Apartment holiday rentals in Sheboygan

We loved this quaint apartment & would definitely stay again! It was extremely clean and cozy. Cody was a top tier host! He made check in a breeze and responded quickly each time!

This place is a hidden gem for air bnbs. They had so much to offer and went above and beyond to even suggest places to eat! The place was so clean and was an amazing experience.

Eric’s place was wonderful! The location was fantastic. Walking distance to downtown, and close to the water. Though we were arriving late, Eric reached out to let us know we could come in early. His communication was excellent prior, during, and after our stay. I would definitely stay here again!

Julie’s place was quiet and peaceful for a quick getaway to Port Washington! She was very friendly and kind to my dog, and made me feel right at home as a solo traveler. Would recommend to anyone visiting the area who prefers to be away from the hustle and bustle of a big city.

I absolutely loved Samantha's place. The living room had great views and was so cozy to curl up with a book. The balcony was perfect for a cup of tea in the morning and watching the neighborhood wake up. There are plenty of restaurants to walk to add well as cute shops to check out. I would love to return again sometime!

Great place with plenty of room for our family while in town!! Was so thankful to have found this place!! Location was perfect and close to all our family events while in town!!! Loved staying here!!!

Very clean and as the pictures presented! Walkable to Lake MI! Cozy, but comfortable for myself and spouse, two teenage boys and my senior mother! Kitchen had everything we needed to make breakfast each morning!

Lynk and Emma’s place is fantastic! 4 C’s— Clean (sparkling) Convenient (nestled in Downtown with its own parking spot)) Comfy (exactly as photos show) Cute (so many nice touches!) And Q is for quiet, great for sleeping well. We really enjoyed our stay and all that Port Washington offers. We highly recommend their place!

Cheryl was very responsive.

Thank you for the hospitality. Always nice to be close to the Brown Baer for a Crunchwrap and a drinkie. Looking forward to next time.

The property was exactly as described and perfect for our stay. Elizabeth’s place was impeccably clean and tidy. Communication was very responsive and she went out of her way to accommodate us. If you’re looking for just the right place to stay in Sheboygan then this is the place.

Danielle’s place is a wonderful location with very nice amenities. Walking distance to downtown, the river front, and the beach.

Great place to stay for Road America.... will definitely stay here again!

Was traveling solo and found the Carriage house to be easy to find and get into thanks to Lori's instructions. The finishes (countertops, window blinds, shower) are so lovely. It's nice to be able to enjoy a place that doesn't look like every other boring AirBnB. The bed was comfortable and the neighborhood was so quiet and walkable. The book of instructions and recommendations was a great resource. I had a few hours to relax in between activities and had a fun, cozy time watching a movie, listening to the gentle rain outside and enjoying some homemade treats provided by the hosts. When the sun came out, the neighbors could be seen walking their dogs, gathering together at local spots, and enjoying the lake. I can't wait to come back in the Fall.

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!

Connie and rich were amazing host . They showed love and kindness to us . If I need a place in kewaskum again i definitely would rent the place out again . Very beautiful place !

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!!!

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!!

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!

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.

Eileen was a phenomenal host! Great location, everything you need, walkable to all the wonderful things in Port. Great place - very welcoming! Visit!

Amy was a great host! She was very responsive to all of our questions and made us feel very welcomed. We loved being right by the lake and within walking distance to the shops and restaurants. An unexpected surprise was waking up Saturday morning to find an art festival right outside our door! My wife was like a kid in a candy shop, we love street festivals. We would absolutely stay again!