Compare Southern Wisconsin Cottage Rentals

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Featured Southern Wisconsin 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
Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach.

Lake Geneva WI
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Washer
Dryer
The Harwood House

The Harwood House

Prairie du Chien WI
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

Baraboo WI
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Little House in the Big Woods on the Prairie

Little House in the Big Woods on the Prairie

Baraboo WI
This cottage features a water park and barbecue grills.
Kitchen
Free WiFi
Williams Bay beach cottage with hot tub on 2-acres

Williams Bay beach cottage with hot tub on 2-acres

Delavan WI
Ski-in/ski-out access, a sauna, and a hot tub are featured at this cottage. Other amenities at this ski cottage include an arcade/game room, laundry facilities, and a garden.
Hot Tub
Kitchen
Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago

Neenah WI
$423 nightly
The price is $486 total per night
$486 total
Dec 19 - Dec 20
Total with taxes and fees
At this cottage, guests have access to an arcade/game room, laundry facilities, 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
Cedarburg \ Mequon River retreat

Cedarburg \ Mequon River retreat

Mequon WI
At this cottage, guests have access to features like laundry facilities.
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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.

Hotel Options in Southern Wisconsin

    The Pfister Hotel

    The Pfister Hotel

    424 E Wisconsin Ave Milwaukee WI
    $169 nightly
    The price is $199 total per night from Jan 5 to Jan 6
    $199 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    9.4/10 Exceptional! (1,800 reviews)
    The Madison Concourse Hotel and Governor's Club

    The Madison Concourse Hotel and Governor's Club

    1 W Dayton St Madison WI
    $139 nightly
    The price is $161 total per night from Dec 21 to Dec 22
    $161 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.4/10 Exceptional! (3,374 reviews)
    Saint Kate - The Arts Hotel

    Saint Kate - The Arts Hotel

    139 E Kilbourn Ave Milwaukee WI
    $128 nightly
    The price is $151 total per night from Dec 28 to Dec 29
    $151 total
    Dec 28 - Dec 29
    Total with taxes and fees
    9.6/10 Exceptional! (2,472 reviews)

Cottages

Book a cottage in Southern Wisconsin
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Southern Wisconsin. 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 Southern Wisconsin better.

Cottage apartments in Southern Wisconsin 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 Southern Wisconsin
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 Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin. 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.

Southern Wisconsin Cottages essential information

Accommodation
73 Cottages
Lowest Price
$151
Highest Price
$486
Popular accommodation
Shoreline Serenity - 2 Private Acres, Quiet 2bd 1ba ranch with off street parkingWalking distance to downtown/beach., The Harwood House, Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake , Little House in the Big Woods on the Prairie, Williams Bay beach cottage with hot tub on 2-acres, Charming cottage on Lake Winnebago, On The Rocks. Lake Michigan Beachfront Home., Cedarburg \ Mequon River retreat

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