Title: Windsor, IL Cottage Rentals from $332 | Expedia.com

[Windsor Travel Guide](https://expedia.com/Windsor.dx175567)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d175567.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d175567.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d175567.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d175567.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d175567.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=175567&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=175567&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=175567&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=175567&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor cottages

![Exterior](https://images.trvl-media.com/lodging/85000000/84100000/84093500/84093479/315e3228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/85000000/84100000/84093500/84093479/01ed9b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84100000/84093500/84093479/88f5e263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/85000000/84100000/84093500/84093479/02937673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

[](https://www.expedia.com/Sullivan-Hotels-Prairieview-Cottage-Retreat-Home-Away-From-Home.h84093479.Hotel-Information)

Sullivan

10/10

Exceptional

(51 reviews)

"It was a wonderful stay. We loved the location and the patio during the evening!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lyndsey C.

$314 nightly

$332 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Sullivan-Hotels-Prairieview-Cottage-Retreat-Home-Away-From-Home.h84093479.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19&regionId=175567&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Illinois%2C+United+States+of+America&regionId=175567&latLong=39.440869%2C-88.59478&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Illinois%2C+United+States+of+America&regionId=175567&latLong=39.440869%2C-88.59478&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Illinois%2C+United+States+of+America&regionId=175567&latLong=39.440869%2C-88.59478&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Illinois%2C+United+States+of+America&regionId=175567&latLong=39.440869%2C-88.59478&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE)

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## Top Windsor Hotel Reviews

![Suite Dreams Motel By Capital O Mattoon I - 57](https://images.trvl-media.com/lodging/16000000/15350000/15340400/15340340/31e5b1e4_y.jpg)

### Suite Dreams Motel By Capital O Mattoon I - 57

10/10 Excellent

"Enjoyed our time friendly people and clean"

[](https://expedia.com/Effingham-Hotels-Suite-Dreams-Hotel.h15340340.Hotel-Information)

![Hilton Garden Inn Mattoon,  Il](https://images.trvl-media.com/lodging/79000000/78290000/78285200/78285150/12c48720_y.jpg)

### Hilton Garden Inn Mattoon, Il

10/10 Excellent

"Staff, cleanliness, comfort"

[](https://expedia.com/Mattoon-Hotels-Hilton-Garden-Inn-Mattoon.h78285150.Hotel-Information)

![Comfort Suites Mattoon East](https://images.trvl-media.com/lodging/1000000/480000/474300/474235/6759fc3e_y.jpg)

### Comfort Suites Mattoon East

10/10 Excellent

"Clean hotel in every area visited, staff friendly and helpful, everything you needed for a comfortable stay, pool and gym better than expected, and breakfast was great! Thank you!"

[](https://expedia.com/Effingham-Hotels-Comfort-Suites-Mattoon.h474235.Hotel-Information)

![Spacious 5-bedroom Home Centrally Located-Sleeps 14!](https://images.trvl-media.com/lodging/122000000/121220000/121217100/121217007/f8091d21_y.jpg)

### Spacious 5-bedroom Home Centrally Located-Sleeps 14!

10/10 Excellent

"This is a clean and neatly appointed home perfect for a family get together or a vacation! The beds are comfortable and it is conveniently located to the lake and morning walks over the dam and downtown for coffee or light shopping. Great small touches that make it easy to stay! We will be back! "

[](https://expedia.com/Shelbyville-Hotels-Spacious-5-Bedroom-Home-Centrally-Located-Sleeps-14.h121217007.Hotel-Information)

![Cozy Country Cabin - Sleeps 6 - with Hot Tub](https://images.trvl-media.com/lodging/107000000/106930000/106921000/106920960/b40c7188_y.jpg)

### Cozy Country Cabin - Sleeps 6 - with Hot Tub

10/10 Excellent

"Very Comfy !"

[](https://expedia.com/Sullivan-Hotels-Cozy-Country-Cabin-Sleeps-4-With-Hot-Tub.h106920960.Hotel-Information)

![Clarion Pointe Mattoon near University](https://images.trvl-media.com/lodging/1000000/20000/10800/10742/6dee7d6c_y.jpg)

### Clarion Pointe Mattoon near University

10/10 Excellent

"Staff was excellent and always did everything I needed at a moments notice "

[](https://expedia.com/Mattoon-Hotels-Baymont-By-Wyndham-Mattoon.h10742.Hotel-Information)

![The Shelby Inn](https://images.trvl-media.com/lodging/2000000/1510000/1502100/1502050/257400e9_y.jpg)

### The Shelby Inn

10/10 Excellent

"Clean comfortable and friendly"

[](https://expedia.com/Effingham-Hotels-The-Shelby-Inn.h1502050.Hotel-Information)

![Super 8 by Wyndham Mattoon](https://images.trvl-media.com/lodging/1000000/50000/49800/49707/2e073a1e_y.jpg)

### Super 8 by Wyndham Mattoon

10/10 Excellent

"The staff went above and beyond to accommodate me and my family "

[](https://expedia.com/Effingham-Hotels-Super-8-By-Wyndham-Mattoon.h49707.Hotel-Information)

![Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8](https://images.trvl-media.com/lodging/85000000/84100000/84093500/84093479/9cfeccb9_y.jpg)

### Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

10/10 Excellent

"Great experience. "

[](https://expedia.com/Sullivan-Hotels-Prairieview-Cottage-Retreat-Home-Away-From-Home.h84093479.Hotel-Information)

## Find out more about Windsor

## Windsor Cottages information

| Number of reviews | 51         |
| ----------------- | ---------- |
| Accommodation     | 3 Cottages |
| Lowest Price      | $332       |
| Highest Price     | $332       |

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