Apartment holiday rentals in Sheboygan County

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.

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

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

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.

Newly Updated! Downtown & Shore

Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally located, just 4 mins to downtown and 5 mins to the shoreline! Upon entry you are welcomed by a spacious living and dining area. Relax and unwind on new memory foam queen mattresses in all bedrooms! 43" Roku TVs in all bedrooms and 65" Roku TV in living area. Kitchen is fully stocked for meal preparation. Enjoy the coffee & tea bar! We are pet friendly!

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

Cactus Corner KING Apartment

This stylish, newly remodeled upper unit 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 facing the pretty garden below. The building has a shared laundry area in the basement with two new washers and dryers included for guest use. There is also ample off street parking and a lovely green space.

2BR Apt Near Beach & Downtown

Welcome to our charming 2-bed, 1-bath apartment just 2 blocks from the beach and less than a mile from downtown. With a fully equipped kitchen, comfy furnishings, and extra sleeping space for more guests, it's the perfect spot for your city getaway. Start your weekend with a delicious treat from Sunday Dough donut shop downstairs before exploring all that the area has to offer.

Rock skip from the lake!

Enjoy a stylish experience at this centrally-located place. This one bedroom apartment features furnished kitchen, tiled shower and sleeper sofa. Located in downtown it is surrounded by great dinning and nightlife. Walking distance to the boardwalk and the lake its a perfect little getaway. Close to Golf, Fishing and racing.