Windsor Holiday Rentals

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Holiday Rentals in Windsor

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (16)
"Property was beautiful and their dog was super friendly. Will definitely be staying here again!"
The price is AU$379
includes taxes & fees
23 July - 24 July
Cozy Country Cabin - Sleeps 6 - with Hot Tub

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

Paradise Found in Illinois

10.0 out of 10, Exceptional, (166)
"We always look forward to staying at this location. Very cozy and comfortable!"
Paradise Found in Illinois

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

9.6 out of 10, Exceptional, (10)
"It was very nice. Clean and affordable. We would stay there again."
Eagle's Nest near Eagle Creek State Park

Binion Lodge: Wooded Privacy Near Lake Shelbyville

10.0 out of 10, Exceptional, (11)
"Everything was clean and comfortable, with nice space"
The price is AU$645
includes taxes & fees
4 Aug - 5 Aug
Binion Lodge: Wooded Privacy Near Lake Shelbyville

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

9.8 out of 10, Exceptional, (19)
"House was great! We really enjoyed everything about the place! Very peaceful, clean and all around great place to stay!"
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (24)
"We loved everything about this place!"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

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.

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

10.0 out of 10, Exceptional, (32)
"This is definitely a repeat location for a girls’ getaway weekend. Quiet, clean, and equipped with all of the amenities. "
The price is AU$465
includes taxes & fees
23 July - 24 July
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Lake Mattoon Lakehouse

9.4 out of 10, Exceptional, (12)
"The house was beautiful. Amazing location with beautiful views. Comfortable beds. Everything we needed for our family."
Lake Mattoon Lakehouse

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

10.0 out of 10, Exceptional, (17)
"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!!

Fish, boat, grill, chill, pets, relax

9.6 out of 10, Exceptional, (57)
"We have used this place a couple times. Always clean and comfortable."
Fish, boat, grill, chill, pets, relax

Come Escape to Paradise on the Lake

2.0 star property
10.0 out of 10, Exceptional, (11)
"Would prefer curtains on the French doors. Loved the sun room. Streaming Tv not so much. Comfortable, quiet. Haven't been near a lake in midsummer that was so quiet !"
Come Escape to Paradise on the Lake

Secluded cottage, sleeps 4, private and peaceful

Secluded cottage, sleeps 4, private and peaceful

Newly Remodeled! Mattoon Room: B4 - Queen

10.0 out of 10, Exceptional, (1)
"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. "
The price is AU$121
includes taxes & fees
23 July - 24 July
Newly Remodeled! Mattoon Room: B4 - Queen

Brickway Retreat

9.8 out of 10, Exceptional, (34)
"Great place to stay very clean! Many choices close by for meals."
The price is AU$247
includes taxes & fees
27 July - 28 July
Brickway Retreat

Cozy, and private apartment near Lake Shelbyville

9.8 out of 10, Exceptional, (13)
"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 AU$227
includes taxes & fees
31 July - 1 Aug
Cozy, and private apartment near Lake Shelbyville

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

9.0 out of 10, Wonderful, (2)
"Very nice property. Only suggestions would be to put a chair in each room."
The price is AU$131
includes taxes & fees
24 July - 25 July
Newly Remodeled! B2 - Two Room Suite, King & Queen

Newly updated and cozy home! Located near downtown!

8.8 out of 10, Excellent, (10)
"Great!"
Newly updated and cozy home! Located near downtown!
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

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. 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.