Windsor Vacation Rentals

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

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
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
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
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)
"Family had a great time. Location couldn’t be better right next to Eagle Creek. Property was very clean no complaints."
Eagle's Nest near Eagle Creek State Park
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 CA $152
CA $249 total
includes taxes & fees
Aug 31 - Sep 1
Brickway Retreat
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Fridge, microwave, stovetop, dishwasher

Woodsy Home w/ View, 1 Mi to Lake Shelbyville

9.0 out of 10, Wonderful, (34)
"Well equipped, nice location, close to boat ramp. Four guys on fishing trip."
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Newly Remodeled! Mattoon Room: B4 - Queen
Interior

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 $80
CA $118 total
includes taxes & fees
Aug 21 - Aug 22
Newly Remodeled! Mattoon Room: B4 - Queen
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
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Game room

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!!
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Exterior

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 $350
CA $603 total
includes taxes & fees
Aug 25 - Aug 26
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Fish, boat, grill, chill, pets, relax
Fridge, microwave, oven, stovetop

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)
"Great stay! "
Come Escape to Paradise on the Lake
Secluded cottage, sleeps 4, private and peaceful
Exterior

Secluded cottage, sleeps 4, private and peaceful

Secluded cottage, sleeps 4, private and peaceful
Newly Remodeled! B2 - Two Room Suite, King & Queen
Interior

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."
Newly Remodeled! B2 - Two Room Suite, King & Queen
Newly updated and cozy home! Located near downtown!
Interior

Newly updated and cozy home! Located near downtown!

8.8 out of 10, Excellent, (11)
"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!
Updated spacious 2 br Flat
Interior

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
Interior

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 $119
CA $161 total
includes taxes & fees
Aug 21 - Aug 22
Newly Remodeled! B5 - Two Room Suite, King & Queen
Newly Remodeled! - B6 - Large King ADA Accessible
Interior

Newly Remodeled! - B6 - Large King ADA Accessible

The price is CA $154
CA $200 total
includes taxes & fees
Aug 24 - Aug 25
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 $77
CA $107 total
includes taxes & fees
Aug 21 - Aug 22
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 $102
CA $131 total
includes taxes & fees
Aug 21 - Aug 22
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.
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Top Windsor Hotel Reviews

Quality Inn & Suites Mattoon South

Quality Inn & Suites Mattoon South

10/10 Excellent
"Check in was fast, staff very nice, room was clean. Great price "
joshua 1-night trip
Posted 2 days ago
Quality Inn & Suites Mattoon South