Apartment holiday rentals in Sheboygan County

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Top-rated apartment rentals in Sheboygan County

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Guest favourite

Rental unit in Sheboygan

4.97 out of 5 average rating, 141 reviews

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!

Superhost

Rental unit in Plymouth

4.63 out of 5 average rating, 290 reviews

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.

Guest favourite

Rental unit in Sheboygan

4.97 out of 5 average rating, 69 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!

Guest favourite

Rental unit in Sheboygan

4.86 out of 5 average rating, 7 reviews

Bird's View King Suite

This upper unit is close to everything, making it easy to plan your visit to Sheboygan. It is fully stocked with everything you need while away from home. Spacious and clean with a dedicated workspace and fast internet. Enjoy some fresh air on the balcony or grill out in the beautiful yard below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is ample off street parking and a lovely green space with picnic table and grill.

Guest favourite

Rental unit in Sheboygan

4.87 out of 5 average rating, 86 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!*

Guest favourite

Rental unit in Sheboygan

4.95 out of 5 average rating, 38 reviews

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

Guest favourite

Rental unit in Sheboygan

4.98 out of 5 average rating, 131 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.

Guest favourite

Rental unit in Sheboygan

4.92 out of 5 average rating, 458 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.

Superhost

Rental unit in Sheboygan

4.85 out of 5 average rating, 209 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

Guest favourite

Rental unit in Sheboygan

4.88 out of 5 average rating, 77 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.

Guest favourite

Rental unit in Waldo

4.98 out of 5 average rating, 270 reviews

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.

Superhost

Rental unit in Sheboygan

4.89 out of 5 average rating, 293 reviews

Spiritual Vibes Downtown Walk-up

New art and hand crafted decor. Some are even available for purchase, others are for guests to enjoy during their stay. Cozy, inviting, private apartment close to restaurants, shops and entertainment. Wonderful morning and evening light. Large deck for relaxing outdoors or enjoying the sun. We have a storage shed for bikes, strollers and the like if needed. Just give us the heads up and we'll give you the key.