Holiday rentals in Pleasant Prairie

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Top-rated holiday rentals in Pleasant Prairie

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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!

8–15 May

€ 151 per night

Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 26 reviews

Sister House Cottage-Beachy Charm-Driveway Parking

Sister House Cottage is a 1920’s bungalow charmingly furnished in a beachy vintage theme. A restful screened in front porch looks out onto a quiet tree filled, family oriented neighborhood. Enjoy the many lovely beaches in Kenosha with provided beach towels, lawn chairs and sand toys! Just a 5 minute drive to Lake Michigan! 3 blocks from large park with playground, disc golf and garden. To help make your family stay more relaxing we offer a portable crib, stroller and high-chair for your use.

18–25 Aug

€ 168 per night

Guest favourite

Apartment 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.

20–27 May

€ 98 per night

Guest favourite

Flat 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.

7–14 Aug

€ 116 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.

7–14 Apr

€ 147 per night

Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 96 reviews

LITTLE HOUSE by the BIG LAKE

Only steps away from Lake Michigan, our newly renovated home is your southeast Wisconsin retreat. The home is in a peaceful neighborhood, less than 2 blocks from the Eichelman scenic park/beach. Kenosha's downtown which is loaded with fun shops, restaurants, cafes and breweries is a short walk away. Take a stroll to the harbor, lighthouse, Civil War Museum, and marina. 1/2 hour down the lake front to Great Lakes Naval Station. Dates not available? Check out the Cozy Cottage by the Big Lake.

11–18 Oct

€ 239 per night

Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 52 reviews

Tu Casa Cottage - Your Home Away From Home

Recently renovated cozy cottage in a quiet neighborhood approximately 1 mile from downtown Kenosha which features restaurants, shops, wedding venues, marina and multiple beaches on beautiful Lake Michigan. This 1913 charmer has the perfect amount of space for a single person or couple visiting the Kenosha area. Home offers one bed, one bath, living room, separate dinning room, kitchen, theater room and office. Everything in this house is new including the furniture and kitchen appliances!

14–21 Jul

€ 120 per night

Guest favourite

Flat 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!

6–13 Dec

€ 144 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.

2–9 May

€ 80 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.

9–16 Nov

€ 153 per night

Guest favourite

Flat 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.

15–22 Sep

€ 89 per night

Guest favourite

Flat 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.

6–13 Nov

€ 139 per night