Top Cottages in Sheboygan in 2026

Aerial view of Deland Park (North Beach) and residential area in Sheboygan WI

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Our top choices for Sheboygan cottages

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Two Rivers

฿13,325 total

includes taxes & fees

14 Jun - 15 Jun

Large Backyard, Walk to Hospital: Sheboygan Abode!

Sheboygan

฿13,378 total

includes taxes & fees

7 Jun - 8 Jun

Walk to Beaches + Restaurants: Elkhart Lake Escape

Elkhart Lake

Walkable Thiensville Retreat Near Hiking!

Thiensville

฿16,723 total

includes taxes & fees

21 Jun - 22 Jun

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Top Sheboygan Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent

"Great hotel! Newer, nice and clean. Friendly staff, great bar. Loved everything."

Watershed Hotel

10/10 Excellent

"One of the best and cleanest hotels i have ever stayed at. If/when I return to Wisconsin, I will 10000% be booking at this hotel again. The staff and people at the front desk couldn't have been nicer. A 10 out of 10 stay for me. I stayed on the river side and being able to open up the door every morning to the Sheboygan River was the cherry on top. Fantastic hotel"

Grandstay Residential Suites Hotel - Sheboygan

6/10 Okay

"Room was spacious and clean. Central location close to restaurants and the beach. All walkable and felt safe walking around. Property was very dated, workout room was tight and cramped with 3 cardio machines in there. Small indoor pool, good for kids. When I arrived around 8-9pm, there was no one at the front desk. I had to wait around for 10 minutes or so before someone finally showed up. There were a few times that I went down to the lobby when I needed to buy a water or came in after dinner late and no one was at the front desk. Not sure if that is normal or maybe they were short staffed in the 2 days I was there? Feels odd not to have a friendly staff member at the front especially late at night when anyone can walk through the doors since the doors remain unlocked. They also don’t have daily housekeeping. I was only there for 2 nights so it was no big deal. On the last day housekeeping was knocking on my door 20 mins before checkout despite the do not disturb. I said I’d be out by checkout and she pre-thanked me if I decided to leave a tip. I thought that was odd. Tip for what I’m not sure since they don’t offer daily housekeeping and didn’t request anything. Price was also high compared to a modern hotel I paid for the night before in Madison. Maybe limited options in sheboygen?"

La Quinta Inn by Wyndham Sheboygan

6/10 Okay

"The staff was very friendly. Our room had some grimey stuff on the cabinet of the fridge that was very sticky. There were crumbs and stuff in the corners by the bed. A lot of light was coming through the door frame. And there were holes in the blackout curtain. Room smelled slightly of smoke. Bed was one the most comfortable beds I have slept on. Not bad, but needs some improvements."

AmericInn by Wyndham Sheboygan

6/10 Okay

"We stayed 2 nights for the Road America Motorcycle racing event. We stayed here last year as well. There was a boys soccer tournament that weekend also and there was a group that stayed at the hotel as well and very frustrating that they were not respectful to other guest and the hotel staff did nothing about them or the parents. They were running in the halls, screaming, knocking on all the doors. The breakfast area was hard to use and food was gone by 7:30 am. The hotel did have new carpet. So it was clean in that respect."

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent

"I didn’t catch the woman’s name, but the lady working all weekend was incredibly helpful. She gave us great recommendations for things to see and do while visiting Sheboygan, and she was so kind and welcoming. The breakfast was really good, and the hotel was in a perfect location. We would definitely stay here again if we’re ever back in town!"

Find out more about Sheboygan

Sheboygan Cottages information

Number of reviews
Accommodation	48 Cottages
Lowest Price	฿13,325
Highest Price	฿16,723

Frequently asked questions

How much do cottages in Sheboygan cost?

Prices for cottages in Sheboygan range between ฿13,325 and ฿16,723 per night. No matter your budget, you'll find the ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Sheboygan with Expedia?

We think that vacays should be a breeze, so if you're after cottages in Sheboygan at a great price, Expedia has got you covered. Save those pennies and select a cheap option surrounded by nature, or book an upmarket cottage to pamper your loved ones.

How can I find cheap cottages in Sheboygan?

The easiest way to locate cheap cottages in Sheboygan is with Expedia's useful filter tool. Refine your search results by star rating, amenities and budget to snag awesome rates in just a few keystrokes.

What is there to do in Sheboygan near my cottage?

You'll find loads of terrific things to see and do in Sheboygan. Don't miss major attractions like Sheboygan County Historical Museum, Blue Harbour Resort & Conference Centre Water Park and Whistling Straits Golf Course. John Michael Kohler Arts Centre, Stefanie H. Weill Centre for the Performing Arts and Above & Beyond Children's Museum are also visitor favourites.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sheboygan cottages

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Walk to Beaches + Restaurants: Elkhart Lake Escape

Walkable Thiensville Retreat Near Hiking!

Find holiday rentals that suit your style

Top Sheboygan Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

Watershed Hotel

Wingate by Wyndham Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

La Quinta Inn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

Quality Inn Sheboygan North I-43

Super 8 by Wyndham Sheboygan WI

Holiday Inn Express Sheboygan-Kohler by IHG

Find out more about Sheboygan

Sheboygan Cottages information

Frequently asked questions

Search Cottages in Sheboygan

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sheboygan cottages

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Walk to Beaches + Restaurants: Elkhart Lake Escape

Walkable Thiensville Retreat Near Hiking!

Find holiday rentals that suit your style

Top Sheboygan Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

Find out more about Sheboygan

Sheboygan Cottages information

Frequently asked questions