Apartment holiday rentals in Sheboygan County

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!

Parkside Studio Apartment

Escape to this peaceful family retreat next to a wooded park! Just 2 mins. from Lake Michigan, 5 mins. from Kohler-Andrae State Park, and 10 mins. from the harbor, our spacious, newly remodeled studio offers the perfect getaway. It's ideal for families with a king bed, bunk bed, and pullout queen sofa. Enjoy free Wi-Fi, Smart TV, a dedicated workspace, and hassle-free parking. Whether exploring the outdoors or simply unwinding, this cozy haven has all the comforts you need for a memorable stay!

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

Charming Historic Lower Unit King/Queen Sleeps 6

Beautifully restored lower unit with high, detailed ceilings and stylish historic charm. Sleeps 6 w/King and Queen-sized bedrooms, and a large sleeper sofa. Spacious and open with a fully stocked kitchen and gorgeous dining area! Off-street parking, centrally located 1 mile from the beach, Asian hot-deli across the street! Just a 10-min walk to close-by bars and food spots, or 3 min drive to downtown restaurants, boutique shops, parks. Perfect for relaxing getaways or work-friendly stays!

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

Overlook Oasis | Coastal Haven in Ellis District

Welcome to Overlook Oasis by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Nestled in Sheboygan’s historic Ellis District, this newly remodeled upper-level retreat blends modern comfort with coastal charm. With 2 queen beds and a versatile king trundle, it’s perfect for families, couples, or groups. Step outside to the scenic lake walk, grab ice cream at Blast, or sip cocktails at Harbor Lights Bar—all just minutes away.

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.

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.

One Bdrm Apt - The Erie House near lake & downtown

This house was built in 1888 as a single family home and retains its nineteenth century charm along with today's modern conveniences. The location is just walking distance from both majestic Lake Michigan to the east and Sheboygan's charming downtown to the west. The lodging, which sits in an attractive, tree lined neighborhood, has been divided into several living units in which you will be staying on the first floor facing Erie Avenue.

Charming 2bd/2bath condo

This charming and very peaceful 2 bd, 2 bath condo is nicely located close to everything. 6-7 blocks from the lake and a short drive to either downtown or the highway. It is just a block off one of the cities main roads, so ease of access is amazing. Its perfect for short stays and longer stays alike with all of its amenities. This is an upper unit so there are stairs to enter the condo. There is a parking lot for guests to use.

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

NEW Riverfront Loft - Fantastic location

This riverfront loft truly offers the best combination of views and location in Sheboygan. Situated right on the boardwalk over the river where the river meets the lake. Boutique shops, highly rated restaurants, spas, and Charter fishing are all right there to enjoy. Peaceful & private: located above a business so after hours you will have peace & privacy with no other residential properties on this side of the river.