After coming back from my trips abroad, I have fallen in love with Airbnb. I wanted to find ones that felt really Sheboygan-y. You know, beachside, vintage, and/or cozy cottages… Turns out, there are some amazing options here! Below are just a few of the Sheboygan Airbnbs I found. Some are for one or two people while others can house up to eight. Click on the photos to get booking details.

 (*psst* these photos are not mine. They are directly from Airbnbs website.)

Little Wisconsin Getaway

Rate | $65/night

Sleeps | 4

Description | Cozy and comfortable 2nd story condo. Lovingly decorated and looking for guests to enjoy. The setting is next to the Pigeon River and is bordered by oak and maple trees. Enjoy a cup of coffee or glass of wine on the balcony.

Sheboygan Surf House “Jetties”

Rate | $68/night

Sleeps | 2

Description | This newly remodeled 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 and South Pier.

Sheboygan Surf House “The Elbow”

Rate | $75/night

Sleeps | 2

Description | This newly remodeled 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 and South Pier.

Vintage Sheboygan

Rate | $99/night

Sleeps | 7

Description | This charming home has abundant natural light and modern furnishings with vintage architectural details.

The Humboldt House

Rate | $115/night

Sleeps | 5

Description | Welcome to the gorgeous bluffs of Sheboygan’s Lake Michigan waterfront! The lakefront home is perfect for a romantic getaway, girls weekend, golf trip, or fun family vacation year round. Close to town, shops, bars & restaurants!

Beachside Getaway

Rate | $150/night

Sleeps | 4

Description | Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning views. You can listen to the waves or walk just a few feet and have the sand on your feet.

Beachfront getaway in Sheboygan

Rate | $150/night

Sleeps | 8

Description | One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun.

Beach and golf house

Rate | $200/night

Sleeps | 8

Description | This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic Ellis district on the shores of beautiful Lake Michigan. The home is a 2 or 3 minute walk to Deland Beach and the Sheboygan Marina and lighthouse. A short drive to world class golfing at Whistling Straights, Black Wolf Run and The Bull.

Bright and Beautiful Lake Escape

Rate | $200/night

Sleeps | 8

Description | Welcome to the gorgeous bluffs of Sheboygan’s Lake Michigan waterfront! Their lakefront home is perfect for a romantic getaway, girls weekend, golf trip, or fun family vacation year round. Close to town, shops, bars & restaurants!

Updated Sheboygan Home

Rate | $233/night

Sleeps | 7

Description | Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bath Sheboygan vacation rental! When you’re not relaxing at home, take the 10-minute walk down to the lakefront beach.

The Logan House 

Rate | $250/night

Sleeps | 6

Description | Recently renovated & charming 3/1.5 on the north side of Sheboygan. Great location – Close to Lake Michigan and downtown, dining and activities. Six miles to Whistling Straits.

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