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
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 41 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!
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
Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports
Property grounds

Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports

9.6 out of 10, Exceptional, (19)
"Had everything we needed"
Lakefront, Newly Renovated, Tranquil Getaway, Free Water Sports
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
Updated Twin Lakes Cottage, Walk to Lake Mary
Interior

Updated Twin Lakes Cottage, Walk to Lake Mary

9.8 out of 10, Exceptional, (36)
"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
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!
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
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
Amazing summer lake escape in our waterfront cottage!!!
Exterior

Amazing summer lake escape in our waterfront cottage!!!

9.4 out of 10, Exceptional, (35)
"This is the 2nd time we rented this property and both times we had a great time . Kind of a quirky place with a mix of old and new. The grandkids loved a lot of the 50+ year old games. Hosts were easy to contact and replied quickly to any questions or concerns."
Amazing summer lake escape in our waterfront cottage!!!
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
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!
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!
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

3.0 star property
Riverfront Libertyville Retreat w/ Outdoor Kitchen
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!
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
House (2 Bedrooms) | Interior

Lakefront Antioch Home w/ Dock, Kayaks & Game Room

3.0 star property
Lakefront Antioch Home w/ Dock, Kayaks & Game Room
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!
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!
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
Lakefront cottage with gorgeous sunset views
Property grounds

Lakefront cottage with gorgeous sunset views

Lakefront cottage with gorgeous sunset views
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

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.
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (199)
"What a fun and unique place! I'd love to be back in summer to make use of the pool and pond.Winter was still wonderful though with access to the hot tub and game room. "
The price is AED 551
AED 1,762 total
includes taxes & fees
17 Mar - 18 Mar
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
3-bedroom vacation home just a short walk to Lake Michigan
Terrace/patio

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

9.6 out of 10, Exceptional, (14)
"I got a great deal on a 2 bedroom and I'm looking forward to coming back during the summer since it is a great location next to lake and beach. "
The price is AED 342
AED 793 total
includes taxes & fees
16 Mar - 17 Mar
3-bedroom vacation home just a short walk to Lake Michigan
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?
Expedia has some wonderful cottages in Pleasant Prairie, so get ready for a memorable vacation on nature’s doorstep. If you’re on a budget, select how much you’re willing to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a hot tub or free WiFi. We’ll help you find a suitable place whatever your style of travel or plans.
How can I find cheap cottages in Pleasant Prairie?
The best way to spot cheap cottages in Pleasant Prairie is with Expedia’s convenient filter tool. Narrow your search results by amenities, budget and star rating to access unbeatable bargains in just a few clicks.