Compare Sheboygan Cottage Rentals

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Featured Sheboygan Cottages

Shoreline Serenity - 2 Private Acres

Shoreline Serenity - 2 Private Acres

Cleveland WI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
On The Rocks. Lake Michigan Beachfront Home.

On The Rocks. Lake Michigan Beachfront Home.

Cedar Grove WI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
3-bedroom lake cottage in the Kettle Moraine State Forest

3-bedroom lake cottage in the Kettle Moraine State Forest

Campbellsport WI
Guests staying at this cottage can enjoy a gym, barbecue grills, and a water dispenser. This cottage also has a garden.
Kitchen
Pet friendly
Winter's a good time to stay in & cuddle at Surfdaze

Winter's a good time to stay in & cuddle at Surfdaze

Oostburg WI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) )

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

Kiel WI
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Cozy Crystal Lakefront Cottage

Cozy Crystal Lakefront Cottage

3 out of 5
Plymouth WI
Guests staying at this cottage have access to local meal delivery service, barbecue grills, and a garden.
Kitchen
Washer
Peaceful Cottage on Lake Michigan

Peaceful Cottage on Lake Michigan

Two Rivers WI
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Air conditioning
2 Mi to Lincoln Park Zoo: Family-friendly Home

2 Mi to Lincoln Park Zoo: Family-friendly Home

3 out of 5
Manitowoc WI
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive.
Kitchen
Washer
Lake Breeze Cottage. One block from the lake, walking distance to downtown!

Lake Breeze Cottage. One block from the lake, walking distance to downtown!

Sheboygan WI
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
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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.

Sheboygan Beach Accommodation

    Harbor Winds Hotel

    Harbor Winds Hotel

    905 S 8th St Sheboygan WI
    $70 nightly
    The price is $80 total per night from Dec 31 to Jan 1
    $80 total
    Dec 31 - Jan 1, 2026
    Total with taxes and fees
    8.4/10 Very Good! (931 reviews)

Hotel Options in Sheboygan

    Grandstay Residential Suites Hotel - Sheboygan

    Grandstay Residential Suites Hotel - Sheboygan

    708 Niagara Avenue Sheboygan WI
    $125 nightly
    The price is $142 total per night from Dec 28 to Dec 29
    $142 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.6/10 Excellent! (1,013 reviews)
    Watershed Hotel

    Watershed Hotel

    838 N 15th St Sheboygan WI
    $120 nightly
    The price is $136 total per night from Dec 26 to Dec 27
    $136 total
    Dec 26 - Dec 27
    Total with taxes and fees
    9.6/10 Exceptional! (467 reviews)
    AmericInn by Wyndham Sheboygan

    AmericInn by Wyndham Sheboygan

    3664 S Taylor Dr Sheboygan WI
    $68 nightly
    The price is $77 total per night from Dec 31 to Jan 1
    $77 total
    Dec 31 - Jan 1, 2026
    Total with taxes and fees
    8.4/10 Very Good! (1,003 reviews)

Cottages

Book a cottage in Sheboygan
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Sheboygan. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Sheboygan better.

Cottage apartments in Sheboygan range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Sheboygan
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Sheboygan and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Sheboygan cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Sheboygan. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Sheboygan Cottages essential information

Accommodation
70 Cottages
Lowest Price
$77
Highest Price
$142
Popular accommodation
Shoreline Serenity - 2 Private Acres, On The Rocks. Lake Michigan Beachfront Home., 3-bedroom lake cottage in the Kettle Moraine State Forest, Winter's a good time to stay in & cuddle at Surfdaze, Enjoy a relaxing vacation on a lake (1 Bedroom (sleeps 4) ), Cozy Crystal Lakefront Cottage, Peaceful Cottage on Lake Michigan, 2 Mi to Lincoln Park Zoo: Family-friendly Home, Lake Breeze Cottage. One block from the lake, walking distance to downtown!

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