Apartment vacation rentals in Sheboygan

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Popular amenities for Sheboygan apartment rentals

Weekly apartment rentals

Superhost
Apartment in Sheboygan

Charming 2bd/2bath condo

HeatherRating, 5 stars2 months ago
Cheryl was very responsive.
Superhost
Apartment in Elkhart Lake
4.73 out of 5 average rating, 41 reviews

Bed & Beer -4 bdrm above a bar

RyanRating, 5 stars2 weeks ago
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.
Apartment in Sheboygan
4.86 out of 5 average rating, 21 reviews

On Broadway

KevinRating, 5 stars1 week ago
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.
Superhost
Apartment in Sheboygan

Overlook Oasis - Walk to Lake | Ellis District.

BenRating, 5 stars1 week ago
Danielle’s place is a wonderful location with very nice amenities. Walking distance to downtown, the river front, and the beach.
Top guest favorite
Apartment in Port Washington
5 out of 5 average rating, 8 reviews

Mariner's Point Carriage House

TylerRating, 5 stars1 week ago
I couldn't say enough positive things about our stay at Lori's! beautiful location, beautiful space. Lori was flexible with out check-out and very responsive. I would recommend Lori's place for anyone looking to have a nice getaway in the quiant little turn or Port Washington.
Guest favorite
Apartment 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 favorite
Apartment in Kewaskum
4.96 out of 5 average rating, 48 reviews

The Cozy Country Farmhouse, Eisenbahn Suite

AprilRating, 5 stars2 months ago
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 !
Guest favorite
Apartment in Sheboygan
5 out of 5 average rating, 6 reviews

LoriRandyParkside come see us just off I43 garage

ClayRating, 5 stars1 day ago
Awesome stay! Lori was very responsive, the place was extremely clean, close to the downtown. Exactly what we were looking for.

Private apartment rentals

Guest favorite
Apartment in Campbellsport
4.97 out of 5 average rating, 34 reviews

'McJugger’s Loft:' Walk to Lake, Park, Restaurants

LoriRating, 5 stars10 months ago
Our second stay here -- Perfect place for our adult kids and us to gather for the weekend. Everything was great! We had everything we needed in such a beautiful, spacious living area. The food in the restaurant below (quesadillas are the best!); the Hamburger Haus next door and the little cafe just down the street make it easy to dine w/o cooking! We visited the winery not far away, which is a great venue for music and drinks in an outdoor setting. The best was Consuelo -- the perfect hostess! So glad we got to connect again to tell her how much we enjoy McJugger's Loft!
Guest favorite
Apartment 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.
Apartment 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!
Guest favorite
Apartment in Sheboygan Falls
4.86 out of 5 average rating, 7 reviews

Elegant Condo in Sheb Falls

AlbertoRating, 5 stars9 months ago
Great place to stay for Road America.... will definitely stay here again!
Apartment 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 favorite
Apartment 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!
Apartment 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!
Apartment in Port Washington
4.75 out of 5 average rating, 28 reviews

Lovely 1 bedroom rental. Newly renovated!

MargauxRating, 5 stars6 months ago
This is the second time we’ve stayed here. It was cute, very clean, and has a nice comfortable bed. Chrissy, the host, was responsive and kind. We will definitely stay here again!

Family-friendly apartment rentals

Top guest favorite
Apartment 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 favorite
Apartment 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 favorite
Apartment 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 favorite
Apartment 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.
Top guest favorite
Apartment in Port Washington
5 out of 5 average rating, 237 reviews

Beautiful Port home short walk to town and lake

AnitaRating, 5 stars2 weeks ago
Eileen was a phenomenal host! Great location, everything you need, walkable to all the wonderful things in Port. Great place - very welcoming! Visit!
Top guest favorite
Apartment in Port Washington
4.93 out of 5 average rating, 297 reviews

Homeport

MarvinRating, 5 stars1 week ago
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!

Quick stats about apartment rentals in Sheboygan

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$8,394 GYD before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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