Holiday rentals in Sheboygan

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Sheboygan

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Oostburg

4.97 out of 5 average rating, 231 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

31 Oct – 7 Nov

€ 158 per night

Guest favourite

Townhouse in Sheboygan

4.97 out of 5 average rating, 117 reviews

Family Friendly Riverfront Escape|HUGE Game Room

Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.

24–31 Oct

€ 141 per night

Superhost

Flat in Sheboygan

4.84 out of 5 average rating, 63 reviews

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!*

21–28 Nov

€ 138 per night

Superhost

Flat in Sheboygan

5.0 out of 5 average rating, 3 reviews

Modern Lower Apt - One block to the Lake

Part 1 of 2 Amazing AirBnB apartments in this ideally located duplex. *Disclaimer - this apartment provides a true lower level living (LLL) *LOL* experience. You may notice some noise from your amazing upstairs Airbnb neighbors. But.. with all the great bars, restaurants, golf, fishing, and water parks 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.

2–9 Nov

€ 130 per night

Guest favourite

Guest suite in Sheboygan

4.92 out of 5 average rating, 66 reviews

Cozy 1BD RM W/ fireplace by lake

Located three blocks east of downtown in a quiet classic neighborhood called the Ellis Historical District, this completely renovated 18th century 1 BD RM upper unit with a queen size bed, wall mounted fireplace welcomes your arrival. Easy access to the unit using a keyless code. The kitchen has a variety of pots , pans and spices for your cooking needs. Keurig coffee maker with k-cups, creamers and sugar. The bathroom has rain shower head. Shampoo, conditioner, body wash provided.

30 Mar – 6 Apr

€ 105 per night

Guest favourite

Flat in Sheboygan

4.98 out of 5 average rating, 89 reviews

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.

6–13 Dec

€ 143 per night

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 151 reviews

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.

19–26 Jun

€ 170 per night

Guest favourite

Flat in Sheboygan

4.92 out of 5 average rating, 394 reviews

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.

2–9 Jan

€ 89 per night

Guest favourite

Apartment in Sheboygan

4.87 out of 5 average rating, 192 reviews

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

7–14 Mar

€ 170 per night

Guest favourite

Home in Sheboygan

4.91 out of 5 average rating, 69 reviews

Spacious MCM Vibe Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our mid-century-modern 3 bedroom home near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

7–14 Nov

€ 145 per night

Guest favourite

Flat in Sheboygan

4.84 out of 5 average rating, 183 reviews

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

10–17 Feb

€ 66 per night

Guest favourite

Flat in Sheboygan

4.88 out of 5 average rating, 48 reviews

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.

9–16 Jun

€ 105 per night