Photo by ed lee schneider

Search Cottages in Sheboygan

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Cottages in Sheboygan

Shoreline Serenity - 2 Private Acres
Dining

Shoreline Serenity - 2 Private Acres

10.0 out of 10, Exceptional, (12)
"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
Fall dates available at SurfDaze!
Property grounds

Fall dates available at SurfDaze!

10.0 out of 10, Exceptional, (105)
"We've been going to this area of Michigan beach for several years as a spring experience and this is our favorite lakefront vrbo. "
Fall dates available at SurfDaze!
On The Rocks. Lake Michigan Beachfront Home.
On the beach, sun loungers, beach towels

On The Rocks. Lake Michigan Beachfront Home.

9.8 out of 10, Exceptional, (7)
On The Rocks. Lake Michigan Beachfront Home.
3-bedroom lake cottage in the Kettle Moraine State Forest
Property grounds

3-bedroom lake cottage in the Kettle Moraine State Forest

9.8 out of 10, Exceptional, (40)
"Stay was excellent."
3-bedroom lake cottage in the Kettle Moraine State Forest
A-frame on Horseshoe Lake
Smart TV

A-frame on Horseshoe Lake

10.0 out of 10, Exceptional, (90)
"Super fun property!"
A-frame on Horseshoe Lake
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
Fall dates and holidays available!
On the beach, sun loungers

Fall dates and holidays available!

10.0 out of 10, Exceptional, (133)
"Lovely "
Fall dates and holidays available!
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, (180)
"Very relaxing."
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Peaceful Cottage on Lake Michigan
Property grounds

Peaceful Cottage on Lake Michigan

10.0 out of 10, Exceptional, (60)
"This cottage is a find!!! The best of the north woods AND the beach. Excellent host!!!"
Peaceful Cottage on Lake Michigan
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Outdoor dining

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 !
Private Beach, Outdoor Dining, Firepit
Property grounds

Private Beach, Outdoor Dining, Firepit

10.0 out of 10, Exceptional, (103)
"Just wanted to get away and relax from the daily stress. This was just what we needed. Secluded and quiet, we were able to just listen to the waves of the lake, read, and walk on the private beach. The cottage was clean and had all the amenities we needed to enjoy our stay. "
Private Beach, Outdoor Dining, Firepit
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Fridge, microwave, oven, stovetop

Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups

2.5 star property
10.0 out of 10, Exceptional, (1)
"It’s a cute place with comfortable beds, clean linens, and plenty of seating. There are lots of windows in the downstairs and the view is great. There are four bedrooms upstairs, and a separate loft area over the garage with the other beds. It’s a great place and will be going back!"
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
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, (15)
"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.
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!
Lakefront Plymouth Cottage w/ Private Hot Tub
Terrace/patio

Lakefront Plymouth Cottage w/ Private Hot Tub

3.0 star property
Lakefront Plymouth Cottage w/ Private Hot Tub
Riverfront Two Rivers Vacation Rental By Beaches
House (2 Bedrooms) | Interior

Riverfront Two Rivers Vacation Rental By Beaches

3.0 star property
8.0 out of 10, Very Good, (1)
"Overall, a very nice property. Updated amenities, comfortable space and right on the river, which was great. Two small frustrations - there were no toiletries in the house (body wash, shampoo, etc) which we have come to expect with rental properties like this. We had to go and buy our own. Second, there were quite a few flies in the house when we got there. We were able to get rid of them but it was a bit of a hassle. "
Riverfront Two Rivers Vacation Rental By Beaches
Family-friendly House: Walk to Lake Michigan!
Microwave, oven, stovetop, dishwasher

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!
Pet-friendly Sheboygan Home, 1 Mi to Lake Michigan
House (4 Bedrooms) | Interior

Pet-friendly Sheboygan Home, 1 Mi to Lake Michigan

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great stay. This is a very nice home. BEAUTIFUL home. Would recommend. Only complaint was lack of electrical outlets. I would recommend and electrician come in and upgrade the home just a bit. OTHER WISE THIS PLACE IS AMAZING WITH TONS OF ROOM!"
Pet-friendly Sheboygan Home, 1 Mi 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.
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

Watershed Hotel

Watershed Hotel

10/10 Excellent
"This hotel is absolutely gorgeous. We loved the modern decor. We enjoyed the breakfast sandwiches. Our room was stunning. We liked how large it was and I appreciated the large handheld mirror. That was a nice, considerate accessory to have in the room. My only complaint was that there wasn't a night stand on both sides of the bed, which was inconvenient as both my husband and I need a nightstand. There was also a billing issue, but they took care of it quickly."
Amy 1-night trip
Posted 6 hours ago
Watershed Hotel

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.
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.