Apartment holiday rentals in Sheboygan County

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Popular amenities for Sheboygan County apartment rentals

Weekly apartment rentals

Apartment in Elkhart Lake

4.63 out of 5 average rating, 19 reviews

Siebkens Lockout Unit

JeffRating, 5 stars3 months ago
Perfect location - easy check-in.

Private room in Sheboygan

4.96 out of 5 average rating, 23 reviews

Stunning Riverfront/ Lake Michigan S Pier Location

JoAnneRating, 5 stars8 months ago
I enjoyed my stay with Crissy. Clean place, and easy to find. I felt right at home.
Guest favourite

Apartment in Sheboygan

5 out of 5 average rating, 62 reviews

Recombobulation Station-Locally Owned Escape

ScottRating, 5 stars1 month ago
Missy's place is a very well-done rehabilitation of the upper story of an older residential Sheboygan home. It feels spacious, and the rehab work was done professionally with high-quality materials. Seating in the living room is comfortable - we watched the Packers dominate the Seahawks, and the window treatments are simple to operate and afford privacy from the neighbors. The kitchen is well-equipped, we liked the dining counter and the house was comfortable during the onset of winter with even heating and no drafts. The bed was comfortable and the water pressure in the shower was fantastic. The location is great. We could walk to the lake in minutes, and eateries ranging from gastropubs to dive bars were just a few blocks away. Kohler's contemporary arts museum is just down the street. Yet the neighborhood is quiet and uncongested. Our three-day getaway was everything my wife and I could have hoped for.
Superhost

Apartment in Sheboygan

4.9 out of 5 average rating, 127 reviews

Sheboygan Surf House - North Point

AngieRating, 5 stars2 months ago
I've been here several times before, and it's the easiest part of sheboygan to be in if you don't have a car, you're vegan, like to go to the lake, etc! Lots of food options, and very walkable

Apartment in Sheboygan

4.96 out of 5 average rating, 26 reviews

Helene's room

MattRating, 5 stars22 months ago
Really excellent, high quality breakfast on top of everything else being stellar as well!

Private apartment rentals

Guest favourite

Apartment in Sheboygan

4.82 out of 5 average rating, 83 reviews

The Garden | Sheboygan 2 Br/1Ba, Pet Friendly

JeannieRating, 5 stars1 month ago
Adorable decor. Convenient location. Responsive hosts. Quick snow removal. My stay was perfect.
Superhost

Apartment in Sheboygan

4.9 out of 5 average rating, 10 reviews

Logan Ave Holiday House - Upper

JeffRating, 5 stars5 months ago
Chris took care of me place was clean, cozy, everything you needed was supplied. perfect location with plenty of places to eat, I will definitely reach out again if I'm ever in Sheboygan. 10/10.
Superhost

Apartment in Elkhart Lake

4.74 out of 5 average rating, 38 reviews

Bed & Beer -4 bdrm above a bar

RyanRating, 5 stars5 months ago
Beautiful place. Great amenities
Guest favourite

Apartment in Sheboygan

4.88 out of 5 average rating, 8 reviews

Parkside Studio Apartment

ParkerRating, 5 stars1 month ago
Ashlynn’s place was a more last minute decision, and we couldn’t have been happier with our choice. Communication was beyond great, and they were very accommodating. The place was very nice and clean. Would recommend to anyone!
Guest favourite

Apartment in Sheboygan

4.88 out of 5 average rating, 78 reviews

One Bdrm Apt - The Erie House near lake & downtown

DeborahRating, 5 stars3 months ago
Wonderful location, everything you need is available. Lovely neighborhood.
Guest favourite

Apartment in Sheboygan

4.97 out of 5 average rating, 72 reviews

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

EthanRating, 5 stars1 month ago
Stayed here with my wife, sister and brother-in-law while visiting family for the holidays. This place was amazing and a great deal! The apartment itself is very spacious and comfortable. It was also very nicely decorated for the holidays! The location is very walkable to eight street and the lake. Would highly recommend!
Guest favourite

Apartment in Sheboygan

5 out of 5 average rating, 38 reviews

The Sheboygan Foodie Flat

JustinRating, 5 stars4 weeks ago
This stay was exactly as promised. Very quiet neighborhood and unit. Completely stocked with everything you could need, clearly the hosts have spent quite a lot of time thinking this through. Very high quality linens, towels, bed mattress, etc. When I arrived there was easily $50 worth of starter groceries and snacks provided which were a really thoughtful touch. Will stay again.

Family-friendly apartment rentals

Guest favourite

Apartment in Waldo

4.98 out of 5 average rating, 272 reviews

The Blue Cobb House

RebeccaRating, 5 stars1 month ago
Jewel is a wonderful host! Her place is a quiet and relaxing place to stay while visiting family and friends in the area. Whenever I visit the area, I check to see if Jewel’s place is available first before looking anywhere else!
Guest favourite

Apartment in Kohler

4.99 out of 5 average rating, 137 reviews

Washington Walk Historic House w/elegant spa bath

CynthiaRating, 5 stars1 month ago
Washington Walk is our favorite Airbnb anywhere. A luxurious respite all in itself, with great hiking, dining, shops, and a cool art museum nearby. We opted to stay an extra day. Kristine has thought of everything (including wine and chocolates) and went out of her way to arrange flexible checking and out times. We ended up opting to extend our stay.
Guest favourite

Apartment in Elkhart Lake

4.99 out of 5 average rating, 69 reviews

Downtown Elkhart Lake - The Quintessential Suite

AmyRating, 5 stars3 months ago
We have stayed with Ryan several times because of the great location, excellent communication, and the clean and comfortable accomodations. The space is exactly as pictured and has all the amenities you will need for a great vacation. Highly recommend!
Guest favourite

Apartment in Elkhart Lake

5 out of 5 average rating, 59 reviews

Lime Ridge Guest House

MikeRating, 5 stars6 months ago
We stayed with our eldest son and youngest grandson to attend the vintage race weekend at RA. VERY close to restaurants in Elkhart Lake and also the track. Beds were fantastic and the home is spacious. Our grandson enjoyed the swingset playground too. We ended up cooking two meals using the gas grill and deck and the kitchen was well equipped. Our grandson didn’t want to leave. Four “real” bedrooms and we will be back with more people next year. We had few questions but they were answered immediately. If you are planning to attend an RA event I highly recommend staying here. If you plan to attend the Brian Redmond vintage event next year you will be competing with us hahaha.

Destinations to explore