Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (46 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$254
includes taxes & fees
29 Apr - 30 Apr
Brickway Retreat

Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (35 reviews)
"Great getaway! 2 adults relaxing and enjoyed the tranquility. Spacious and really enjoyed the porch and hot tub. "
United States
Ana Rosa R.
The price is AU$363
includes taxes & fees
3 May - 4 May
Prairieview Cabin - with Hot Tub

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.6 out of 10, Exceptional, (63 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$400
includes taxes & fees
22 Apr - 23 Apr
Fish, boat, grill, chill, pets, relax

Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park
Findlay
9.4 out of 10, Exceptional, (17 reviews)
"Amazing host and property. "
United States
Nicholas K.
The price is AU$352
includes taxes & fees
23 Apr - 24 Apr
Eagle's Nest near Eagle Creek State Park

Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville
Shelbyville
9.8 out of 10, Exceptional, (22 reviews)
"Excellent stay. Very nice accommodations. Will absolutely be staying there again the next time we are in town. "
United States
Brandon S.
The price is AU$209
includes taxes & fees
27 Apr - 28 Apr
Cozy, and private apartment near Lake Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
8.8 out of 10, Excellent, (10 reviews)
"Place was very clean, convenient location, and I will definitely use again. "
United States
Jim B.
The price is AU$217
includes taxes & fees
26 Apr - 27 Apr
Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (54 reviews)
"It was a wonderful stay. We loved the location and the patio during the evening!"
United States
Lyndsey C.
The price is AU$482
includes taxes & fees
28 Apr - 29 Apr
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$239
includes taxes & fees
28 Apr - 29 Apr
Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (14 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
The price is AU$611
includes taxes & fees
27 Apr - 28 Apr
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Country Comfort House • Relax, Recharge, Repeat

Country Comfort House • Relax, Recharge, Repeat
Sullivan
The price is AU$417
includes taxes & fees
23 Apr - 24 Apr
Country Comfort House • Relax, Recharge, Repeat

The Emerald Escape: Moody emerald loft near the lake.

The Emerald Escape: Moody emerald loft near the lake.
Shelbyville
6.0 out of 10, (2 reviews)
"Property was very clean, the indoor spaces are even nicer than in the pictures, great location, owner responded very quick to inquires "
United States
Karen L.
The price is AU$209
includes taxes & fees
2 May - 3 May
The Emerald Escape: Moody emerald loft near the lake.
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$209 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?

Prairieview Cabin - with Hot Tub: This holiday home rental outside of Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 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. Mattoon City Hall 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.