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Compare 49 Cottages in Sheboygan with updated reviews, rates, and availability.

Winter dates still available at Surfdaze!
Interior detail

Winter dates still available at Surfdaze!

10.0 out of 10, Exceptional, (95)
"The house was as advertised. We loved the view of the lake and listening to the waves crash. It was a very relaxing stay. We wish we had a few more days!"
Winter dates still available at Surfdaze!
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
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) )
Winter dates still available at Beachdaze!
Interior

Winter dates still available at Beachdaze!

10.0 out of 10, Exceptional, (124)
"We had such a wonderful time! The home was just perfect for the 4 of us- and with unexpected summer weather during a short fall weekend. The views and beach were incredible! It was so comfortable and clean, and had all the necessities and some extras. We look forward to coming back!"
Winter dates still available at Beachdaze!
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
The Pond Cottage - Lake Front on Beautiful Lake Michigan
Beach

The Pond Cottage - Lake Front on Beautiful Lake Michigan

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...
The Pond Cottage - Lake Front on Beautiful Lake Michigan
Pristine Beach Access, Arcade near Kohler-Andrae
Room

Pristine Beach Access, Arcade near Kohler-Andrae

10.0 out of 10, Exceptional, (12)
"We met our extended family here for a long weekend stay on the beach in August. We had a range of kiddos at the VRBO from 3 years to 13. They all loved staying here, playing arcade and ping pong and hanging out with their cousins. Everyone was sad to leave the beach and this amazing home. Thanks for great amenities and an awesome layout for everyone to have fun. "
Pristine Beach Access, Arcade near Kohler-Andrae
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
Bright and Cheerful Lake Front Beach Cottage
Living area

Bright and Cheerful Lake Front Beach Cottage

10.0 out of 10, Exceptional, (4)
"Have stayed here multiple times now and love it every time. Great little place to just stay and relax. Swim. Walk the beach. You can walk for miles! We cook all meals there. We stop at the grocery in oostburg and then the bakery and just hunker down for a relaxing few days. Lovely."
Bright and Cheerful Lake Front Beach Cottage
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, (15)
"The hosts sent welcoming messages and responded quickly to our questions. We had few questions, however, because the hosts had very thoughtfully designed and furnished this lovely property. It’s a gem!"
No Cleaning Fee Newer LakeHome. Cedar soaking Hot Tub,King Bd,5min walk to Beach
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
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🚲
Dog-friendly Sheboygan Home - 1 Mi to Town!
Living area

Dog-friendly Sheboygan Home - 1 Mi to Town!

3.0 star property
Dog-friendly Sheboygan Home - 1 Mi to Town!
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, 1 Mi to Lake Michigan
Living area

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
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
'ania's Retreat' w/ Deck: Walk to Lake Michigan!
Terrace/patio

'ania's Retreat' w/ Deck: Walk to Lake Michigan!

3.0 star property
'ania's Retreat' w/ Deck: Walk to Lake Michigan!
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
Cottage in Campbellsport
Property grounds

Cottage in Campbellsport

Cottage in Campbellsport
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, (873)
"It was beautiful and clean. The front desk lady was very nice and helped so much. "
The price is AED 381
AED 433 total
includes taxes & fees
29 Dec - 30 Dec
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, (232)
"Great stay. Great location. Easy communication. "
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.