Apartment holiday rentals in Sheboygan

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

Sheboygan Surf House - North Point

This super spacious studio apartment is the largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for beach days, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment offers a true lower level living experience. You may notice some noise, including foot traffic, from your amazing upstairs Airbnb neighbors. But.. with all the great restaurants, golf, fishing, and the beach nearby you won’t even have the time to hear it! Located only 1 block from the beach on Lake Michigan - you’ll find relaxation and a great time here at the heart of Sheboygan’s Shoreline.

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 2BR Upper Apt • Quiet Area • 1 Mile to Beach

Looking for a clean, comfortable, and budget-friendly place in Sheboygan? You’ve found it. This 2-bedroom, 1-bath upper-level apartment is perfect for travelers who want a quiet place to relax — just 1 mile from the beach and close to everything, without the noise (or the price tag) 📶 Fast, free Wi-Fi – Work, stream, or scroll with ease 🅿️ Plenty of street parking – Always free ✅ No pets, no parties — just peace and quiet ✅ Perfect for couples, solo travelers, small families,

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.

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.

Washington Walk Historic House w/elegant spa bath

This 1880's Historic Riverside Tavern was completely remodeled in 2017, maintaining as much of the original character as possible. The Village of Kohler moved the building to its' current location in 1908 - eventually closing the tavern to establish the Kohler Women's Club in the 1920s. It opened with a tea room on the first floor as well as the upstairs being home to the original Kohler Girl Scouts.