Pleasant Prairie Holiday Rentals

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Holiday Rentals in Pleasant Prairie

Modern Lakeside Villa

10.0 out of 10, Exceptional, (19)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

10.0 out of 10, Exceptional, (3)
"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Tiny Home Retreat with hot tub

8.0 out of 10, Very good, (2)
"We had the most wonderful time"
The price is AU$470
includes taxes & fees
20 Aug - 21 Aug
Tiny Home Retreat with hot tub

New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

10.0 out of 10, Exceptional, (2)
"We were there for a horse show and it was the perfect place after a long day at the show. "
New Listing!! Cozy Lake Shangri-La Cottage!! Big yard, fire pit, sleeps 4

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (14)
"The house, yard and location were all perfect. "
The price is AU$770
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom house in Grayslake

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
The price is AU$2,733
includes taxes & fees
27 Aug - 28 Aug
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

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

9.4 out of 10, Exceptional, (105)
"We had a great stay at the lakehouse! The property was super nice—clean, cozy, and exactly as described. The owner was very communicative and made the entire process smooth. Overall, it was a really good experience. "
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

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

9.8 out of 10, Exceptional, (209)
"Great place to stay! "
The price is AU$1,397
includes taxes & fees
2 Sept - 3 Sept
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (44)
"This is a super fun place to stay! The marina has excellent amenities and the boat was clean and well appointed."
The price is AU$373
includes taxes & fees
27 Aug - 28 Aug
Marina Life II - 28 Carver @ Reef Point Marina

The Randolph Hotel Apt 201

6.0 out of 10, (2)
"Staying in the Round Lake Beach area to visiting family. Room is great and clean. Pretty view of Fox Lake. Only draw back is it is over a bar. Karaoke comes right up through the floor. Not to much of a problem as the bar closes at 11:00. So just have to suffer through the drunken super star want a be singers. It is good for some laughs. Over all I would recommend this place in a heartbeat. "
The price is AU$524
includes taxes & fees
9 Sept - 10 Sept
The Randolph Hotel Apt 201

Large Group Retreat w/ secluded party room and private pool

8.4 out of 10, Very good, (19)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
Large Group Retreat w/ secluded party room and private pool

Rustic Riverside A-Frame Retreat: Secluded Charm.

10.0 out of 10, Exceptional, (15)
"Happy Place, immaculate, well designed, nice mattress, fun easy place with friends"
Rustic Riverside A-Frame Retreat: Secluded Charm.

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.

Beach Lake Michigan King Bed Pet Friendly

9.0 out of 10, Wonderful, (7)
"Judy's townhouse was a perfect spot for us to visit our family in Kenosha. We were all able to gather here to visit and enjoy the beautiful lakefront setting! "
Beach Lake Michigan King Bed Pet Friendly

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (88)
"One of my favorite places I've stayed at "
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (11)
"The space of the house was great. Didnt use any of the big back yard. Had a lot of loud music the last two nights. Kept us awake . Even heard with earplugs."
Entire Beautiful Grove Home

Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table

10.0 out of 10, Exceptional, (4)
"We stayed for two nights and absolutely loved it! The space was cozy and welcoming, and my family felt right at home. The second-floor patio was stunning—we spent both days out there just soaking it all in. The kitchen was beautiful and had everything we needed. Overall, such a wonderful experience and we’d love to come back!"
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table

Twin Lakes Rental One Block from Lake Elizabeth

9.6 out of 10, Exceptional, (30)
"We had a blast at Marks place. It’s just a short walk to a secluded beach and nearby all the fun stuff in town. The host was so accessible and welcoming. The cottage was well- appointed and very comfortable."
Twin Lakes Rental One Block from Lake Elizabeth
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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Top Pleasant Prairie Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Pleasant Prairie?

Yes, there are holiday rentals in Pleasant Prairie close to Jelly Belly Center, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Pleasant Prairie. Make sure you have time to check out the lake views and temples during your trip.

What are some of the best holiday rentals that Pleasant Prairie has to offer?

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar: This holiday home rental outside of Pleasant Prairie offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Pleasant Prairie?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Pleasant Prairie stay.

What can I see and do in Pleasant Prairie?

Lake Michigan and North Point Marina Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jelly Belly Center. In the wider area, you’ll find popular places such as Naval Base Great Lakes and Six Flags Great America.

What are holiday rentals like in Pleasant Prairie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Prairie. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.