Holiday rentals in Sheboygan

Storybook Home - 1 mi to Lake & Downtown Sheboygan

Welcome to The Fox & Folly Inn 🦊 —a unique whimsical retreat. Perfect for families and those who are kids at heart! 🖼️ Creative and cozy home with art and murals. 🦊🐰🦉Themed with original characters. Audio stories & endless charm! 🛏️ Master Bedroom - King Bed 🛋️ 2nd Bedroom - Bunk Bed = Full Lower, Twin Upper 🛌 Sleeps 5 🛁 1 Full Bathroom - Towels, Hair Dryer+ 🍽️ Fully Stocked Kitchen 🅿️ Off-Street Parking 🏖️Minutes from the beach & Bookworm Gardens 📖Your storybook adventure awaits!

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!

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Spacious/stylish, 2br loft

Beautiful, spacious loft in active downtown. Laundry, kitchen, 1.5 baths, 2 Qu, 2 Tw beds. Bakery & fitness studio on 1st floor (some a.m. noise). Stocked w/home essentials. Smart TVs, free WIFI. Pay-as-you-go parking in rear but free nights/weekends. 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.

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

The Suncatcher -Steps from Lake - Fenced Yard

Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.

*Front porch, fenced in backyard- PetsWelcome*

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!