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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Browse Select Sheboygan Cottages

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
'ania's Retreat' w/ Deck: Walk to Lake Michigan!
House (3 Bedrooms) | Interior

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

3.0 star property
'ania's Retreat' w/ Deck: Walk to Lake Michigan!
Dog-friendly Sheboygan Home - 1 Mi to Town!
House (1 Bedroom) | Interior

Dog-friendly Sheboygan Home - 1 Mi to Town!

3.0 star property
Dog-friendly Sheboygan Home - 1 Mi to Town!
Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan
House (3 Bedrooms) | Front of property

Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan

3.0 star property
Pet-friendly Sheboygan Home: 4 Mi to Lake Michigan
Lakefront Campbellsport Retreat w/ Dock & Yard!
House (4 Bedrooms) | Interior

Lakefront Campbellsport Retreat w/ Dock & Yard!

3.0 star property
Lakefront Campbellsport Retreat w/ Dock & Yard!
Spacious Sheboygan Home w/ Grill & Fire Pit!
House (5 Bedrooms) | Interior

Spacious Sheboygan Home w/ Grill & Fire Pit!

3.0 star property
Spacious Sheboygan Home w/ Grill & Fire Pit!
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!
2 Mi to Road America: Pet-friendly Duplex!
House (4 Bedrooms) | Interior

2 Mi to Road America: Pet-friendly Duplex!

3.0 star property
2 Mi to Road America: Pet-friendly Duplex!
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Interior

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

3.0 star property
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Near Hiking: Lakefront Getaway in Campbellsport!
House (4 Bedrooms) | Interior

Near Hiking: Lakefront Getaway in Campbellsport!

3.0 star property
Near Hiking: Lakefront Getaway in Campbellsport!
Waterfront Fond du Lac Home on Deneveu Lake!
House (3 Bedrooms) | Interior

Waterfront Fond du Lac Home on Deneveu Lake!

3.0 star property
Waterfront Fond du Lac Home on Deneveu 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!
Walk to Beaches + Restaurants: Elkhart Lake Escape
House (4 Bedrooms) | Interior

Walk to Beaches + Restaurants: Elkhart Lake Escape

3.0 star property
Walk to Beaches + Restaurants: Elkhart Lake Escape
Colorful Cottage w/ Hot Tub - Steps to Long Lake!
Cottage (3 Bedrooms) | Interior

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

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

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent
"Overall stay was good"
Jeffrey 8-night trip
Posted 3 days ago
La Quinta Inn by Wyndham Sheboygan

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?
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