
Holiday houses in Pleasant Prairie
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pleasant Prairie
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Pleasant Prairie
Superhost

Home in Fox Lake
4.76 out of 5 average rating, 29 reviewsPistakee Lake Getaway
JaniceRating, 5 stars3 months ago
Zach was very responsive and helpful with our last minute planning. The property is exactly as indicated in the photos and was very clean. Even in the winter, the lake view was exactly what we needed … very relaxing and the location is close to shopping and restaurants. Thank you, Zach, for all your help! one thing that has nothing to do with the host or the house itself … google maps has a difficult time routing you to this property … Waze is a better option. Getting to the property by turning on Gibson from the main road is a much better option and provides a more clear route. You won’t regret a stay at this property!
Guest favourite

Guest suite in Wind Lake
4.85 out of 5 average rating, 20 reviewsSecret Garden Getaway
CassidyRating, 5 stars7 months ago
Sandy was such an amazing host! She was very kind and respectful. The place was beautiful! We went for a wedding and found that the location of the Airbnb was right around the corner, super convenient and so peaceful.
Superhost

Home in Fox Lake
4.89 out of 5 average rating, 54 reviewsStunning Lake Views, Huge Deck, Water Fun!
KymRating, 5 stars2 months ago
Absolutely Loved our stay!! There aren't enough good things to say about the view, location & beautiful house. So fun! There's a pool table, air hockey & 2 free standing video games. Spent every sunset in the Lakeview room😍 Just gorgeous beyond words! Did i mention the Bald Eagle that hangs out in the tree right outside the Lakeview bedroom? Incredible! the lake doesn't freeze over in one spot in front of the lakeview window, saw all the big birds of prey hunt. It was definitely wildlife at its finest. The owners are Very responsive & told us to be on the look out for the eagle! Fantastic time! Loved Loved Loved it & already reserved for our Wedding weekend❤️
Guest favourite

Home in North Chicago
5 out of 5 average rating, 17 reviewsJ&J Vacay 2 story
AmyRating, 5 stars2 weeks ago
Great location near base if you are coming for graduation. Lots of room. Bring your own soap/shampoo for bathrooms.
Superhost

Home in West Allis
4.77 out of 5 average rating, 153 reviews★Cozy Beach Themed Home★2 Beds★Spacious Parking★
HélèneRating, 5 stars1 month ago
Tiare’s place was per the description and comfortable. The driveway was well shoveled/cleared after the snow. Place is conveniently located for our trip purpose.
Guest favourite

Home in Antioch
4.92 out of 5 average rating, 114 reviewsEntertain on The Chain! water sports and sauna.
JasonRating, 5 stars4 months ago
Wonderful place to stay, even in cold weather like we encountered over Thanksgiving. The house is spacious enough for multiple people to have their own space or enjoy the large living room area together. Very enjoyable!
Guest favourite

Home in Lake Geneva
4.91 out of 5 average rating, 110 reviewsLake Geneva cottage with private beach access
ShaeRating, 5 stars1 week ago
The place was very cute and clean , well decorated and in a great location. Jennifer and Angela were very responsive and friendly. Would definitely stay again !
Guest favourite

Cottage in Wonder Lake
4.92 out of 5 average rating, 133 reviewsThe Cozy Lake House/ Perfect Winter Getaway!DM ?s
DeniseRating, 5 stars3 weeks ago
Steve was an excellent host! Had no idea what to expect considering this was my First Airbnb experience. From the moment we walked in I loved the house & how well furnished & detailed it was. They had everything thought out. From all the kitchen appliances one may need, activities to do in house, to blankets and firewood to bond over the fire pit outside. The property plus amenities made us feel like home. Neighbors were so kind! Our dogs were so relaxed as were we. Steve was extremely helpful & attentive. Ran short on a few essentials and Steve immediately took care of things. Also gave great recommendations of restaurants & nearby parks to walk/hike. Property is also close to many nearby stores if you need any extra produce. Can’t wait to book my next stay here, would 100% recommend Steve’s spot. Can genuinely say I had a great first experience.
Quick stats about holiday rentals in Pleasant Prairie
Total rentals
30 properties
Nightly prices starting at
$84 AUD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
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- Millennium Park
- Wrigley Field
- United Center
- Milwaukee Public Museum
- Wilmot Mountain Ski Resort
- Navy Pier
- Racine North Beach
- Frank Lloyd Wright Home and Studio
- Grand Geneva Resort & Spa
- Lincoln Park Zoo
- Illinois Beach State Park
- Chicago History Museum
- Geneva National Resort & Club
- 875 North Michigan Avenue
- Alpine Valley Resort
- Skydeck Chicago
- Butler National Golf Club
- Otter Cove Aquatic Park
- Chicago Golf Club
- Villa Olivia
- Medinah Country Club
- The Water Works Indoor Water Park
- Pirates' Cove Children's Theme Park
- The Oasis Water Park