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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Featured Cottages in Sheboygan

Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Outdoor dining

Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )

10.0 out of 10, Exceptional, (182)
"Very relaxing."
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Fall dates available at SurfDaze!
Property grounds

Fall dates available at SurfDaze!

10.0 out of 10, Exceptional, (108)
"It was wonderful. Views were stunning. So close to the water. Very relaxing. Our family loved it."
Fall dates available at SurfDaze!
On The Rocks. Lake Michigan Beachfront Home.
Property grounds

On The Rocks. Lake Michigan Beachfront Home.

9.8 out of 10, Exceptional, (9)
On The Rocks. Lake Michigan Beachfront Home.
Shoreline Serenity - 2 Private Acres
Exterior

Shoreline Serenity - 2 Private Acres

9.8 out of 10, Exceptional, (15)
"This place is beautiful. It is decorated with a beachy theme that matches the breathtaking views. The attention to detail was superb and the little extras the owner added made our stay very special."
Shoreline Serenity - 2 Private Acres
October Dates available!
Outdoor dining

October Dates available!

10.0 out of 10, Exceptional, (134)
"Lovely "
October Dates available!
A-frame on Horseshoe Lake
Exterior

A-frame on Horseshoe Lake

10.0 out of 10, Exceptional, (91)
"This property exceeded our expectations. It was beautiful and had everything and more that we needed. The lake access was amazing! "
A-frame on Horseshoe Lake
Cozy Crystal Lakefront Cottage
Terrace/patio

Cozy Crystal Lakefront Cottage

3.0 star property
10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed our stay. We spent most of the time kayaking and paddle boarding. At night we sat around the campfire making smores and played games on the porch. The surrounding area was very beautiful and peaceful. The spacious cottage was as lovely as Pete described it. We would highly recommend it and rent again. Thanks Pete!! Tim"
Cozy Crystal Lakefront Cottage
Peaceful Cottage on Lake Michigan
Property grounds

Peaceful Cottage on Lake Michigan

10.0 out of 10, Exceptional, (62)
"A perfect place to unplug and unwind."
Peaceful Cottage on Lake Michigan
See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.
Exterior

See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.

9.0 out of 10, Wonderful, (16)
"Cute little house across from the beach. Perfect for biking and beaching."
See the Lake! Hear the Waves! Steps to the Beach! Entire cottage. 2 bikes.
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Exterior

Peaceful Lakefront Property ONLY 9.5 miles from Road America !

10.0 out of 10, Exceptional, (5)
"We came to visit family and were so happy with our accomodations. The hosts are so friendly and the cabin felt like home. It all everything we needed and the beach access was a wonderful bonus!"
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
3-bedroom lake cottage in the Kettle Moraine State Forest
Outdoor dining

3-bedroom lake cottage in the Kettle Moraine State Forest

9.8 out of 10, Exceptional, (43)
"Enjoyed our stay. Appreciated the lake rules limited wake time which ensured a relaxing stay,"
3-bedroom lake cottage in the Kettle Moraine State Forest
East Shore Retreat
Outdoor dining

East Shore Retreat

6.0 out of 10, (2)
"Beautiful view and main room. Dishes were dir"
East Shore Retreat
Pristine Beach Access, Arcade near Kohler-Andrae
Exterior

Pristine Beach Access, Arcade near Kohler-Andrae

10.0 out of 10, Exceptional, (21)
"Overall great experience"
Pristine Beach Access, Arcade near Kohler-Andrae
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Property grounds

Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups

2.5 star property
10.0 out of 10, Exceptional, (3)
"The house was clean and fully equipped with everything you need. It feels like a home away from home. There is plenty of space and seating areas so the family can gather. We really enjoyed the large backyard with private access to the lake. The neighbors were extremely friendly which is a big plus, we will definitely plan on staying again in the future."
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Updated Plymouth Home ~ 5 Mi to Road America!
House (3 Bedrooms) | Interior

Updated Plymouth Home ~ 5 Mi to Road America!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful spot, calm and clean neighborhood, close to the track. A real find."
Updated Plymouth Home ~ 5 Mi to Road America!
Steps to Lake Michigan: Manitowoc Home w/ Fire Pit
House (3 Bedrooms) | Interior

Steps to Lake Michigan: Manitowoc Home w/ Fire Pit

3.0 star property
Steps to Lake Michigan: Manitowoc Home w/ Fire Pit
Spacious Recently Built Home < 1 Mi to Lake!
House (3 Bedrooms) | Interior

Spacious Recently Built Home < 1 Mi to Lake!

3.0 star property
Spacious Recently Built Home < 1 Mi to Lake!
Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
House (5 Bedrooms) | Interior

Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!

3.0 star property
Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
Walkable Lake Elkhart Apt: Dine, Shop, Swim!
House (2 Bedrooms) | Interior

Walkable Lake Elkhart Apt: Dine, Shop, Swim!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This apartment is a block from siebkens and the downtown farmers market. Excellent location. Comfortable beds. There are two apartments so if the space in one is not enough consider both "
Walkable Lake Elkhart Apt: Dine, Shop, Swim!
Family-friendly House: Walk to Lake Michigan!
Exterior

Family-friendly House: Walk to Lake Michigan!

3.0 star property
10.0 out of 10, Exceptional, (1)
Family-friendly House: Walk to Lake Michigan!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheboygan Hotel Reviews

Find out more about Sheboygan

Find out more about Sheboygan

Sheboygan Cottages information

Number of reviews
Accommodation
67 Cottages
Lowest Price
Highest Price

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Frequently asked questions

How much do cottages in Sheboygan cost?
Prices for cottages in Sheboygan range between and 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.
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.