Holiday houses in Sheboygan

4.91 out of 5 average rating, 236 reviews

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

MelissaRating, 5 stars3 days ago

Our visit was great. We decided on a last minute weekend getaway and chose the right spot. My husband and I enjoyed our air hockey and pinball tournaments along with a hot tub soak at night. Lots of great movies to pick from and a great yard our lab enjoyed. Even though there are neighbors nearby, it felt very private and quiet. Would definitely return :)

Apartment in Port Washington

4.91 out of 5 average rating, 139 reviews

Lighthouse View -a real gem on Sweet Cake Hill

JohnRating, 5 stars1 week ago

Great hosts with a nice apartment, It was everything I remember about living in Port Washington. The older apartment made us feel right at home. Easy to find and within walking distance of downtown Port Washington. Thank you for providing our place to stay

4.96 out of 5 average rating, 155 reviews

Lake Michigan Beach Home by Frank Lloyd Wright pro

LoriRating, 5 stars1 month ago

Was a very relaxing week, even with the stormy weather, high winds and cold temps. A true Gem of a home, thanks so much for sharing Hal. The views are incredible, watching the waves is mesmerizing. Comfortable bed and furniture. I read, painted, drew and lounged all by myself and loved it. Would definitely recommend and would love to come back.

4.98 out of 5 average rating, 196 reviews

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

JeremyRating, 5 stars4 days 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!

4.94 out of 5 average rating, 196 reviews

Home in Sheboygan

Beachfront getaway in Sheboygan

Laura KRating, 5 stars3 weeks 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.

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars1 week 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.

4.96 out of 5 average rating, 23 reviews

Villa in Sheboygan

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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What guests are saying

A Glorious Getaway Sheboygan - LUX Lake Condo

4.98 out of 5 average rating, 41 reviews1 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.

Condo in Sheboygan

What guests are saying

Unmatched Location, Views, & Style. Welcome Home!

5 out of 5 average rating, 31 reviews1 week ago

This spacious and sublimely decorated, well-appointed, flat with gorgeous views of the Sheboygan River and Lake Michigan is immaculate, and each bedroom and bath is stocked with extra pillows, blankets, and fluffy towels. The furniture is comfortable, seems relatively new, and is not worn. Because we were due to arrive late on a very chilly night after a long flight and drive, I messaged Jill the morning of our scheduled arrival to let her know, and she made sure the place was heated and well lit when we arrived. There's very little for guests to do when checking out -Jill and crew make it easy.

Home in Sheboygan

What guests are saying

3-bdrm beachfront home on Lake Mich, Sheboygan WI

4.94 out of 5 average rating, 51 reviews6 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!

Home in Sheboygan

What guests are saying

Heavenly Condo in the Malibu of the Midwest

4.97 out of 5 average rating, 31 reviews2 months ago

Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.

Condo in Sheboygan

What guests are saying

State Park w/ Orchard Style Yard & Pavilion

4.96 out of 5 average rating, 25 reviews7 months ago

We had a great stay at The Orchard House Retreat. The property is as described, looks like the pictures and had everything we needed. The kids especially loved all the toys and books! The house is 5 min to the State Park beach and 10 min from downtown. We loved having the backyard, the furniture was well taken care of and the fire pit was perfect for s’mores. The hosts were very responsive and accommodating— with everything labeled around the home. It’s also a great layout for bigger families /groups with 2 bedrooms upstairs, 1 on the main floor and 1 in the basement.

Home in Sheboygan

What guests are saying

Janelle's Dockside Condo

4.93 out of 5 average rating, 86 reviews2 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!

Condo in Sheboygan

What guests are saying

Spacious/stylish, 2br loft

4.98 out of 5 average rating, 96 reviews4 days ago

This was the perfect stay! Cynthia’s place is absolutely amazing—just as described. It’s a spacious, beautifully appointed loft in a great part of town. We were in town for an event at the John Michael Kohler Art Center, and everything planned for the weekend was just a few blocks away. We loved being able to walk everywhere and come home to such a gorgeous and comfortable space. Highly recommend!

Loft in Sheboygan

What guests are saying

Above Garage Apartment w/ Private Beach

4.94 out of 5 average rating, 54 reviews6 months ago

Dustin was a welcoming, kind host. He gave us the option of letting ourselves in or ringing the doorbell to meet him. We decided to meet him and had great conversation. We loved that he took the time to get to know us, even though he has a busy family. If we didn’t want to, we easily could have just walked up the stairs to the apartment with no contact, but meeting him made it more personal and memorable. Other notes: Dustin was very responsive and proactive. Prior to arrival, he messaged us, warning that there’s a dog (Stella) who would probably bark at us upon arrival. Indeed, she was there but was as sweet as can be and loved alllll the belly rubs. We had a busy weekend in the area, but we took a little time to explore the beautiful property. The apartment was just perfect and the best thing was that we didn’t have to do anything for checkout, except pack up our own things. We hope to visit again when we are up in that area in the future. Thank you, Dustin!

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Stay near Sheboygan's top sights

John Michael Kohler Arts Center60 locals recommend

Il Ritrovo53 locals recommend

Trattoria Stefano44 locals recommend

Field to Fork44 locals recommend

Blackwolf Run Golf Course43 locals recommend

3 Sheeps Brewing Company42 locals recommend

Other great holiday rentals in Sheboygan

4.96 out of 5 average rating, 171 reviews

Home in Plymouth

The 2400 sq ft Plymouth Paddock 1 hour to Lambeau

JuliaRating, 5 stars4 days ago

Can’t say enough positive things! Perfect place for families - plenty of space, well stocked, even has all the kids toys and great amount of beds / bedroom space.

Superhost

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) :)

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!

4.98 out of 5 average rating, 125 reviews

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

DavidRating, 5 stars6 months ago

This place is suitable for a small family or a few adults. Very clean and well thought-out amenities made it quite attractive. Because we were very busy at Road America every day, we did not have an opportunity to use the kitchen except to make coffee, but had we wanted to cook, I'm sure we would have found everything needed. The only "warning" is that anyone with some mobility issues might find the stairway to the second floor a bit daunting. If we need a place in the area again, we would likely choose this house again.

Superhost

Apartment in Sheboygan

4.5 out of 5 average rating, 12 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Christian DavidRating, 5 stars9 months ago

Excellent place, I was there for almost 2 months and is very peaceful, the place is exactly like photos, everything was great, Thank you Chris

4.95 out of 5 average rating, 42 reviews

Home in Sheboygan

Wander Back Inn to Sheboygan

LaurieRating, 5 stars1 month ago

We had a great time at this place. Everything was as described. Very easy to work with and accommodating.

4.99 out of 5 average rating, 163 reviews

Loft in Port Washington

Cozy Carriage House Loft – Walk to Lake & Downtown

Cathipt@Yahoo.ComRating, 5 stars5 months ago

Missy and Bret were great hosts and the treats of muffins, coffee, and drinks in the refrigerator were appreciated. This is a lovely place and a great get away. The only concern was that I misunderstood that there is only one queen bed in the bedroom. There is a second queen size pull out in the couch. The beds were comfortable and the movies, music and games are a nice addition.