Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
Mattoon
10.0 out of 10, Exceptional, (10 reviews)
"Had a great time with our family and it was close to arthur"
United States
Daniel S.
$189 nightly
The price is $201
Jun 29 - Jun 30
Total with taxes and fees
The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (47 reviews)
"It was a wonderful experience. The accommodations were perfect for our family of 7. It was so much better than booking multiple hotel rooms. "
United States
VINCENT
$170 nightly
The price is $180
Jun 7 - Jun 8
Total with taxes and fees
Brickway Retreat

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (16 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
$449 nightly
The price is $482
Jun 10 - Jun 11
Total with taxes and fees
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (38 reviews)
"Very nice place to stay!"
United States
Brandon R.
$262 nightly
The price is $264
Jun 15 - Jun 16
Total with taxes and fees
Prairieview Cabin - with Hot Tub

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (68 reviews)
"Our host did a great job for us. Answered any questions we asked and was very accommodating.Unit was clean, well stocked and met our needs.Thanks for a great stay Greatly appreciated "
United States
Kevin P.
$268 nightly
The price is $284
Jun 9 - Jun 10
Total with taxes and fees
Fish, boat, grill, chill, pets, relax

Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (59 reviews)
"Communication was great. Check in was super easy. Home was beautiful, and had everything you would ever need. Beautiful, quiet location."
United States
Melissa
$368 nightly
The price is $371
Jun 15 - Jun 16
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets

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
$171 nightly
The price is $181
Jun 13 - Jun 14
Total with taxes and fees
Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
9.0 out of 10, Wonderful, (11 reviews)
"Well appointed with a large bedroom and family/sitting room and a large combination kitchenette/laundry area. Plenty of parking and a useable porch area. Lots of room to spread out. "
United States
Kevin B.
$122 nightly
The price is $129
Jun 7 - Jun 8
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville

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
Jun 8 - Jun 9
Total with taxes and fees
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

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
$263 nightly
The price is $279
Jun 8 - Jun 9
Total with taxes and fees
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
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

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 $129 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 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.