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Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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 NZ$301
includes taxes & fees
20 Sept - 21 Sept
Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

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

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (71 reviews)
"It was excellent!"
United States
Samuel D S.
The price is NZ$489
includes taxes & fees
1 Sept - 2 Sept
Fish, boat, grill, chill, pets, relax

3. 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 NZ$301
includes taxes & fees
25 Aug - 26 Aug
Brickway Retreat

4. 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 NZ$257
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-bedroom with AC and WiFi in charming Shelbyville

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 NZ$432
includes taxes & fees
2 Sept - 3 Sept
Prairieview Cabin - with Hot Tub

6. 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 NZ$461
includes taxes & fees
23 Aug - 24 Aug
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds

7. 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 NZ$762
includes taxes & fees
24 Aug - 25 Aug
Binion Lodge: Wooded Privacy Near Lake Shelbyville

8. 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 NZ$451
includes taxes & fees
24 Aug - 25 Aug
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

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 NZ$625
includes taxes & fees
15 Sept - 16 Sept
Prairieview Cottage Retreat - Hot Tub Sunsets

10. Family Friendly Cottage in the Countryside

Family Friendly Cottage in the Countryside
Toledo
10.0 out of 10, Exceptional, (2 reviews)
"Very nice very quiet peaceful surroundings"
United States
Tony P.
The price is NZ$596
includes taxes & fees
24 Aug - 25 Aug
Family Friendly Cottage in the Countryside
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

Find out more about Windsor

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

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

Paradise Found in Illinois: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ 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 holiday with amenities such as 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 wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.