Windsor Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windsor Vacation Homes

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
Wooded rural country estate near Lake Shelbyville and Illinois Amish country
Fully equipped kitchen with a stove, sink, and ample countertop space.

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
Enjoy cooking in this well-equipped kitchen with a central island, light cabinetry, and a black countertop.

Paradise Found in Illinois

10.0 out of 10, Exceptional, (169)
"We always look forward to staying at this location. Very cozy and comfortable!"
Paradise Found in Illinois
Eagle's Nest near Eagle Creek State Park
Compact kitchen with white cabinetry, stainless steel appliances, and a black gas range.

Eagle's Nest near Eagle Creek State Park

9.6 out of 10, Exceptional, (12)
"It was very nice. Clean and affordable. We would stay there again."
Eagle's Nest near Eagle Creek State Park
Brickway Retreat
Enjoy cooking in this well-lit kitchen with a central island and appliances.

Brickway Retreat

9.8 out of 10, Exceptional, (35)
"Great place to stay very clean! Many choices close by for meals."
The price is CA $151
CA $249 total
includes taxes & fees
Aug 14 - Aug 15
Brickway Retreat
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and spacious island with sink and countertop space.

Woodsy Home w/ View, 1 Mi to Lake Shelbyville

9.0 out of 10, Wonderful, (34)
"This is our 2nd year staying at the property. The house is clean & had plenty of space for our family. It’s in a quiet neighborhood & backs up to nature."
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Newly Remodeled! Mattoon Room: B4 - Queen
Relax in a spacious, open-plan area with a fireplace and ambient lighting.

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 CA $85
CA $124 total
includes taxes & fees
Aug 10 - Aug 11
Newly Remodeled! Mattoon Room: B4 - Queen
Lake Mattoon Lakehouse
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, stove, and sink.

Lake Mattoon Lakehouse

9.4 out of 10, Exceptional, (13)
"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!!
Enjoy ping pong games in this spacious indoor area with high ceilings and metal-lined walls.

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

10.0 out of 10, Exceptional, (19)
"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
Escape to a serene cabin retreat surrounded by lush trees and a natural rock formation.

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 CA $348
CA $600 total
includes taxes & fees
Aug 18 - Aug 19
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Fish, boat, grill, chill, pets, relax
Enjoy meals in the kitchen with a central island, dishwasher, and sink, adjacent to a dining area with a table and chairs.

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
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)
"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
Enter a charming two-story building with a front door and small porch area, set amidst a well-maintained lawn and trees.

Secluded cottage, sleeps 4, private and peaceful

Secluded cottage, sleeps 4, private and peaceful
Newly Remodeled! B2 - Two Room Suite, King & Queen
Cozy retreat with a central fireplace, light wood flooring, and a potted plant.

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

8.8 out of 10, Excellent, (3)
"Property was clean and quiet. Was very nice for the money."
The price is CA $114
CA $156 total
includes taxes & fees
Aug 8 - Aug 9
Newly Remodeled! B2 - Two Room Suite, King & Queen
Newly updated and cozy home! Located near downtown!
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and classic wooden cabinets.

Newly updated and cozy home! Located near downtown!

8.8 out of 10, Excellent, (11)
"Great!"
Newly updated and cozy home! Located near downtown!
Updated spacious 2 br Flat
Stylish hallway with a blue armchair, wooden cabinet, and potted plant.

Updated spacious 2 br Flat

9.0 out of 10, Wonderful, (2)
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
Updated spacious 2 br Flat
Newly Remodeled! B5 - Two Room Suite, King & Queen
Cozy retreat with a fireplace, natural light, and a large potted plant.

Newly Remodeled! B5 - Two Room Suite, King & Queen

8.0 out of 10, Very good, (1)
"The rooms were clean as described and very plain as pictured. The only thing s missing is a desk and chair and a place to hang clothes. "
The price is CA $131
CA $174 total
includes taxes & fees
Aug 10 - Aug 11
Newly Remodeled! B5 - Two Room Suite, King & Queen
Newly Remodeled! - B6 - Large King ADA Accessible
Experience the warmth of a central fireplace in this inviting space, featuring a light-colored floor and modern pendant lighting.

Newly Remodeled! - B6 - Large King ADA Accessible

The price is CA $149
CA $194 total
includes taxes & fees
Aug 12 - Aug 13
Newly Remodeled! - B6 - Large King ADA Accessible
Newly Remodeled! - A4 Queen Rm Private Bathroom, Shared Shower (Lockable)
Interior

Newly Remodeled! - A4 Queen Rm Private Bathroom, Shared Shower (Lockable)

The price is CA $84
CA $113 total
includes taxes & fees
Aug 10 - Aug 11
Newly Remodeled! - A4 Queen Rm Private Bathroom, Shared Shower (Lockable)
Newly Remodelled! A6 - Deluxe King Room
Property grounds

Newly Remodelled! A6 - Deluxe King Room

The price is CA $110
CA $139 total
includes taxes & fees
Aug 10 - Aug 11
Newly Remodelled! A6 - Deluxe King 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park

10/10 Excellent
"You should put in a fire pit! We brought ours and was fine with it, but it would just be more convenient to have one. "
Lori M. 3-night trip
Posted 2 days ago
Eagle's Nest near Eagle Creek State Park