A lighthouse at sunset with a colorful sky and calm water.

Search Sheboygan Cottages

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Sheboygan cottages

A two-story house with a front yard and a birdhouse.

1. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
$377 nightly
The price is $397
Sep 20 - Sep 21
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
A porch with two white Adirondack chairs and a wooden railing.

2. Pet Friendly! Steps to Beach - ‘Lakeview Cottage’

Pet Friendly! Steps to Beach - ‘Lakeview Cottage’
Two Rivers
9.0 out of 10, Wonderful, (2 reviews)
"Very clean and beautiful spot."
United States
Jessica B.
$455 nightly
The price is $516
Sep 7 - Sep 8
Total with taxes and fees
Pet Friendly! Steps to Beach - ‘Lakeview Cottage’
A porch with two white Adirondack chairs and a wooden railing.

3. Steps to Beach - Two Rivers Lakeview Cottage

Steps to Beach - Two Rivers Lakeview Cottage
3.0 star property
Two Rivers
$444 nightly
The price is $503
Sep 7 - Sep 8
Total with taxes and fees
Steps to Beach - Two Rivers Lakeview Cottage
A suburban street with houses, a gas station, and a clear sky.

4. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
3.0 star property
Two Rivers
$423 nightly
The price is $476
Sep 7 - Sep 8
Total with taxes and fees
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A two-story house with a front porch, a mailbox, and a small garden with pink flowers.

5. 3 Mi to Road America: Spacious Elkhart Lake Home!

3 Mi to Road America: Spacious Elkhart Lake Home!
3.0 star property
Elkhart Lake
$715 nightly
The price is $804
Sep 7 - Sep 8
Total with taxes and fees
3 Mi to Road America: Spacious Elkhart Lake Home!
A brick house with a chimney, a front porch, and a well-maintained garden.

6. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (58 reviews)
"Great communication and easy check in and check out. Would definitely recommend!"
United States
Jocelyn S.
$454 nightly
The price is $522
Sep 8 - Sep 9
Total with taxes and fees
Charming cottage on Lake Winnebago
A patio with a table and chairs, a bench, and a view of a lake.

7. Waterfront Algoma Vacation Rental on Lake Michigan

Waterfront Algoma Vacation Rental on Lake Michigan
3.0 star property
Algoma
10.0 out of 10, Exceptional, (1 review)
"Its a perfect place to stay inside out. Beautiful rooms, well equipped kitchen and a stunning backyard. We thoroughly enjoyed our stay at this place. Do not miss the perfect sunrise and full moon views from the backyard. Its altogether memorable experience to stay in this place."
United States
Shashi
$450 nightly
The price is $475
Sep 14 - Sep 15
Total with taxes and fees
Waterfront Algoma Vacation Rental on Lake Michigan
A two-story house with a front porch, a garage, and a well-maintained lawn.

8. Walkable Thiensville Retreat Near Hiking!

Walkable Thiensville Retreat Near Hiking!
3.0 star property
Thiensville
$487 nightly
The price is $514
Sep 20 - Sep 21
Total with taxes and fees
Walkable Thiensville Retreat Near Hiking!
A wooden deck with a glass railing overlooking a snowy landscape with trees.

9. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
3.0 star property
Hubertus
$732 nightly
The price is $772
Sep 7 - Sep 8
Total with taxes and fees
Eclectic Hubertus Home w/ Game Room & Fire Pit!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheboygan Hotel Reviews

Harbor Winds Hotel

Harbor Winds Hotel

10/10 Excellent
"Super cute hotel on the river. Staff was very friendly too. Was pleasantly surprised for the price and would come back again."
Nichole 1-night trip
Posted 4 hours ago
Harbor Winds Hotel

Find out more about Sheboygan

Sheboygan Cottages information

Number of reviews
64
Accommodation
74 Cottages
Lowest Price
$397
Highest Price
$804

Frequently asked questions

How much do cottages in Sheboygan cost?
Prices for cottages in Sheboygan range between $397 and $804 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 Harbor Resort & Conference Center Water Park and Whistling Straits Golf Course. John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts and Above & Beyond Children's Museum are also visitor favorites.

Explore a world of travel with Expedia