Apartment holiday rentals in Sheboygan

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

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.

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

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,

Walk to Downtown & Farmer Market

Enjoy and Relaxing in this brand new upper apartment. Very spacious and private. Walk to downtown restaurants, bars, coffee shops, bakeries and farmers market. Large great room with large screen Tv and workspace. Kitchen has plenty of room and amenities to stay in if you choose. Whether its an early coffee at the Coffee bar or an afternoon glass of wine relax and enjoy Sheboygan. Stay 2 nights of 2 months. All supplied and ready for your short or long term stay.

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.