House vacation rentals in Pleasant Prairie

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Top-rated house rentals in Pleasant Prairie

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Guest favorite

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!

Aug 21 – 28

G$30,854 GYD per night

Guest favorite

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.

Dec 21 – 28

G$27,089 GYD per night

Guest favorite

Home in Wales

4.92 out of 5 average rating, 146 reviews

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Jan 16 – 23

G$31,939 GYD per night

Guest favorite

Home in Racine

4.9 out of 5 average rating, 243 reviews

Historic Racine - Lovely Retreat Home - 3B/1.5B

Amazing, authentic, TRUE historic home, built all the way back in 1858! Meticulously maintained and updated over the years while taking care to stay faithful to the original character, this house is a feature on the City of Racine's "Tour of Historic Places". The home features original brick and woodwork, a two story sunroom addition from the 1920's, and a fully fenced backyard with grill, patio, garden and seating. Privacy for the adults to chat; space for the kids and/or dog to roam free!

Oct 24 – 31

G$32,219 GYD per night

Guest favorite

Home in Antioch

4.9 out of 5 average rating, 106 reviews

Lakefront, beautiful views, spacious and private.

Plenty of room for the whole family along with space to sneak away with your favorite book. STUNNING LAKEFRONT RETREAT! Private street with panoramic views of Lake Antioch. Beautiful sunsets, private beach, pier and Kayaks. Outstanding fishing. Walk to downtown's restaurants, bars, shopping, theater and concerts in the park. Enjoy ice fishing and Wilmot/Vail ski resort nearby. Relax with two fireplaces, three TVs, pool table, large wet bar, huge kitchen, eating areas, private office, and gym.

Apr 20 – 27

G$111,719 GYD per night

Guest favorite

Home in Kenosha

4.91 out of 5 average rating, 236 reviews

Coastal Style Estate

Large cottage estate near beaches, dining & Carthage College. 5 BR/4 Baths, a chef's kitchen with Viking & Subzero appliances, large dining area for 12, 2 spacious living rooms for gathering & relaxing. Spacious property, forest views, outdoor spaces for dining, lounging & recreation. The lakefront beaches are walkable under a mile, +harbor, downtown restaurants, shopping & museums are a short drive/bike. Activities include hot tub, fire pit, pickleball, basketball, ping pong & lawn games!

Oct 10 – 17

G$128,090 GYD per night

Superhost

Home in Twin Lakes

4.93 out of 5 average rating, 134 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

Oct 4 – 11

G$116,664 GYD per night

Guest favorite

Home in Ingleside

4.93 out of 5 average rating, 111 reviews

Gorgeous Nautical 2/2 Lake House Chain O' Lakes

Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is an optional 5-6 person hot tub on the back deck for you to relax and unwind (See access and maintenance fee). Fully remodeled modern lake house

Apr 11 – 18

G$42,318 GYD per night

Guest favorite

Home in Round Lake Beach

4.89 out of 5 average rating, 153 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Aug 21 – 28

G$56,894 GYD per night

Guest favorite

Home in Round Lake Beach

4.99 out of 5 average rating, 102 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Dec 8 – 13

G$38,601 GYD per night

Superhost

Home in Fox Lake

4.94 out of 5 average rating, 141 reviews

Beach Bungalow Getaway ★ Chain O Lakes

Outdoor enthusiasts will be delighted with this quaint romantic cottage. Walk down to the lake to enjoy boating, swimming, fishing, and more. The fall colors, hiking, and nature setting is especially breathtaking this time of year. Experience all the comforts of home in this newly remodeled lake cottage desirably located on Lippincott Point. Perfect for gathering with friends by the lakeside fire pit, boating “the chain” and all that lake life has to offer!

Dec 10 – 17

G$34,990 GYD per night

Guest favorite

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.

Mar 6 – 13

G$26,104 GYD per night