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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windsor vacation rentals

Dining

1. Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp
Windsor
The price is AED 367
AED 666 total
includes taxes & fees
20 Aug - 21 Aug
Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp
Exterior detail

2. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (51 reviews)
"Place wa exactly as described and the owner was a great communicator. Highly recommend this place and when we return will see if it’s available ! "
United States
Angela C.
The price is AED 404
AED 670 total
includes taxes & fees
19 Aug - 20 Aug
Brickway Retreat
Exterior

3. Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (70 reviews)
"It was excellent!"
United States
Samuel D S.
The price is AED 661
AED 1,179 total
includes taxes & fees
1 Sep - 2 Sep
Fish, boat, grill, chill, pets, relax
TV

4. Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Neoga
The price is AED 496
AED 997 total
includes taxes & fees
17 Aug - 18 Aug
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Smart TV, fireplace

5. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is AED 576
AED 980 total
includes taxes & fees
2 Sep - 3 Sep
Prairieview Cabin - with Hot Tub
Exterior detail

6. Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
8.6 out of 10, Excellent, (16 reviews)
"It was very nice. I've stayed in both their 1st floor apartments now and have felt comfortable. "
United States
Rosanne D.
The price is AED 389
AED 564 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Microwave, oven, stovetop, dishwasher

7. Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Sullivan
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. It was close proximity to the beach on Lake Shelbyville and the property was clean."
United States
aubrey m.
The price is AED 760
AED 1,144 total
includes taxes & fees
13 Sep - 14 Sep
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Exterior

8. Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (18 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
The price is AED 909
AED 1,696 total
includes taxes & fees
16 Aug - 17 Aug
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Interior

9. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (61 reviews)
"Very clean and cute place! We enjoyed our stay very much. The hosts were wonderful, and we even got the blessing of a visit by the 2 puppies that live on the property. Definitely recommend staying here! "
United States
Lisa S.
The price is AED 770
AED 1,416 total
includes taxes & fees
17 Aug - 18 Aug
Prairieview Cottage Retreat - Hot Tub Sunsets
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 Windsor Hotel Reviews

Fairfield by Marriott Inn & Suites Mattoon

Fairfield by Marriott Inn & Suites Mattoon

10/10 Excellent
"To the point. Stay here save your self looking for something else. Long answer: Brand new hotel. And it feels like it. Place is very clean. Staff are very nice and helpful. Breakfast was good. Through the coffee was weak. (Can’t win it all I suppose.) I did have an extra guest in my shower, but the little fellow was easily relocated. It’s a hotel it’s never going to be perfect. But I would absolutely plan any travels on the area so I could stay here at the end of the day."
A 1-night trip
Posted 8 hours ago
Fairfield by Marriott Inn & Suites Mattoon

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we have vacation rentals close to the most popular sights in Windsor, or you can choose a more remote option if you're looking for relaxation. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Paradise Found in Illinois: This vacation home rental near Windsor is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Windsor?

While you're exploring the area, Lake Shelbyville and Lake Shelbyville Beach are a couple of picturesque spots to get outside and enjoy nature. Wolf Creek State Park and Eagle Creek State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.