Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars6 months ago

Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

Guest favorite

Condo in Sheboygan

4.93 out of 5 average rating, 86 reviews

Janelle's Dockside Condo

ElaineRating, 5 stars3 weeks ago

We loved everything about this stay. Janelle has created a very beautiful space with absolutely everything we needed for a peaceful vacation. It is spacious and immaculately clean. The location is priceless. We had an easy walk to Lake Michigan, great restaurants, fun shops, and great coffee. We will definitely be back!

Top guest favorite

Condo in Sheboygan

4.98 out of 5 average rating, 41 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

JohnRating, 5 stars1 month ago

Susan was exceptionally responsive and inviting. She let us arrive early for our Mother's celebration of life weekend. It was easy to find once you figured out the address and unit numbers. Parking was ideal and plentiful. You can see the beach and lake from the walk out balcony.

Guest favorite

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

4.98 out of 5 average rating, 196 reviews

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

JeremyRating, 5 stars1 week ago

Our stay at River Ridge was just what we were looking for. A relaxing stay with extra amenities to keep the family occupied. This hours has everything you need to be comfortable and is kept in amazing condition. Communication with Tyler and his management team was very simple and always very quick. We thoroughly enjoyed our stay!

Guest favorite

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.

Home in Sheboygan

4.94 out of 5 average rating, 196 reviews

Beachfront getaway in Sheboygan

Laura KRating, 5 stars1 month ago

What a beautiful home! And a beautiful setting right on a sandy beach Lake Michigan. Plenty of board games and puzzles and music to listen to in the house. And we enjoyed trying local restaurants, all close by, and drove up to the dunes Park which was otherworldly and a short drive from the house.

Top guest favorite

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

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars2 weeks ago

We have stayed at Shamba 4 times. It is an absolutely amazing spot on Lake Michigan. The home is lovely and very spacious. You could not ask for better views of the lake from inside or outside. The beach is literally right outside your door. Great spot for kids to play and great for walks too. Will definitely return again.

Guest favorite

A charming two-story condominium features a well-maintained exterior with white siding and blue accents. Large balconies are situated on the front, supported by stone columns. A landscaped pathway leads to the entrance, and manicured grass surrounds the building, enhancing the inviting atmosphere.

Villa in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

MikeRating, 5 stars6 months ago

Great host!! Great location!! Great property!! We came in town for a golf trip and this property was a perfect location and comfortable. Nice to start each morning with a quick walk to the beach and watch the sun rise over the lake. Would definitely stay here again and would recommend it to anyone looking to stay in the area.

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Popular amenities for Sheboygan County vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Sheboygan County

A serene lakeside view features a wooden dock extending into crystal clear water, accommodating a small boat. Surrounding trees provide natural shade. A stone path leads to picnic tables set on the shore, inviting outdoor gatherings.

Home in Plymouth

4.92 out of 5 average rating, 13 reviews

the getaway at crystal lake!

MikeRating, 5 stars44 months ago

This is a warm, inviting home with a terrific location in the lake. Jana and Josh’s house was very comfortable, clean, spacious and stocked with everything we needed for our vacation. An absolutely beautiful spot on the lake. Jana and Josh were extremely helpful and generous hosts who really anticipate what guests may need. We loved our stay!

Superhost

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

4.84 out of 5 average rating, 67 reviews

Private 3 bedroom lake house

HoaRating, 5 stars2 weeks ago

Awesome place. We will be back!

Condo in Sheboygan

5 out of 5 average rating, 8 reviews

'Beautiful Day Getaway' - Lake Michigan Views

KathrynRating, 5 stars8 months ago

We loved our stay and can’t wait to be back. The house was perfect for our party of 8 and had tons of room for everyone as well as good communal space.

Guest favorite

A light-filled hallway features a sleek, neutral wall color and warm wooden flooring. A small shelf with decorative items is mounted on the wall, while a mirror on the opposite side enhances the sense of space. Doorways lead to the rooms beyond.

Apartment in Sheboygan

4.85 out of 5 average rating, 61 reviews

Fully Loaded and Clean! King

StevenRating, 5 stars2 months ago

Great stay in Sheboygan! So close to the harbor and downtown it was great! Highly recommend the Italian restaurant trattoria and the other 2 places associated w them. Our stay was a great place to hang out and relax as well as a base of operations for local adventures!

Guest favorite

A spacious backyard area is visible, featuring a fire pit surrounded by several outdoor seating options. The lush green lawn extends toward the tranquil waters of Random Lake, with trees lining the shoreline and a clear blue sky overhead.

Cottage in Random Lake

5 out of 5 average rating, 8 reviews

Cozy Lakefront Escape: Ideal Seasonal Getaway

CheyanneRating, 5 stars3 months ago

Such a beautiful and peaceful place. Host is very friendly and responsive. First time I’ve woken up feeling well rested in a minute, beds really helped any of our back issues. Main parking spots might not be available at first due to people parking there for ice fishing on the lake but plenty of street parking. If staying in the winter, run the water for a moment to run through any sediment in the pipes. (Not a house problem, just winter in Wisconsin.) :)

Superhost

A paddleboard rests on the sandy shore, facing a calm lake with gentle waves. The water reflects the soft blue hues of the sky, while clouds create a serene backdrop. Sunlight filters through, enhancing the tranquil setting.

Home in Sheboygan

4.77 out of 5 average rating, 13 reviews

3 Bedroom Beach House

KatieRating, 5 stars20 months ago

Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)

Top guest favorite

Home in Oostburg

5 out of 5 average rating, 11 reviews

SurfDaze! A Lake Michigan property

JosephRating, 5 stars1 month ago

We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!

Top guest favorite