Vacation rentals in Sheboygan

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Popular amenities for Sheboygan vacation rentals

Family friendly vacation rentals in Sheboygan

Top guest favorite
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
4.98 out of 5 average rating, 279 reviews

The Blue Cobb House

MikeRating, 5 stars1 month ago
My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!
Guest favorite
An outdoor fire pit area is surrounded by vibrant red chairs arranged in a circle. The sun sets over Lake Michigan, casting a warm glow on the grassy landscape, which gently slopes towards the beach. Additional seating is visible nearby.
Home in Sheboygan
4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars7 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
A charming guest house exterior is framed by manicured landscaping. The entrance is highlighted by large wooden doors, with a welcoming porch illuminated by soft lighting. A one-car garage is present on the side, and lush trees provide a natural backdrop.
Home in Plymouth
4.94 out of 5 average rating, 469 reviews

Country Guest House - Beautiful Gardens!

JeffRating, 5 stars2 weeks ago
Looking for a place to stay when we visited our kids for the weekend. Lots of room for the dogs to run and played pool and air hockey. Great place!!
Guest favorite
A welcoming living area features two comfortable sofas adorned with striped cushions and a wooden coffee table in the center. Natural light enters through a window with sheer curtains, creating a bright and inviting space. Light-toned hardwood floors complete the room.
Home in New Holstein
4.86 out of 5 average rating, 139 reviews

Growe's Guest House - just like Grandma's!

Israel IzzyRating, 5 stars8 months ago
The place was clean, nice and good amenities. Mary was responsive to our questions and very helpful. We were there for the SCCA Championship races at Road America ! We Left at 7am and returned at 10pm everyday. We did enjoy it. We only wish the upstairs bathroom had a shower instead of a soaking tub. (Since 4 guys all trying to take a shower before rushing off to sleep. Very nice place.
Top guest favorite
The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.
Home in Glenbeulah
4.98 out of 5 average rating, 128 reviews

Stay at Sunrise LLC, Like being at Grandma's

ArleneRating, 5 stars1 week ago
Very friendly and welcoming hosts. The place was exceptionally clean and the kitchen was well stocked which enabled me to make a bunch of food to take to the kettle moraine state forest campground where we spent much of our free time with friends. The beds were comfortable and the home was well maintained with lots of welcoming details like bottled water in the fridge and snacks for us in the kitchen. I got the impression that everything was meticulously cared for which I really appreciated and as a result I was able to relax and enjoy my stay here.
Guest favorite
A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.
Home in Sheboygan
4.94 out of 5 average rating, 199 reviews

Beachfront getaway in Sheboygan

DanRating, 5 stars1 month ago
To find a place in the middle of Sheboygan and right on the beach was fantastic. We loved the location but everything about the house was really perfect. Easy, super clean, and comfortable in every way.
Top guest favorite
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.
Apartment in Elkhart Lake
4.99 out of 5 average rating, 70 reviews

Downtown Elkhart Lake - The Quintessential Suite

TanyaRating, 5 stars6 days ago
We absolutely love this place! Will definitely come back. The place is very comfortable; we felt right at home and had everything we needed for our stay. The hosts are very friendly and accommodating. Thank you Ryan!
Top guest favorite
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
4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

SandyRating, 5 stars1 month 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.

Dog friendly vacation rentals in Sheboygan

Top guest favorite
The main living area features a mix of seating options, including a modular sectional sofa and lounge chairs. A decorative area rug sits under a circular coffee table, while large windows offer views of the surrounding greenery. A fireplace enhances the inviting ambiance.
Home in Sheboygan
5 out of 5 average rating, 20 reviews

Norwind Ranch - Peaceful Retreat Near Road America

MichaelRating, 5 stars7 months ago
Flew in for business with Acuity Insurance. Perfect place to stay. Drove up to Green Bay for the Texans vs. Packers game. Only an hour drive from the house in Sheboygan. I will definitely stay here again when I come back to town!
Guest favorite
The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.
Chalet in Campbellsport
4.97 out of 5 average rating, 101 reviews

Long Lake Chalet

JacobRating, 5 stars1 week ago
The cabin itself was fantastic. Clean and accommodated our family of 6 including a pet well. The hosts were very responsive and helpful. The cabin was cozy and had great finishes. We enjoyed the fire pit and provided firewood. It was a fantastic tough having a fire going when we arrived. A couple of things to consider that are not necessarily in the owners control but helpful: the water off the dock is extremely weedy and not conducive to swimming or bobber fishing for kids. We are a tad disappointed in that. The lawn area was quite mushy given the lake was high so was practically unusable this time of year. Fishing was also pretty rough but likely due to high water and time of year. Again, time of year and not due to anything the owners can control for all the above. We enjoyed the two kayaks, canoe and paddle boat provided. The grill was a little banged up but got the job done. Overall the owners have a very well kept, cozy cabin that is very charming
Top guest favorite
A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.
Home in Sheboygan
4.96 out of 5 average rating, 82 reviews

House Near the Lake

BrianRating, 5 stars5 days ago
Loved the place. Felt right at home. Made sure that we had everything we needed and to reach out if there was a problem! Nice and quiet neighborhood. Highly recommend and can't wait to be back!
Top guest favorite
A well-lit bedroom features a queen-size bed with a patterned blue and white duvet, complemented by neatly arranged towels. A nightstand with a bedside lamp stands beside the bed, and natural light enters through a window dressed with blue curtains.
Condo in Sheboygan
4.93 out of 5 average rating, 43 reviews

Ellis District Urban Lake Condo

Sarah MarieRating, 5 stars3 weeks ago
Our stay was great! Very easy to check in and out. Easy to find, very clean. We came up to fish, only recommendations we would have as people fishing is a little more table room in the living room/rooms (ex. Coffee table, bigger/extra side table) and hooks for hanging clothes that need to dry maybe by the door. Again, our stay was amazing, would definitely stay again!
Guest favorite
A tree-lined pathway leads to a cozy cottage, framed by colorful fall foliage. Orange pumpkins are placed near vibrant purple flowers, enhancing the seasonal charm. The yard is spacious, surrounded by mature trees, providing a serene and inviting atmosphere.
Place to stay in Elkhart Lake
4.96 out of 5 average rating, 227 reviews

Cottage @ Schoolhouse*Firepit*Petfriendly

PattyRating, 5 stars1 week ago
What a lovely small house and location! I felt right at home and it was very convenient for my trip to Elkhart Lake and Road America. I only wish I was able to stay longer to enjoy all of the amenities. Highly recommend!
Guest favorite
A serene beach scene features two dogs running along the shoreline, their shadows stretching across the wet sand. The calm waves reflect sunlight, creating a shimmering effect on the water. A clear sky complements the tranquil setting.
Apartment in Sheboygan
4.89 out of 5 average rating, 97 reviews

The Beach | Sheboygan 2Br/1 Ba

CharlotteRating, 5 stars4 weeks ago
the place was great and we were so happy to be able to bring our dog with us. I was pleasantly surprised to see no dog hair from previous renters. very clean. Ashton and James were great! they were quick with all requests and super friendly. we had an emergency when we got back from our stay because my daughter left her koala lovey at the Airbnb. 😊 Ashton and James were prompt in their response and mailed the lovey to us. thank you!
Guest favorite
A calm pond reflects the surrounding trees and buildings under a clear blue sky. The landscape showcases a blend of greenery and structures, creating a serene atmosphere. The still water enhances the tranquility of the countryside setting.
Farm stay in Oostburg
4.94 out of 5 average rating, 100 reviews

Blue Barn on the Green and Farmhouse Retreat

RamintaRating, 5 stars1 month ago
The property was stunning, neat, and had a very homey feel to it. Everything was decorated beautifully with an old-style authentic look. Plenty of space and room offered to fit guests. Had a wonderful time with a beautiful view, highly recommend! Thank you!!!
Guest favorite
A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.
Home in Elkhart Lake
4.91 out of 5 average rating, 240 reviews

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

BarbaraRating, 5 stars1 week ago
Dan is a SUPER Host! His communication is 10/10! We were given the green light to check in early however, we couldn’t due to my husband’s work schedule. Dan has a very comfortable home to stay at. We stayed with 5 adults and 2 fur babies. We were able to purchase eggs from his sons ( delicious) took A dozen home. We had the best time at the home from the pin ball machines , watching movies to hanging out with our adult kids! Can’t wait to try one of Dan’s other properties.

Vacation rentals with pools in Sheboygan

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.
Apartment in Elkhart Lake
4.63 out of 5 average rating, 19 reviews

Siebkens Lockout Unit

JeffRating, 5 stars7 months ago
Perfect location - easy check-in.
Superhost
An indoor pool area features a clear water pool surrounded by a tiled border. A large screen is positioned for viewing, and sunlight streams through two windows, illuminating the space. Colorful pool toys and two lounge chairs add comfort and convenience.
Home in Newton
4.88 out of 5 average rating, 8 reviews

Country Cottage Indoor Pool HOT TUB NFL Draft ava

CassandraRating, 5 stars10 months ago
Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.
Guest favorite
The exterior of a two-story home is portrayed, featuring a welcoming front porch with potted plants. Lush green grass lines the pathway leading to the stairs. The facade combines traditional elements with modern updates, reflecting a craftsman style. A clear sky with scattered clouds adds to the scene.
Home in Plymouth
4.97 out of 5 average rating, 33 reviews

Private Home 4 BR+2Ba, Heated Pool by Road America

FrancoisRating, 5 stars4 months ago
Very nice house, ideal for us coming to town. We were 2 families with 4 kids and the place was the perfect size and convenient for all. The hot tub is a great addition, right next to the backdoor deck, very close actually from the house. Very clean and very flexible hosts, kitchen was great and the large dining table is perfect for 8 guests.
Guest favorite
An indoor pool area is surrounded by wood-paneled walls and expansive windows, allowing natural light to fill the space. Several blue chairs are positioned around the pool, and potted plants add a touch of greenery to the inviting setting.
Hotel room in Elkhart Lake
5 out of 5 average rating, 5 reviews

Resort Life 2 Queen Suite

CameronRating, 5 stars7 months ago
Great place in the heart of Elkhart Lake. Close to restaurants and an easy drive to Road America.
Guest favorite
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.
Apartment in Elkhart Lake
5 out of 5 average rating, 8 reviews

Resort Condo on Elkhart Lake

SamanthaRating, 5 stars9 months ago
Great stay on Elkhart Lake! Located in a central location, you can walk into town for dinner and also great lake amenities right on site. We rented a boat for the day and enjoyed the pool and beach access. We also greatly appreciate Pam being one of the few places we found that is dog friendly!
Superhost
An open studio layout features a spacious bed dressed in a white quilt with a decorative throw. A comfortable seating area with a loveseat is arranged beside the kitchen, which includes wooden cabinetry and dark bar stools. Warm lighting creates a welcoming atmosphere.
Villa in Elkhart Lake
5 out of 5 average rating, 4 reviews

First Floor Queen with Single Pull-out

SamRating, 5 stars9 months ago
A very nice experience overall. Very responsive with questions and the location is very convenient for swimming, ice cream, getting on the lake, etc.
An indoor pool is framed by natural stone and wood paneling, with large windows allowing natural light. Lounge chairs are arranged at one end of the pool, offering a relaxed setting. The pool area is spacious, creating a calming atmosphere for leisure activities.
Home in Plymouth

Road America lake house.

ChrisRating, 5 stars8 months ago
Jeff was a great host helping with all of our last minute needs. Extremely responsive and helpful! The house was just as described and the pool was a much needed touch after a long day. Can't recommend this place enough!!!
An open layout features a cozy sleeping area with a spacious bed framed by light walls and large windows. A modern kitchen with dark cabinetry and stainless steel appliances is complemented by a round coffee table on a textured area rug. A comfortable seating area is visible.
Condo in Elkhart Lake
New place to stay

Private Beach, Pools & Full-Kitchen

SaraRating, 5 stars1 week ago
Cute little airbnb in a private vacation rental community, but everyone is so close that it’s not very private. i wish i would’ve known beforehand that most businesses and some of the amenities such as the hot tub were still closed for the year… i think the price is steep for the off season since half the amenities weren’t available, but still had a nice retreat.

Quick stats about vacation rentals in Sheboygan

  • Total rentals

    270 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Sheboygan?

    Make yourself at home in Sheboygan by choosing from our most frequently booked neighborhoods. We have over 210 vacation rentals in James Madison, over 210 vacation rentals in King Park, over 270 vacation rentals in End Park, and over 210 vacation rentals in Business Drive North.

  • Are there vacation rentals with a dedicated workspace in Sheboygan?

    Yes! Work meets play with ease at over 140 vacation rentals in Sheboygan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Sheboygan?

    Experience the best of Sheboygan with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Sheboygan?

    Four-legged friends are welcome in Sheboygan. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Sheboygan have self check-in?

    Absolutely! We offer over 10 apartment rentals with self check-in in Sheboygan. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Sheboygan?

    Sheboygan has more than 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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