Windsor Holiday Rentals from AU$113: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Windsor has to offer?

Paradise Found in Illinois : This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Holiday Rentals in Windsor

"Property was beautiful and their dog was super friendly. Will definitely be staying here again!"

includes taxes & fees

15 July - 16 July

"We always look forward to staying at this location. Very cozy and comfortable!"

"great location, quite and peace full host is awesome"

"It was very nice. Clean and affordable. We would stay there again."

"Clean, nice house, two separate apartments in the home… good food nearby! "

"We loved everything about this place!"

"House was great! We really enjoyed everything about the place! Very peaceful, clean and all around great place to stay!"

"This is definitely a repeat location for a girls’ getaway weekend. Quiet, clean, and equipped with all of the amenities. "

includes taxes & fees

16 July - 17 July

"Everything was clean and comfortable, with nice space"

includes taxes & fees

16 July - 17 July

"The house was beautiful. Amazing location with beautiful views. Comfortable beds. Everything we needed for our family."

"We have used this place a couple times. Always clean and comfortable."

"The location was perfect as it was only 11 minutes to Eastern IL Univ. The directions sent to enter the property was clear and easy to understand. Room clean and free of odor. Several chain and local restaurants nearby. "

includes taxes & fees

15 July - 16 July

"Great stay! "

"Great place to stay very clean! Many choices close by for meals."

includes taxes & fees

15 July - 16 July

"Great place to stay. Kids had a fun time with the indoor games and the location is very close to the boat ramps on the lake. Would definitely come back."

"We were pleasantly surprised with our stay in Shelbyville. The property is very nice and newly renovated. The manager was very responsive to all our needs. We would not hesitate to stay here again."

includes taxes & fees

15 July - 16 July

"Very nice property. Only suggestions would be to put a chair in each room."

includes taxes & fees

20 July - 21 July

Fridge, microwave, coffee/tea maker, toaster

"First time on this side. Wonderful stay. Close to everything. The bed is so comfy. "

includes taxes & fees

17 July - 18 July

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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$113 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.

Recent reviews of Windsor properties

5/5 Excellent

"Great place overall"

A verified traveller stayed at Comfort Suites Mattoon

Posted 3 days ago

5/5 Excellent

Ggood Time

"My wife and I went to the Lake for swimming and fishing. Although the room was not brand new it had everything we wanted. A big Jacuaai Tub / Large fridge / nice shower/ big TV and a comfortable bed. The fishing aand swimming were a walk away. The manager Rene was very helpful/ We will stay there again."

A verified traveller stayed at Spillway Motel

Posted 6 days ago

5/5 Excellent

Paradise Lake Cottage

"This cottage is the kind of place that makes you want to stay and go nowhere and just enjoy the views, morning coffee in the the glassed in and air conditioned porch, or relaxing in a chair on the dock watching the turtles and fish. Same can be said for enjoying a beverage in the evening while grilling out.Going for walks and having fun riding the paddle boat also recommended. Loved it and will definitely be staying again in the future."

A verified traveller stayed at Paradise Found in Illinois

Posted 12 days ago

Cozy Country Cabin - Sleeps 4 - with Hot Tub

5/5 Excellent

Bachelorette trip

"We had a small little bachelorette weekend to celebrate our best friend’s wedding in September. It was just three of us and this cabin was so perfect!! The host, area, property, and views were so lovely. We loved the hot tub and the friendly host dog Chase!! We can’t wait to come back again!!"

A verified traveller stayed at Cozy Country Cabin - Sleeps 4 - with Hot Tub

Posted 2 weeks ago

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?

Paradise Found in Illinois: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 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 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.

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Windsor Holiday Rentals

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Holiday Rentals in Windsor

Cozy Country Cabin - Sleeps 6 - with Hot Tub

Cozy Country Cabin - Sleeps 6 - with Hot Tub

Paradise Found in Illinois

Paradise Found in Illinois

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

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

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

Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park

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

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

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

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

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

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Lake Mattoon Lakehouse

Lake Mattoon Lakehouse

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax

Newly Remodeled! Mattoon Room: B4 - Queen

Newly Remodeled! Mattoon Room: B4 - Queen

Secluded cottage, sleeps 4, private and peaceful

Secluded cottage, sleeps 4, private and peaceful

Come Escape to Paradise on the Lake

Come Escape to Paradise on the Lake

Brickway Retreat

Brickway Retreat

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

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

Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville

Newly Remodeled! B2 - Two Room Suite, King & Queen

Newly Remodeled! B2 - Two Room Suite, King & Queen

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Find out more about Windsor

Find out more about Windsor

Recent reviews of Windsor properties

Recent reviews of Windsor properties

Comfort Suites Mattoon

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Explore a world of travel with Expedia

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