Apartment holiday rentals in Sheboygan County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Sheboygan County

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Flat in Sheboygan

4.96 out of 5 average rating, 28 reviews

North 7th Place - Entire Unit- 2 bedrooms

A quiet cozy 2 BR space just a few minutes walk to the beautiful Lake Michigan. Conveniently located less than a mile from downtown Sheboygan, where you can enjoy locally owned shops, charming restaurants, and a fun night out! Other amenities include; free use of the back yard, fire pit, outdoor grill, Wi-Fi, Netflix, work space, sunroom, spin bike, fully equipped kitchen, onsite laundry, and you can bring your pets! Please check us out, as our family would love the opportunity to host you!

7–14 Jul

$195 SGD per night

Guest favourite

Flat in Sheboygan

5.0 out of 5 average rating, 38 reviews

Quaint Blast from the Past - walk to lake/8th st

Renovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our "Blast from the Past" as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!

14–21 Dec

$156 SGD per night

Guest favourite

Flat in Sheboygan

4.96 out of 5 average rating, 26 reviews

A Wave From It All! - Lake Condo

Welcome to Lake Michigan! Fish, surf, shop or golf, this condo is close to it all. Easy secure entry, ground floor. The boardwalk (South), offers green space, tables, restaurants, scenic water views and walking areas. Head North to almost a mile of beach, playgrounds, tennis courts, lake history and the recovered remains of Great Lakes schooner Lottie Cooper capsized in 1894. We provide accommodations for four, this 2-bedroom 1-bathroom condo has a full kitchen, living room and street parking.

26 Sep – 3 Oct

$198 SGD 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!*

15–22 Oct

$126 SGD per night

Guest favourite

Flat in Sheboygan

4.95 out of 5 average rating, 20 reviews

Peaceful apartment by 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

22–29 Oct

$164 SGD 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.

7–14 Jan

$157 SGD 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.

31 Dec – 7 Jan

$176 SGD per night

Guest favourite

Flat in Sheboygan

5.0 out of 5 average rating, 22 reviews

The Sheboygan Foodie Flat

Schnazzy upper flat in the heart of Sheboygan’s Eastside. Walk to Lake Michigan Beaches, Riverfront, Uptown and Downtown. Enjoy the newly renovated 2nd floor of an 1893 historic rambler with lots of natural light. -Desirable Eastside, with walkable neighborhoods. -Large Italian tile walk-in shower with Kohler fixtures. -Fully equipped kitchenette with microwave, convection oven, two-burner hot plate, Keurig, coffee pot & toaster. -New furnishings -Sheboygan Foodie Guidebook

12–19 Sep

$165 SGD per night

Guest favourite

Flat in Sheboygan

4.92 out of 5 average rating, 398 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.

16–23 Feb

$112 SGD per night

Guest favourite

Flat in Kohler

5.0 out of 5 average rating, 158 reviews

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

1–8 Jul

$313 SGD per night

Guest favourite

Flat in Sheboygan

4.84 out of 5 average rating, 184 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

5–12 Mar

$85 SGD 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.

8–15 Mar

$126 SGD per night