Holiday Rentals in Windsor

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Holiday Rentals in Windsor

Cozy, and private apartment near Lake Shelbyville
Interior

Cozy, and private apartment near Lake Shelbyville

9.6 out of 10, Exceptional, (14)
"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."
The price is €131
includes taxes & fees
30 Sept - 1 Oct
Cozy, and private apartment near Lake Shelbyville
Cozy Country Cabin - Sleeps 6 - with Hot Tub
Exterior

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (17)
"Great place! "
The price is €222
includes taxes & fees
2 Sept - 3 Sept
Cozy Country Cabin - Sleeps 6 - with Hot Tub
Wooded rural country estate near Lake Shelbyville and Illinois Amish country
Fridge, microwave, oven, stovetop

Wooded rural country estate near Lake Shelbyville and Illinois Amish country

10.0 out of 10, Exceptional, (40)
"great location, quite and peace full host is awesome"
Wooded rural country estate near Lake Shelbyville and Illinois Amish country
Eagle's Nest near Eagle Creek State Park
Fridge, microwave, oven, stovetop

Eagle's Nest near Eagle Creek State Park

9.4 out of 10, Exceptional, (13)
"Amazing host and property. "
The price is €216
includes taxes & fees
22 Sept - 23 Sept
Eagle's Nest near Eagle Creek State Park
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Fridge, microwave, coffee/tea maker, toaster

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

8.0 out of 10, Very good, (4)
"First time on this side. Wonderful stay. Close to everything. The bed is so comfy. "
The price is €114
includes taxes & fees
2 Sept - 3 Sept
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Exterior

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (25)
"We loved everything about this place!"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
Interior

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

9.4 out of 10, Exceptional, (44)
"Clean, nice house, two separate apartments in the home… good food nearby! "
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
A Novel Stay 3bd log cabin with Hot tub in amazing Shelbyville, IL. 3.5 acres.
Exterior

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

10.0 out of 10, Exceptional, (2)
"Such a cute cabin. So many well thought out and helpful amenities. Comfortable bedroom spaces and beds. Best part is that its not far from our favorite place, lake Shelbyville!"
A Novel Stay 3bd log cabin with Hot tub in amazing Shelbyville, IL. 3.5 acres.
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Outdoor dining

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

10.0 out of 10, Exceptional, (36)
"This is definitely a repeat location for a girls’ getaway weekend. Quiet, clean, and equipped with all of the amenities. "
The price is €294
includes taxes & fees
2 Sept - 3 Sept
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
Outdoor dining

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

9.8 out of 10, Exceptional, (24)
"We really enjoy our stay here and hope to continue to stay here every year we make our trip to Shelbyville! Great place!"
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
Newly updated and cozy home! Located near downtown!
Interior

Newly updated and cozy home! Located near downtown!

9.0 out of 10, Wonderful, (14)
"This home has everything anyone would need. Be it a single person or a family. Our host is awesome also. "
Newly updated and cozy home! Located near downtown!
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Property grounds

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

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay! The place is so clean and cute and cozy! We definitely felt right at home! Can’t wait to stay again soon! Thank you! "
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Brickway Retreat
Fridge, microwave, oven, stovetop

Brickway Retreat

9.8 out of 10, Exceptional, (36)
"Great place to stay very clean! Many choices close by for meals."
The price is €158
includes taxes & fees
2 Sept - 3 Sept
Brickway Retreat
Paradise Found in Illinois
Fridge, microwave, oven, stovetop

Paradise Found in Illinois

10.0 out of 10, Exceptional, (171)
"We always look forward to staying at this location. Very cozy and comfortable!"
Paradise Found in Illinois
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Games room

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

10.0 out of 10, Exceptional, (22)
"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."
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Exterior

Binion Lodge: Wooded Privacy Near Lake Shelbyville

10.0 out of 10, Exceptional, (14)
"Everything was clean and comfortable, with nice space"
The price is €386
includes taxes & fees
2 Sept - 3 Sept
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Come Escape to Paradise on the Lake
Property grounds

Come Escape to Paradise on the Lake

2.0 star property
10.0 out of 10, Exceptional, (11)
"Enjoyed the house very much! It is a sweet little house, but has everything you might need. "
Come Escape to Paradise on the Lake
Lake Mattoon Lakehouse
Microwave, oven, stovetop, dishwasher

Lake Mattoon Lakehouse

9.4 out of 10, Exceptional, (13)
"We gathered together for a graduation weekend and had a relaxing time in a roomy house right next to the lake cove. Very pleased "
Lake Mattoon Lakehouse
Fish, boat, grill, chill, pets, relax
Fridge, microwave, oven, stovetop

Fish, boat, grill, chill, pets, relax

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. "
Fish, boat, grill, chill, pets, relax
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Fridge, microwave, oven, stovetop

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

10.0 out of 10, Exceptional, (1)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
The price is €226
includes taxes & fees
20 Sept - 21 Sept
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
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

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, apart-hotels, 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 favorite 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 depends 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 €131 per night. Entering your travel dates in the search wizard you might find 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?

Eagle's Nest near Eagle Creek State Park: This holiday home rental outside of Windsor is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.