House vacation rentals in Pleasant Prairie

4.93 out of 5 average rating, 101 reviews

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Salem

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch your boat in Center Lake at end of street or visit one of many lakes nearby. Camp Lake less than 2 minutes away, close to Silver Lake and others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Wilmot Mountain, Lake Geneva, & Bristol Renaissance Faire. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base

A spacious living area features a cozy red leather sofa and a patterned rug, while a wooden coffee table sits in the center. A stone fireplace and a lamp provide soft lighting. An open archway leads to a kitchen in the background, with a staircase visible to the side.

4.92 out of 5 average rating, 116 reviews

Outrageous! Near Microsoft Mt Pleasant Sleeps 14

Only a mile from the Legendary Southport Beach of Lake Michigan. Completely Renovated. You will stand in wonder at the homes special features. The upstairs is open to the formal living room. Enjoy the soaring fireplace. Gather in the formal dining room open to the renovated kitchen with breakfast bar. The family will enjoy spreading out in the full size rec room. Three bedrooms and several other sleeping areas will sleep up to 18 people. Fenced yard with furnished patio, grill, and party lights!

The living room is designed with a cozy arrangement of seating, including a sectional sofa and a comfortable chair. A mounted television is positioned above a stone fireplace, with decorative art displayed on the wall and a standing lamp providing soft light.

4.98 out of 5 average rating, 107 reviews

Bright, Airy SuperHost’s Kenosha Backyard Home

Newer, modern 4BR/2.5BA home in peaceful residential neighborhood. 10min from beautiful Kenosha beaches, Microsoft, UWP, Carthage, harbor market, museums, restaurants, & more! The house features 2 dining areas, dedicated office space, and a large unfenced backyard with relaxing patio seating. Very family friendly! Perfect for your family vacation, friends getaway or business trip -we are experienced hosts. Book with confidence! 30min to Milwaukee airport, 50min to O’Hare, 25min to Six Flags

4.98 out of 5 average rating, 232 reviews

A welcoming living area features a comfortable gray couch and a green decorative bench. Light wood flooring extends throughout, with a black coffee table at the center. Large sliding glass doors provide access to the outdoor space, allowing natural light to fill the room.

Home in Beach Park

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.

4.9 out of 5 average rating, 302 reviews

A sunroom is highlighted by large windows adorned with blue fabric shades, allowing ample natural light. Two sizable green palms are positioned in white pots, while a comfortable sofa with decorative cushions provides a relaxing seating area. A patterned area rug adds warmth to the space.

Home in Racine

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!

A charming coastal home is presented with shingle siding and a large covered porch. Lush greenery and flowering plants accentuate the front yard, while a tree stands centrally, framed by the inviting facade of the residence. The pathway leads to the inviting entrance.

4.93 out of 5 average rating, 283 reviews

Hot tub getaway close to Lake Michigan beaches

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

4.95 out of 5 average rating, 129 reviews

Home in Wales

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

4.93 out of 5 average rating, 137 reviews

The modern kitchen features stainless steel appliances, including a refrigerator and stove. Light-colored cabinets provide ample storage, while a window allows natural light to brighten the space. A small table with chairs is positioned against the wall, enhancing functionality.

Home in Waukegan

The Indigo Cottage

This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

4.95 out of 5 average rating, 194 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

A scenic view from the deck showcases a marina filled with moored boats. The backdrop includes lush greenery and a sandy beach area. Strings of decorative lights hang above the deck, and the clear blue sky adds to the inviting atmosphere of the outdoor space.

4.77 out of 5 average rating, 379 reviews

Lake Michigan Paradise Apartment

Private, top floor unit in a duplex on Lake Michigan w/ 900 square feet, 2 bedrooms, 1 large bathroom with shower and soaker tub, open concept living perfect for an amazing getaway. Unobstructed views of Lake Michigan. Relax on your enormous 500 square foot private deck overlooking the lake. Great for fishing. Backyard available for your furry family members. Beach is around the corner. Downtown is a 3 minute walk and has beautiful boutiques, shops, eateries, museums and more!

4.99 out of 5 average rating, 162 reviews

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

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!

A cozy, well-lit living area is visible, featuring a sectional couch and a decorative rug. A small dining table with wooden chairs is positioned near the kitchen, which is subtly accented with shelves displaying glassware. Windows allow natural light to brighten the space.