Book Holiday Homes in Pleasant Prairie

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Featured Holiday Homes in Pleasant Prairie

3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan

Racine
The price is AU$346 per night from 16 Mar to 17 Mar
AU$346
includes taxes & fees
16 Mar - 17 Mar
With a stay at this vacation home in Racine, you'll be within a 10-minute walk of Lake Michigan and North Beach Park.
3-bedroom vacation home just a short walk to Lake Michigan
Enjoy Spectacular Sunset Views ☀️ On True Lakefront

Enjoy Spectacular Sunset Views ☀️ On True Lakefront

Fox Lake
With a stay at this vacation home in Fox Lake, you'll be on the waterfront, within a 15-minute drive of Volo Auto Museum and Jet Funn.
Enjoy Spectacular Sunset Views ☀️ On True Lakefront
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

Caledonia
The price is AU$770 per night from 11 Mar to 12 Mar
AU$770
includes taxes & fees
11 Mar - 12 Mar
With a stay at this vacation home in Caledonia, you'll be on the beach, within a 15-minute drive of Lake Michigan and Ascension SE Wisconsin Hospital - Franklin ...
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
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The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Kenosha
When you stay at this vacation home in Kenosha, you'll be on the waterfront, just steps from Lake Michigan and a 3-minute drive from Carthage College.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

Mundelein
The price is AU$497 per night from 15 Mar to 16 Mar
AU$497
includes taxes & fees
15 Mar - 16 Mar
With a stay at this vacation home in Mundelein, you'll be within a 15-minute drive of Naval Base Great Lakes and Pine Meadow Golf Club.
Quaint Bungalow, near Great Lakes Naval Base
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Richmond
When you a stay at this vacation home in Richmond, you'll be next to a golf course, just steps from Lake Elizabeth and Elizabeth Lake Nature Preserve.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
New Your Home Away From Home! - Near Great Lakes Naval Base!!

New Your Home Away From Home! - Near Great Lakes Naval Base!!

North Chicago
When you stay at this vacation home in North Chicago, you'll be on a lake, within a 5-minute drive of Naval Base Great Lakes and Lake Michigan.
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach

Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach

Burlington
With a stay at this vacation home, you'll be centrally located in Burlington, within a 10-minute drive of Spinning Top and Yo-Yo Museum and Logic Puzzle ...
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach
Family frndly TwnHm by navy base

Family frndly TwnHm by navy base

2 out of 5
Waukegan
With a stay at this vacation home in Waukegan, you'll be a 2-minute drive from Lake Michigan and 7 minutes from Naval Base Great Lakes.
Family frndly TwnHm by navy base
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pleasant Prairie Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Pleasant Prairie vacation homes are the perfect way for you to wing it.

Holiday houses in Pleasant Prairie let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Pleasant Prairie in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Pleasant Prairie adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pleasant Prairie with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Pleasant Prairie vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Pleasant Prairie Holiday Homes essential information

Accommodation
275 Holiday Homes
Lowest Price
AU$96
Highest Price
AU$770
Popular accommodation
3-bedroom vacation home just a short walk to Lake Michigan, Enjoy Spectacular Sunset Views ☀️ On True Lakefront, 7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool, The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft, Quaint Bungalow, near Great Lakes Naval Base, 🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲, New Your Home Away From Home! - Near Great Lakes Naval Base!!, Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach, Family frndly TwnHm by navy base

Top trending hotels in Pleasant Prairie

Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
7540 118th Ave, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 12 Mar to 13 Mar
AU$130
includes taxes & fees
12 Mar - 13 Mar
With a stay at Days Inn by Wyndham Pleasant Prairie Kenosha in Pleasant Prairie, you'll be near the airport, within a 15-minute drive of Lake Michigan and America's ...
Days Inn by Wyndham Pleasant Prairie Kenosha
Doubletree by Hilton Pleasant Prairie Kenosha

Doubletree by Hilton Pleasant Prairie Kenosha

4 out of 5
11800 108th St, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 23 Mar to 24 Mar
AU$197
includes taxes & fees
23 Mar - 24 Mar
Located in Pleasant Prairie, Doubletree by Hilton Pleasant Prairie Kenosha is in a shopping district, a 3-minute walk from Pleasant Prairie Premium Outlets and ...
Doubletree by Hilton Pleasant Prairie Kenosha
Super 8 by Wyndham Kenosha/Pleasant Prairie

Super 8 by Wyndham Kenosha/Pleasant Prairie

2 out of 5
7601 118th Ave, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is AU$96 per night from 23 Mar to 24 Mar
AU$96
includes taxes & fees
23 Mar - 24 Mar
With a stay at Super 8 by Wyndham Kenosha/Pleasant Prairie, you'll be centrally located in Pleasant Prairie, within a 15-minute drive of Lake Michigan and America's ...
Super 8 by Wyndham Kenosha/Pleasant Prairie
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Fairfield Inn & Suites Kenosha Pleasant Prairie

Fairfield Inn & Suites Kenosha Pleasant Prairie

2.5 out of 5
10601 120TH AVENUE, Pleasant Prairie, WI
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 23 Mar to 24 Mar
AU$168
includes taxes & fees
23 Mar - 24 Mar
With a stay at Fairfield Inn & Suites Kenosha Pleasant Prairie in Pleasant Prairie, you'll be a 3-minute walk from Pleasant Prairie Premium Outlets and within ...
Fairfield Inn & Suites Kenosha Pleasant Prairie
Don't see what you're looking for?
See all available properties in Pleasant Prairie
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.