Apartment holiday rentals in Sheboygan County

Find and book unique apartments on Airbnb

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Popular amenities for Sheboygan County apartment rentals

Weekly apartment rentals

Guest favourite
Flat in Elkhart Lake
4.88 out of 5 average rating, 16 reviews

Elkhart Lake Flat - 3 Min to Road America

JasonRating, 5 stars9 months ago
Great value! Perfect location for a racetrack visit. No frills but coffee maker and toaster and comfy beds. Great for the price. Not walking distance to anything really but easily accessible. Will stay there again happily! Thank you!
Guest favourite
Flat in Sheboygan
4.95 out of 5 average rating, 20 reviews

Home away from home

Kirsten Rating, 5 stars10 months ago
What a gem! I truly think this property is highly undervalued. The grounds alone are magnificent. Such a gorgeous historic home and peaceful neighborhood. It felt private and secluded yet close to everything that we needed to get to and very walkable safe area. I cannot say enough good things about this Airbnb and hope to stay there again on future trips! Thank you to our wonderful Host, Julie, who was responsive, kind, and very accommodating of us.
Flat in Sheboygan
4.84 out of 5 average rating, 31 reviews

Helene's room

EmilyRating, 5 stars1 week ago
We absolutely loved our stay! Our first time at a bed and breakfast! Can’t say enough about how great Ashley was! She greeted us upon our arrival and gave us a tour of the property. We got up early for a fishing trip and she had set us aside a breakfast to go and the second day brought us breakfast to our room! She gave great fish fry recommendations as well! We loved having the lake view from our room!
Flat in Sheboygan
4.8 out of 5 average rating, 5 reviews

Sheboygan Getaway w/ Deck + On-Site Lake Access!

ZenaidaRating, 5 stars10 months ago
Amazing place to relax , Mary was very nice and friendly, she made us feel at home , the loft is beautiful and we enjoyed the place so much that 2 nights were not enough, we could have stayed more nights as Sheboygan has so many things to offer , I really enjoyed the sunrise and watching the pristine Lake Michigan on the deck , breathtaking views !!!
Guest favourite
Flat in Elkhart Lake
5 out of 5 average rating, 8 reviews

Resort Condo on Elkhart Lake

SamanthaRating, 5 stars9 months ago
Great stay on Elkhart Lake! Located in a central location, you can walk into town for dinner and also great lake amenities right on site. We rented a boat for the day and enjoyed the pool and beach access. We also greatly appreciate Pam being one of the few places we found that is dog friendly!
Flat in Sheboygan Falls
4.92 out of 5 average rating, 12 reviews

Country Apartment

StaceyRating, 5 stars22 months ago
Great place! Peaceful, country setting with places to eat within a short drive! It was super quiet! Would stay again!
Guest favourite
Flat in Sheboygan
4.95 out of 5 average rating, 57 reviews

North 7th Place - Spacious 2 Bedroom Lower Unit!

Shelley MRating, 5 stars2 months ago
We stayed at Chris’s place to visit nearby family with our two children and dog. The apartment was perfect for us: comfy beds and sofas; well-stocked kitchen; loads of games and books for entertainment. Lake Michigan is blocks away, and we took several (longish) walks to the beach and downtown shopping. Chris was quick to return texts, and he was a great host. 10/10 would return!
Guest favourite
Flat in Plymouth
5 out of 5 average rating, 31 reviews

Private Retreat near Road America and Elkhart Lake

FrankRating, 5 stars9 months ago
Had a long weekend at Road America so wanted to stay close so I could get back and forth during the day. This place was a perfect fit. Like 7-8 minutes to the track and the perfect amount of space. Nice and quiet so I could sleep with the countryside right outside the door. Btw, love that bench by the door. Perfect spot to sit and take my shoes off and park my backpack. You’re 5-10 minutes from downtown Plymouth and Elkhart Lake. Dozens of restaurants, stores and whatever else you need. Great place!

Private apartment rentals

Flat in Elkhart Lake
4.63 out of 5 average rating, 19 reviews

Siebkens Lockout Unit

JeffRating, 5 stars7 months ago
Perfect location - easy check-in.
Flat in Elkhart Lake
4.92 out of 5 average rating, 24 reviews

Cozy Unit w/ Patio: Walk to Dining, Lake Elkhart!

TanyaRating, 5 stars12 months ago
We loved the neighborhood and were within walking distance to all the things. We were able to travel with our dog, and really appreciate a dog friendly rental.
Flat in Sheboygan

North side Sheboygan, great area

DerekRating, 5 stars45 months ago
Patrick was a phenomenal host who went above and beyond to make our Ryder Cup experience unforgettable!!! The residence was clean, stocked, and in a VERY nice neighborhood!!!! I highly recommend Patrick to anyone who is going to the Sheboygan area!!!
Flat in Sheboygan
4.14 out of 5 average rating, 7 reviews

Cozy and Modern Upper Near Lake

AmyRating, 5 stars1 month ago
Perfect place for a quick trip to Sheboygan. Would for sure stay here again if we were back in the area! All the details were clearly communicated and even gave some great advice on places in the area to dine out.
Top guest favourite
Flat in Kohler
5 out of 5 average rating, 183 reviews

Church Street Romance & Retreats-Village of Kohler

DebiRating, 5 stars6 days ago
We had an absolutely wonderful experience at this Airbnb! From the moment we arrived, we felt right at home—the space was beautifully cozy, impeccably clean, and thoughtfully designed for comfort. The location was ideal, making it easy to explore the area and enjoy everything it had to offer. Every detail was well considered, from the comfortable furnishings to the little touches that made our stay effortless. Whether relaxing after a day out and about or enjoying a quiet morning, this place was perfect for our needs. On top of that, Kristine was incredibly welcoming, responsive, and ensured everything was seamless. We couldn’t have asked for a better stay and would gladly return. Highly recommend to anyone looking for a delightful home away from home!
Flat in Sheboygan
4.44 out of 5 average rating, 9 reviews

Welcome to Harbor Nights!

ScottRating, 5 stars1 week ago
Andrew’s place was great! It’s in a great location overlooking Lake Michigan and there is a lot to do within walking distance. Everything was clean, in great shape with everything needed. Getting in was a breeze and Andrew had great communication. Thanks!
Flat in Elkhart Lake
4.43 out of 5 average rating, 7 reviews

Welcome to the farm house!

JohnRating, 5 stars22 months ago
We had a great weekend at Road America and Clinton’s place was conveniently located just minutes away. It was as described, simple and very clean. The property was well kept and a beautiful setting with plenty of space to park. We basically slept and showered there and it met all our needs. In addition, Clinton was an extremely nice and responsive host. We’d definitely stay there again if visiting Road America. :-)
Flat in Plymouth
4.82 out of 5 average rating, 11 reviews

Kettle Edge Retreat and Gardens

KatelynRating, 5 stars34 months ago
Fantastic stay on beautiful property. Very clean with EXCELLENT communication. Our first time in the area, we really appreciated all the help and the dining suggestions. Highly recommended.

Family-friendly apartment rentals

Top guest favourite
Flat in Waldo
4.98 out of 5 average rating, 279 reviews

The Blue Cobb House

MikeRating, 5 stars1 month ago
My wife and I were celebrating our 45th Wedding Anniversary- Jewel made it so special for us! And her place? WOW! We’ve stayed in AirBnb’s from Olympia to Siesta Key, from Zagreb to Dubrovnik- and Jewel’s place and her hospitality outshines them all! Beautiful accommodations, spotless, every possible provision, comfortable and supportive bed, - it was simply heavenly!!! Thanks to Jewel!!!
Top guest favourite
Flat in Kohler
4.99 out of 5 average rating, 140 reviews

Washington Walk Historic House w/elegant spa bath

JohnRating, 5 stars3 months ago
Kristine was an amazing hope with such thoughtful touches. She personalized our stay perfectly after a brief conversation. She had perfect recommendations and was such a kind, considerate person. And that’s not even to mention how amazing the space was!! Such amazing mattresses, perfect decor and the best decor in any airbnb ever. Classic, classy Midwestern living through and through!!
Top guest favourite
Flat in Elkhart Lake
4.99 out of 5 average rating, 71 reviews

Downtown Elkhart Lake - The Quintessential Suite

TanyaRating, 5 stars1 week ago
We absolutely love this place! Will definitely come back. The place is very comfortable; we felt right at home and had everything we needed for our stay. The hosts are very friendly and accommodating. Thank you Ryan!
Guest favourite
Flat in Elkhart Lake
5 out of 5 average rating, 59 reviews

Lime Ridge Guest House

MikeRating, 5 stars11 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