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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Guest favourite

Home in Racine

4.91 out of 5 average rating, 217 reviews

“Rustic Farmhouse Retreat” at a working farm

A charming little farmhouse filled with antiques & eclectic artwork from all over the world. It is situated in the middle of a working farm that raises a plethora of exotic fruits, vegetables, shiitake mushrooms, and flowers for local gourmet restaurants. The house interior has a unique design decorated with beautiful hand crafted stonework accented with exotic driftwood trim from old wooden shipwrecks. Try our outdoor Neapolitan wood fired oven for the best pizza ever. A truly unique getaway!

22–29 Sep

$274 NZD per night

Guest favourite

Condo in Kenosha

4.93 out of 5 average rating, 172 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

22–29 May

$171 NZD per night

Guest favourite

Apartment in Kenosha

4.92 out of 5 average rating, 213 reviews

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

8–15 Oct

$199 NZD per night

Guest favourite

Home in Beach Park

4.98 out of 5 average rating, 161 reviews

B’s Farmhouse Cottage 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, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

5–12 Sep

$261 NZD per night

Guest favourite

Apartment in Kenosha

4.98 out of 5 average rating, 217 reviews

Kenosha! Enjoy your stay as you work or play!

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/king 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!

8–15 Dec

$255 NZD per night

Guest favourite

Guest suite in Zion

4.89 out of 5 average rating, 138 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 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 7PM.

14–21 May

$148 NZD per night

Guest favourite

Guesthouse in Racine

4.9 out of 5 average rating, 189 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.

18–25 Jul

$192 NZD per night

Guest favourite

Home in Kenosha

4.97 out of 5 average rating, 197 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.

30 Jan – 6 Feb

$272 NZD per night

Guest favourite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 227 reviews

Love my guests! Homey Elegant & Lake Michigan!

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.

27 Sep – 4 Oct

$162 NZD per night

Guest favourite

Apartment in Elkhorn

4.95 out of 5 average rating, 330 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

28 Dec – 4 Jan

$180 NZD per night

Guest favourite

Apartment in Kenosha

4.98 out of 5 average rating, 114 reviews

Downtown-Treetop Deck-2Bd/2Bth

This one-of-a-kind, shabby-chic second floor apartment is in the heart of Downtown Kenosha, walking distance to coffee shops, restaurants, museums, and Lake Michigan beaches. Enjoy the large, completely secluded back deck equipped to grill, dine, and relax tucked amongst neighborhood buildings with a tree top view. The apartment is great for a romantic rendezvous, a girlfriend getaway, or for an extended stay.

20–27 Dec

$269 NZD per night

Guest favourite

Cabin in Kenosha

4.81 out of 5 average rating, 534 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. 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. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

7–14 Dec

$224 NZD per night