Holiday houses in Pleasant Prairie

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Top-rated holiday rentals in Pleasant Prairie

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

Guest suite in Zion

4.9 out of 5 average rating, 222 reviews

Nonsmoking, no cleaning fees, mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

Top Guest favourite

Apartment in Kenosha

4.99 out of 5 average rating, 190 reviews

Downtown-Treetop Deck-2Bd/2Bth

Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

Guest favourite

Apartment in Kenosha

4.97 out of 5 average rating, 37 reviews

Blue Sky Landing

Enjoy a comfortable stay at this centrally-located studio.Walking distance to popular restaurants/ taverns, Downtown and Lake Michigan.Separate private entrance for all units. Kitchenette with microwave, airfryer and toaster plus fully stocked cabinets for everything you need to stay in and enjoy meals.Water cooler with hot/cold water and Keurig coffee maker with a selection of premium coffees and teas.Nice size bathroom with shower and jacuzzi bath. Salon quality Shampoo/Conditioner provided

Superhost

Apartment in Racine

4.87 out of 5 average rating, 159 reviews

The Greyhound Apartment

Welcome to The Greyhound, an urban oasis in Downtown Racine. Explore monthly events, dine at local hotspots, or visit cultural landmarks like SC Johnson Frank Lloyd Wright building, Racine Zoo, and more. This professionally designed, newly refurbished apartment features a comfy queen bed, queen sofa sleeper, smart TVs (you can stream from your own accounts) a fully equipped kitchen, and laundry. Bring your canine companion (no cat). Nearby, discover The Graduate Apt for larger groups. Enjoy!

Top Guest favourite

Apartment in Beach Park

4.97 out of 5 average rating, 425 reviews

J’s Farmhouse Cottage. 2 bedroom duplex.

Formerly known as Magnolia Farmhouse inspired. 2 bedroom duplex. Experience the best of the midwest! Enjoy a newly remodeled, "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 miles from Milwaukee, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

Guest favourite

Apartment in Kenosha

4.94 out of 5 average rating, 118 reviews

Kenosha! Work or play, enjoy your stay!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/queen bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

Top Guest favourite

Home in Kenosha

4.99 out of 5 average rating, 84 reviews

6th Ave Harborside

Enjoy all downtown Kenosha has to offer when you stay at this conveniently located cozy and comfortable guest home. Take the bikes downtown to the farmers market, or enjoy the short walk to the beach. Great place to stay if you’re in town for a wedding, bachelorette or bachelor party! Close to the marina & harbor makes it ideal for fishing trips too. Spacious dining room for the whole crew to enjoy a meal together. Enjoy all the comforts of home - reach out for seasonal discounts!

Guest favourite

Guesthouse in Racine

4.9 out of 5 average rating, 241 reviews

Charming log cabin in the woods

This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

Superhost

Home in Kenosha

4.94 out of 5 average rating, 252 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Guest favourite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 310 reviews

Open today! cozy, spacious, comfortable

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Top Guest favourite

Cabin in Kenosha

4.83 out of 5 average rating, 686 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! A true cabin experience. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Two decks overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Guest favourite

Home in Kenosha

4.91 out of 5 average rating, 164 reviews

Beautiful! Near Microsoft Mt Pleasant Sleeps 8

Beautiful three bedroom one and a half bath home. Another stunner by "Homes by Christopher's" Lake Michigan Collection. Completely renovated! Get lost in its charm. This home has a beautifully enclosed porch to relax and enjoy the views. A natural fireplace adds to its ambiance. Plenty of room for the whole family!