Search Cottages in Pleasant Prairie

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
7 Rab. I - 9 Rab. I
In two weeks
14 Rab. I - 16 Rab. I
In one month
28 Rab. I - 30 Rab. I
In two months
25 Rab. II - 27 Rab. II

Compare 42 Cottages in Pleasant Prairie with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (65)
"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Beach nearby

White House, Amazing Cottage, Lake Front, That Sleeps 34!

9.2 out of 10, Wonderful, (9)
"We had an amazing stay with our family group of 30 people! The place is perfectly equipped for a large group, with plenty of kitchen utensils, beds, towels, sheets, and blankets—everything we needed for a comfortable stay. The view is absolutely breathtaking, and the area is so peaceful. We loved every moment and would highly recommend it to anyone looking for a great place for a big family gathering!"
White House, Amazing Cottage, Lake Front, That Sleeps 34!
Lakefront Cottage with Gorgeous Sunsets
Pool

Lakefront Cottage with Gorgeous Sunsets

9.4 out of 10, Exceptional, (6)
"Beautiful area. Warm and cozy place."
Lakefront Cottage with Gorgeous Sunsets
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
TV, fireplace, books

6 Mi to Naval Base: Spacious Waukegan Home w/ Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
6 Mi to Naval Base: Spacious Waukegan Home w/ Yard
A Diamond in the Rough
Sun loungers

A Diamond in the Rough

9.4 out of 10, Exceptional, (85)
"Very cosy & nice. The backyard was wonderful. We enjoyed the privacy. The location was convenient to restaurants, etc."
A Diamond in the Rough
Updated Twin Lakes Cottage, Walk to Lake Mary
Interior

Updated Twin Lakes Cottage, Walk to Lake Mary

9.6 out of 10, Exceptional, (35)
"We loved our Little Blue House! Everything felt cozy, even the backyard and driveway, it was so convenient. It’s clean and safe and cute. What an amazing Stay- The people are nice, food was GREAT, and this is a great location from Wilmot. "
Updated Twin Lakes Cottage, Walk to Lake Mary
The Lodge, Sweet Waterfront Cottage, Separate Unit
Beach nearby

The Lodge, Sweet Waterfront Cottage, Separate Unit

9.2 out of 10, Wonderful, (5)
"House is a duplex with common wall and deck area."
The Lodge, Sweet Waterfront Cottage, Separate Unit
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Terrace/patio

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

10.0 out of 10, Exceptional, (8)
"Homey and comfortable- the house had everything we needed with a nice, large kitchen. Everything was exactly as pictured. Right on the water with so much outdoor space! We had plenty of space to spread out inside-and the bar area and game room was a fun bonus. The sunsets were gorgeous and we enjoyed watching the eagles fly overhead. Close to shopping and restaurants. Would rent again!"
Waterfront Fox Lake Vacation Rental w/ Fire Pit!
Twin Lakes Cottage: Walk to Elizabeth Lake!
TV, DVD player, books, video library

Twin Lakes Cottage: Walk to Elizabeth Lake!

9.2 out of 10, Wonderful, (10)
"Three of us senior gals stayed at Twin Lakes Cottage for 3 nights. It is a delightful place! It’s obvious that Pam and her brother love being hostess and host and were quick to respond to the littlest request. They were helpful with info on the area, places to see and eat. The cottage was clean and neat. Good beds. Pam has had fun filling (not overfilling!) the cottage with vintage items. A walk-in pantry was a delight to find. Plenty of kitchen items. Plenty of pillows and blankets. Pleasant...
Twin Lakes Cottage: Walk to Elizabeth Lake!
Driftwood, Cozy Waterfront Cottage, Separate Unit
Beach nearby

Driftwood, Cozy Waterfront Cottage, Separate Unit

10.0 out of 10, Exceptional, (2)
"We loved everything about this property and it was perfect for our family vacation. This house was wonderfully stocked with everything we needed in the kitchen, bathroom, and bedrooms. We had a large group, but with the big backyard space that overlooked the lake, we fit very comfortably. Check in was easy and any questions I asked were answered promptly. We would highly recommend staying in this cute, updated home for your next lake getaway!"
Driftwood, Cozy Waterfront Cottage, Separate Unit
Lakefront cottage with gorgeous sunset views
Property grounds

Lakefront cottage with gorgeous sunset views

Lakefront cottage with gorgeous sunset views
Lakefront Home w/ Game Room, Theater & Dock!
Terrace/patio

Lakefront Home w/ Game Room, Theater & Dock!

3.0 star property
Lakefront Home w/ Game Room, Theater & Dock!
Twin Lakes Home - Walk to Lake Elizabeth!
Miscellaneous

Twin Lakes Home - Walk to Lake Elizabeth!

3.0 star property
Twin Lakes Home - Walk to Lake Elizabeth!
Salem Vacation Home w/ Dock: Steps to Paddock Lake
House (4 Bedrooms) | Interior

Salem Vacation Home w/ Dock: Steps to Paddock Lake

3.0 star property
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Cozy Home w/ Fire Pit: 2 Blocks to Lake Mary!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, paper towels

Cozy Home w/ Fire Pit: 2 Blocks to Lake Mary!

3.0 star property
Cozy Home w/ Fire Pit: 2 Blocks to Lake Mary!
Home on Fox River: Modern Decor Style!
Terrace/patio

Home on Fox River: Modern Decor Style!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This property is amazing! The location was perfect for our team to be able to get away to a nice and quiet place after a long day of work. The owners were very accommodating and communication was great. Thanks for a great stay! <3 The Mom Water Team "
Home on Fox River: Modern Decor Style!
Wisconsin Vacation Rental Retreat w/ Deck
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, blender

Wisconsin Vacation Rental Retreat w/ Deck

3.0 star property
Wisconsin Vacation Rental Retreat w/ Deck
Twin Lakes Escape w/ Deck < 1 Mi to Beach!
Outdoor dining

Twin Lakes Escape w/ Deck < 1 Mi to Beach!

3.0 star property
Twin Lakes Escape w/ Deck < 1 Mi to Beach!
Romantic Lake Cottage for Two. With Patio and Firepit.
Beach

Romantic Lake Cottage for Two. With Patio and Firepit.

10.0 out of 10, Exceptional, (2)
"Perfect location to relax and visit with family in the area."
Romantic Lake Cottage for Two. With Patio and Firepit.
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
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.
Don't see what you're looking for?
See all available properties in Pleasant Prairie
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (15)
"Great home and beautiful location. Thank you!"
Modern Lakeside Villa
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

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

10.0 out of 10, Exceptional, (65)
"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

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

10.0 out of 10, Exceptional, (233)
"This property is a TRUE GEM! The views and open-spaced layouts are amazing. The amenities are countless and plentiful; all that you'd want. No matter the season, this is a must stay. Everything was beautiful, clean, organized, well communicated, and just plain easy. A exemplary. Awesome Host. I will definitely be returning every year! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
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.

Frequently asked questions

Why book your cottage in Pleasant Prairie with Expedia?
Booking a cottage in Pleasant Prairie is as easy as clicking on your travel dates and picking an ideal place for outdoor relaxation and recreation. From high-end retreats to low-cost properties and cottages that include perks like a pool, Expedia has something for all tastes and styles. As for terrific deals? We’ve got them as well!
How can I find cheap cottages in Pleasant Prairie?
With Expedia’s helpful filter tool, sourcing cheap cottages in Pleasant Prairie couldn’t be simpler. To discover properties that’ll make your wallet smile, refine your search by amenities, star rating and budget.