Windsor Holiday Rentals

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Our top choices for Windsor holiday 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.
The price is AU$287
includes taxes & fees
29 June - 30 June
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
The price is AU$255
includes taxes & fees
8 June - 9 June
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.
The price is AU$660
includes taxes & fees
22 June - 23 June
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.
The price is AU$380
includes taxes & fees
23 June - 24 June
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.
The price is AU$519
includes taxes & fees
17 June - 18 June
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
The price is AU$524
includes taxes & fees
29 June - 30 June
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
The price is AU$258
includes taxes & fees
18 June - 19 June
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.
The price is AU$186
includes taxes & fees
7 June - 8 June
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
The price is AU$383
includes taxes & fees
8 June - 9 June
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
The price is AU$389
includes taxes & fees
15 June - 16 June
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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?

Fish, boat, grill, chill, pets, relax: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of an arcade/games 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 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.