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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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
$172 nightly
The price is $182
Aug 13 - Aug 14
Total with taxes and fees
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.
$170 nightly
The price is $180
Aug 10 - Aug 11
Total with taxes and fees
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)
"We had a great night here. We stayed after attending our grandson's 1st birthday party in Decatur. We and our other family from Chicago spent the night. Everything was very clean. The kitchen is fully stocked with plates, cups, utensils, bowls and even cooking tools should you need them. We loved the plastic children's cups and plates as well. I really appreciated the coffee, creamer and sugar provided!If you have your pet with you, there is a side by side food and water dish in the dining area...
United States
Brian P.
$300 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
Fish, boat, grill, chill, pets, relax
Smart TV, fireplace

4. 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.
$261 nightly
The price is $263
Sep 2 - Sep 3
Total with taxes and fees
Prairieview Cabin - with Hot Tub
Exterior detail

5. 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.
$125 nightly
The price is $132
Aug 7 - Aug 8
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Microwave, oven, stovetop, dishwasher

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.
$263 nightly
The price is $279
Aug 16 - Aug 17
Total with taxes and fees
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
TV

7. 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
$256 nightly
The price is $271
Aug 17 - Aug 18
Total with taxes and fees
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
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.
$444 nightly
The price is $462
Aug 9 - Aug 10
Total with taxes and fees
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.
$377 nightly
The price is $380
Aug 11 - Aug 12
Total with taxes and fees
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

Comfort Suites Mattoon East

Comfort Suites Mattoon East

10/10 Excellent
"Nothing bad to say, it was clean and the staff was very accommodating."
Glenn 1-night trip
Posted 17 hours ago
Comfort Suites Mattoon East

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $132 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Fish, boat, grill, chill, pets, relax: This vacation home rental near Windsor is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the arcade game room in this rental home to help you unwind.

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 Forest 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.