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Top Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (17)
"Great place! "
The price is £203
includes taxes & fees
28 Aug - 29 Aug
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

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 £267
includes taxes & fees
28 Aug - 29 Aug
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Eagle's Nest near Eagle Creek State Park

9.4 out of 10, Exceptional, (13)
"Amazing host and property. "
The price is £186
includes taxes & fees
22 Sept - 23 Sept
Eagle's Nest near Eagle Creek State Park

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 £113
includes taxes & fees
31 Aug - 1 Sept
Cozy, and private apartment near Lake Shelbyville

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

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

9.4 out of 10, Exceptional, (3)
"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.

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.

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

10.0 out of 10, Exceptional, (20)
"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!!

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

9.8 out of 10, Exceptional, (36)
"Great place to stay very clean! Many choices close by for meals."
The price is £136
includes taxes & fees
31 Aug - 1 Sept
Brickway Retreat

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

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

Binion Lodge: Wooded Privacy Near Lake Shelbyville

10.0 out of 10, Exceptional, (13)
"Everything was clean and comfortable, with nice space"
The price is £330
includes taxes & fees
9 Sept - 10 Sept
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Come Escape to Paradise on the Lake

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great stay! "
Come Escape to Paradise on the Lake

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 £195
includes taxes & fees
20 Sept - 21 Sept
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

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

9.6 out of 10, Exceptional, (58)
"Perfect place and location to State Parks and Boat launches. Very comfortable and fully equipped. We will be back!"
Fish, boat, grill, chill, pets, relax

Newly updated and cozy home! Located near downtown!

9.0 out of 10, Wonderful, (12)
"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!

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway

The Little House on Prairie: Family-Friendly 2-Bedroom Getaway
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?

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.