Windsor Holiday Rentals

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Holiday Rentals in Windsor

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Sullivan
10.0 out of 10, Exceptional, (45)
"This property is beautiful, we had a great time relaxing at this comfortable cottage. "
United States
Michael C.
The price is AU$549
includes taxes & fees
11 Nov - 12 Nov
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
Sullivan
10.0 out of 10, Exceptional, (22)
"The cabin was clean and had all the amenities needed for an escape from society. Its far enough from town to feel secluded but close enough that you can easily drive in to grab essentials. The hot tub was clean and a preheated for our stay. The hardest part about the entire stay was leaving. It felt nice to get away for a few days. "
United States
Kelly
The price is AU$390
includes taxes & fees
10 Nov - 11 Nov
Cozy Country Cabin - Sleeps 6 - with Hot Tub

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Shelbyville
8.8 out of 10, Excellent, (6)
"On our way to the property, they messaged us to say that they had double booked the unit we had reserved and that we would have to stay in a different unit. Second and much bigger problem was that the AC did not work. When we got there we turned the thermostat down as it read 80 at our arrival. The outside temperature at the time was in the mid-90s. Two hours later it still was at 80 when we had turned it down to 70 earlier. We then messaged the host to let him know. He assured us it would cool...
United States
Mindye M.
The price is AU$202
includes taxes & fees
10 Nov - 11 Nov
Cozy 1-bedroom with AC and WiFi in charming Shelbyville

A Novel Stay 3bd log cabin with Hot tub in amazing Shelbyville, IL. 3.5 acres.

Shelbyville
9.2 out of 10, Wonderful, (5)
"Perfect Spot for a Bestie Getaway! We found this gem for our annual bestie trip, and it was perfect! The location couldn’t be better, right by Lithia Springs Marina (literally 2 min drive). Nichole was amazing from the start, super helpful and friendly. The house is beautifully decorated and thoughtfully stocked with everything you could need.We grilled on the Blackstone, soaked in the hot tub, and had a blast with outdoor Jenga and cornhole. The kids loved spotting deer every day! There was...
United States
Jennifer B.
A Novel Stay 3bd log cabin with Hot tub in amazing Shelbyville, IL. 3.5 acres.

Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!

Findlay
10.0 out of 10, Exceptional, (25)
"Great place to stay with my family! Very beautiful inside and out and plenty of room for everyone! Will definitely be back!"
United States
Nichole S.
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!

Eagle's Nest near Eagle Creek State Park

Findlay
9.2 out of 10, Wonderful, (15)
"Amazing host and property. "
United States
Nicholas K.
The price is AU$335
includes taxes & fees
10 Nov - 11 Nov
Eagle's Nest near Eagle Creek State Park

Brickway Retreat

Mattoon
9.8 out of 10, Exceptional, (38)
"This property was very clean, super cute and very comfortable. The character that was maintained in the home, while being updated was amazing! I will definitely stay here again! "
United States
Amanda J.
The price is AU$281
includes taxes & fees
19 Nov - 20 Nov
Brickway Retreat

Lake Mattoon Lakehouse

Neoga
9.4 out of 10, Exceptional, (16)
"We gathered together for a graduation weekend and had a relaxing time in a roomy house right next to the lake cove. Very pleased "
United States
Kirk V.
Lake Mattoon Lakehouse

Paradise Found in Illinois

Mattoon
10.0 out of 10, Exceptional, (172)
"We have stayed here several times. We enjoy observing the seasonal changes and the birdlife. It's a cozy retreat."
United States
Richard and Rhonda
Paradise Found in Illinois

Come Escape to Paradise on the Lake

2.0 star property
Mattoon
10.0 out of 10, Exceptional, (13)
"Enjoyed the house very much! It is a sweet little house, but has everything you might need. "
United States
pankey128@yahoo.com P.
Come Escape to Paradise on the Lake

Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake

Shelbyville
9.6 out of 10, Exceptional, (25)
"Overall great space. Plenty of room and outdoor space was top notch. "
United States
Sean W.
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake

Fish, boat, grill, chill, pets, relax

Sullivan
9.6 out of 10, Exceptional, (58)
"The condo is nice and clean, and so close to the lake. The experience has been wonderful, and Stacey is great to work with. It backs right up to the golf course, a short walk to the campgrounds, and an easy trail to the lake. "
United States
Audrey M.
The price is AU$437
includes taxes & fees
30 Nov - 1 Dec
Fish, boat, grill, chill, pets, relax

Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.

Shelbyville
9.4 out of 10, Exceptional, (45)
"Nice accommodations for what we needed."
United States
Anita W.
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

Lakewood
10.0 out of 10, Exceptional, (31)
"Beautiful property. Couldn’t be better. "
United States
Michael s.
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds

Lakewood
9.8 out of 10, Exceptional, (6)
"Check-in was smooth, very nice property. Kitchen nice and roomy as well as rest of house had all we needed for our long weekend trip. We grilled, relaxed on deck over looking ponds and fished here a lil. Not to mention fun days on lake and at beach. We will definitely be back!"
United States
Anastasia C.
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds

Newly updated and cozy home! Located near downtown!

Mattoon
9.2 out of 10, Wonderful, (15)
"It was conveniently located near the train station and restaurants. The host was always quick to respond to inquiries. "
United States
Linda M.
Newly updated and cozy home! Located near downtown!

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Sullivan Township
10.0 out of 10, Exceptional, (14)
"Peaceful, beautiful place"
United States
Maria G.
The price is AU$630
includes taxes & fees
24 Nov - 25 Nov
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville

Shelbyville
9.6 out of 10, Exceptional, (18)
"Location😁 App coordination between Expedia and Vrbo😒"
United States
Paul
The price is AU$232
includes taxes & fees
12 Nov - 13 Nov
Cozy, and private apartment near Lake Shelbyville

Woodsy Home w/ View, 1 Mi to Lake Shelbyville

3.0 star property
Shelbyville
Woodsy Home w/ View, 1 Mi to Lake Shelbyville

Bring The Whole Crew, We've Got Room!

Mattoon
Bring The Whole Crew, We've Got Room!
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$202 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?

Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!: This holiday home rental outside of Windsor offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. Eagle Creek State Park and Wolf 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.