Search Cottages in Pleasant Prairie

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Pleasant Prairie

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

A Diamond in the Rough

9.4 out of 10, Exceptional, (89)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

9.6 out of 10, Exceptional, (5)
"Home was very clean, cozy and had everything we needed to make our stay the relaxing getaway we hoped for. Lawn could have been mowed before our arrival so we could have enjoyed the beautiful back yard area more."
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

Powers Lake Home w/ Patio - 9 Mi to Lake Geneva!

3.0 star property
10.0 out of 10, Exceptional, (1)
Powers Lake Home w/ Patio - 9 Mi to Lake Geneva!

Waterfront 2BR Nautical Cottage on Grass Lake - Hot Tub, Firepit & Year-Round Fun

Waterfront 2BR Nautical Cottage on Grass Lake - Hot Tub, Firepit & Year-Round Fun

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
Salem Vacation Home w/ Dock: Steps to Paddock Lake

Lakefront Cottage w/Boat Rentals

10.0 out of 10, Exceptional, (5)
"Host Brian was hands on, took great care of us! Huge picture windows overlooking the lake was amazing. Definitely will return! Thanks Brian!"
Lakefront Cottage w/Boat Rentals

Lakefront Cottage with Gorgeous Sunsets

9.4 out of 10, Exceptional, (6)
"Easy weekend getaway. Cottage is no frills and the porch is a perfect spot to catch a sunset."
Lakefront Cottage with Gorgeous Sunsets

Home on Fox River: Modern Decor Style!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Overall I had a great stay ! "
Home on Fox River: Modern Decor Style!

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

9.6 out of 10, Exceptional, (20)
"Had everything we needed"
Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

Twin Lakes Escape w/ Deck < 1 Mi to Beach!

3.0 star property
Twin Lakes Escape w/ Deck < 1 Mi to Beach!

Powers Lake Gem: Peek-a-Boo Views & Beach Access

Powers Lake Gem: Peek-a-Boo Views & Beach Access

Lakefront Home w/ Game Room, Theater & Dock!

3.0 star property
"Fisherman’s paradise, we caught numerous sizable fish on the dock. Also great for large families or hosting, the house is very well appointed with amenities and entertainment options. Would definitely recommend!"
Lakefront Home w/ Game Room, Theater & Dock!

Lakefront Antioch Home w/ Dock, Kayaks & Game Room

3.0 star property
Lakefront Antioch Home w/ Dock, Kayaks & Game Room

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

10.0 out of 10, Exceptional, (10)
"We enjoyed every minute of our stay! The cottage is very comfortable with awesome views and comfort from both decks. We had a great time fishing, making s’mores and playing games!"
Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Wisconsin Vacation Rental Retreat w/ Deck

3.0 star property
Wisconsin Vacation Rental Retreat w/ Deck

Amazing summer lake escape in our waterfront cottage!!!

9.4 out of 10, Exceptional, (35)
"A perfect place to get away and not have to worry about crowds of people! The boats, the lake and pier access were the best! The owners were so kind to leave my grandkids a huge strong blowup which we tied to the pier and the kids spent hours jumping off into the water! All three of my grandkids caught their first fish right off the pier! We all kayaked for the first time! Highly recommend!"
Amazing summer lake escape in our waterfront cottage!!!

Driftwood, Cozy Waterfront Cottage, Separate Unit

10.0 out of 10, Exceptional, (3)
"Great location. Girls enjoyed the Country Thunder Festival abut 20 minutes away!! I recommend this rental!!"
Driftwood, Cozy Waterfront Cottage, Separate Unit

The Lodge, Sweet Waterfront Cottage, Separate Unit

9.0 out of 10, Wonderful, (6)
"This house is super cute and has a cute, creative layout for a big or small group! My family, friends, and I really enjoyed this rental property. The property manager was very helpful from beginning to end and even left a nice birthday note and some birthday treats, which was above and beyond kind! We would definitely stay here again!"
The Lodge, Sweet Waterfront Cottage, Separate Unit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pleasant Prairie Hotel Reviews

Frequently asked questions

Why book your cottage in Pleasant Prairie with Expedia?
Expedia has some wonderful cottages in Pleasant Prairie, so get ready for a memorable vacation on nature's doorstep. If you're on a budget, select how much you're willing to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a hot tub or free WiFi. We'll help you find a suitable place whatever your style of travel or plans.
How can I find cheap cottages in Pleasant Prairie?
The best way to spot cheap cottages in Pleasant Prairie is with Expedia's convenient filter tool. Narrow your search results by amenities, budget and star rating to access unbeatable bargains in just a few clicks.