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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 50 Cottages in Sheboygan with updated reviews, rates, and availability.

Surfdaze is still open for the Draft! 1 Hour to Green Bay!
Exterior

Surfdaze is still open for the Draft! 1 Hour to Green Bay!

10.0 out of 10, Exceptional, (99)
"This place was as advertised, the host was quick to answer any questions and provide recommendations. We plan on coming back when the weather is nicer to enjoy the outdoor spaces and the lake "
Surfdaze is still open for the Draft! 1 Hour to Green Bay!
BeachDaze is available for Draft week! 1 hour to Green Bay!
Beach

BeachDaze is available for Draft week! 1 hour to Green Bay!

10.0 out of 10, Exceptional, (126)
"As always Cassie’s rentals are great. The house is cute and comfy with all we needed. The location being on Lake Michigan, is perfect for staying in and enjoying the fireplace on cold days, or walking along the beach. Plenty of parks nearby by for hikes and scenery. Visits to Port Washington and aSheboygan are minutes away with lots of great restaurants and things to do.Cassie is very prompt in replying to messages, and responded immediately when we managed to lock ouselves out one chilly...
BeachDaze is available for Draft week! 1 hour to Green Bay!
Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental
Your view from the house

Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental

10.0 out of 10, Exceptional, (33)
"Stay was excellent."
Lake Cottage pet friendly in Kettle Moraine Forest w/ Optional Boat Rental
A-frame on Horseshoe Lake
Exterior

A-frame on Horseshoe Lake

10.0 out of 10, Exceptional, (82)
"From the moment we walked in this property we knew we would love spending our time here. It is roughly 30 minutes from larger towns which was great. The property itself was clean, cozy, and exactly what we hoped for!"
A-frame on Horseshoe Lake
Lakefront Plymouth Cottage w/ Private Hot Tub
Plymouth Vacation Rental | 2BR | 2BA | Access Only By Stairs | 1,352 Sq Ft

Lakefront Plymouth Cottage w/ Private Hot Tub

9.8 out of 10, Exceptional, (8)
"Great location near the track. Beautiful lake and fall color views."
Lakefront Plymouth Cottage w/ Private Hot Tub
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Sunrise over the lake (May)

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

10.0 out of 10, Exceptional, (164)
"This property was beautiful. Huge private back yard. Private pier. The whole lake/ area is very quiet and relaxing. Definitely not a party lake/ area . It was exactly what we wanted/ needed. "
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )
Bright and Cheerful Lake Front Beach Cottage
Living area

Bright and Cheerful Lake Front Beach Cottage

10.0 out of 10, Exceptional, (4)
"Our family loved waking up right on the lake! The perfect place for a relaxing getaway. "
Bright and Cheerful Lake Front Beach Cottage
East Shore Retreat
Outdoor dining

East Shore Retreat

East Shore Retreat
Private Beach, Outdoor Dining, Firepit
Beach

Private Beach, Outdoor Dining, Firepit

10.0 out of 10, Exceptional, (93)
"We LOVED our stay at the Pond Cottage! The cute old cottage feel and look with plenty of space for everyone to sleep and relax was great! But the outside and beachfront are what seal the deal! The beautiful private beach with amazing water and sand but also the overall privacy of the location was perfect. We enjoyed the beach all days swimming, walking, and paddle boarding. We even ate meals out there because it was just too great to stay away. The girls loved sleeping in the bunk beds and my...
Private Beach, Outdoor Dining, Firepit
Peaceful Cottage on Lake Michigan
Exterior

Peaceful Cottage on Lake Michigan

10.0 out of 10, Exceptional, (51)
"If only we hadn’t chose the coldest weekend this place is FANTASTIC! Cozy quiet and very nicely stocked with things to do. Host(s) are fantastic communicators! Highly recommend! "
Peaceful Cottage on Lake Michigan
Pristine Beach Access, Arcade near Kohler-Andrae
Room

Pristine Beach Access, Arcade near Kohler-Andrae

10.0 out of 10, Exceptional, (12)
"Our annual canoe trip got rained out so we were so happy to find this spot! Hiked Kohler Andrae before checking in and had a great time playing ping pong and arcade games after the rain hit. Everything was great!"
Pristine Beach Access, Arcade near Kohler-Andrae
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
Terrace/patio

Peaceful Lakefront Property ONLY 9.5 miles from Road America !

10.0 out of 10, Exceptional, (4)
"Had a wedding in the area and found this cute cabin only minutes away. Absolutely fantastic! Ashley was great about all communication and a n incredible host. Cabin was exceedingly clean, cute, and comfortable. I would highly recommend this place!"
Peaceful Lakefront Property ONLY 9.5 miles from Road America !
No Cleaning Fee Newer LakeHome. Cedar soaking Hot Tub,King Bd,5min walk to Beach
Cedar Soaking Hot Tub drained and filled between each guest stay.

No Cleaning Fee Newer LakeHome. Cedar soaking Hot Tub,King Bd,5min walk to Beach

10.0 out of 10, Exceptional, (16)
"This property was clean, stocked with everything you need and the host was very accommodating! We brought our 9 yr old and 1 year old to visit family for the holiday and the host personally brought over baby toys and a crib for us and had it set up for us when we got there. Happy we found this place and will stay again. "
No Cleaning Fee Newer LakeHome. Cedar soaking Hot Tub,King Bd,5min walk to Beach
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Campbellsport Vacation Rental | 3BR | 1BA | 1,140 Sq Ft | 1 Exterior Step

Colorful Cottage w/ Hot Tub - Steps to Long Lake!

9.4 out of 10, Exceptional, (3)
"Just what we wanted and expected."
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Family-friendly House: Walk to Lake Michigan!
Living area

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: 4 Mi to Lake Michigan
Property grounds

Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan

3.0 star property
Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan
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
Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲
Exterior

Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲

10.0 out of 10, Exceptional, (12)
"Cute little house across from the beach. Perfect for biking and beaching."
Lakeview cottage,88 ft to Lake Michigan, 2 bikes🚲
Updated Plymouth Home ~ 5 Mi to Road America!
Living area

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!
Riverfront Two Rivers Vacation Rental By Beaches
Living area

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
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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Other property types in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Exterior

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (890)
"Beauty place excellent food options better than most"
The price is SAR 323
SAR 367 total
includes taxes & fees
24 Feb - 25 Feb
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Rear deck, yard and Lake Michigan view!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (235)
"The house wasn't quite as clean as advertised. (I took photos.) Tracks on the floor, stuff in sink. Needed blankets in living room! Biggest issue is lack of communication. The locks were due to be changed after we checked out. We were not told until we were locked out of the house. After over an hour we were able to get back in, but the whole experience was unnecessarily stressful. If Mark is willing to give us a partial refund, we'd like to stay at the property again. My partner loved it, aside...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
Property grounds

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (146)
"Great place"
REMODELED HOME ON 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.

Frequently asked questions

How much do cottages in Sheboygan cost?
Cottages in Sheboygan range between and per night. These stays offer a chance to touch base with nature — at a price you can afford. 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?
Reserving a cottage in Sheboygan is as easy as deciding on your travel dates and selecting an ideal place for a vacation in the outdoors. From luxurious retreats to low-cost stays and cottages that have perks like a hot tub, Expedia has something for all styles and tastes. As for terrific deals? We’ve got you covered!
How can I find cheap cottages in Sheboygan?
Expedia is here to help you look for cheap cottages in Sheboygan. To lock in your perfect stay in a couple of clicks, use our handy filter tool to refine your search by amenities, budget and star rating.