Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Windsor

Exterior
Cozy Country Cabin - Sleeps 6 - with Hot Tub

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
Sullivan
10.0 out of 10, Exceptional, (23)
"The cabin was clean and had all the amenities needed for an escape from society. Its far enough from town to feel secluded but close enough that you can easily drive in to grab essentials. The hot tub was clean and a preheated for our stay. The hardest part about the entire stay was leaving. It felt nice to get away for a few days. "
United States
Kelly
$236 nightly
The price is $250
Nov 18 - Nov 19
Total with taxes and fees
Cozy Country Cabin - Sleeps 6 - with Hot Tub
Outdoor dining
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Sullivan
10.0 out of 10, Exceptional, (46)
"This property is beautiful, we had a great time relaxing at this comfortable cottage. "
United States
Michael C.
$333 nightly
The price is $353
Nov 18 - Nov 19
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Game room
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!

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

Findlay
10.0 out of 10, Exceptional, (25)
"We had a great time in this lovely location. The back patio was wonderful and we enjoyed spending time in the evening out there!"
United States
Yvonne H.
Ultimate Country Home with a 4800 sq.ft shed- pickle ball, corn hole, and more!!
Fridge, microwave, oven, stovetop
Brickway Retreat

Brickway Retreat

Mattoon
9.8 out of 10, Exceptional, (38)
"Nice and clean home. "
United States
Kelly J.
$170 nightly
The price is $180
Nov 19 - Nov 20
Total with taxes and fees
Brickway Retreat
Exterior
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.

Shelbyville
9.2 out of 10, Wonderful, (5)
"Perfect Spot for a Bestie Getaway! We found this gem for our annual bestie trip, and it was perfect! The location couldn’t be better, right by Lithia Springs Marina (literally 2 min drive). Nichole was amazing from the start, super helpful and friendly. The house is beautifully decorated and thoughtfully stocked with everything you could need.We grilled on the Blackstone, soaked in the hot tub, and had a blast with outdoor Jenga and cornhole. The kids loved spotting deer every day! There was...
United States
Jennifer B.
A Novel Stay 3bd log cabin with Hot tub in amazing Shelbyville, IL. 3.5 acres.
Fridge, microwave, oven, stovetop
Spacious 5-bedroom Home Centrally Located-Sleeps 14!

Spacious 5-bedroom Home Centrally Located-Sleeps 14!

2.0 star property
Shelbyville
Spacious 5-bedroom Home Centrally Located-Sleeps 14!
Fridge, microwave, oven, stovetop
Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park

Findlay
9.2 out of 10, Wonderful, (15)
"Amazing host and property. "
United States
Nicholas K.
$203 nightly
The price is $215
Nov 19 - Nov 20
Total with taxes and fees
Eagle's Nest near Eagle Creek State Park
Fridge, microwave, oven, stovetop
Paradise Found in Illinois

Paradise Found in Illinois

Mattoon
10.0 out of 10, Exceptional, (172)
"We have stayed here several times. We enjoy observing the seasonal changes and the birdlife. It's a cozy retreat."
United States
Richard and Rhonda
Paradise Found in Illinois
Fridge, microwave, oven, stovetop
Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax

Sullivan
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. "
United States
Audrey M.
$248 nightly
The price is $263
Nov 30 - Dec 1
Total with taxes and fees
Fish, boat, grill, chill, pets, relax
Interior
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.

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

Shelbyville
9.4 out of 10, Exceptional, (45)
"Nice accommodations for what we needed."
United States
Anita W.
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
Exterior
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

Lakewood
10.0 out of 10, Exceptional, (31)
"Beautiful property. Couldn’t be better. "
United States
Michael s.
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Property grounds
Come Escape to Paradise on the Lake

Come Escape to Paradise on the Lake

2.0 star property
Mattoon
10.0 out of 10, Exceptional, (13)
"Enjoyed the house very much! It is a sweet little house, but has everything you might need. "
United States
pankey128@yahoo.com P.
Come Escape to Paradise on the Lake
Property grounds
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds

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

Lakewood
9.8 out of 10, Exceptional, (6)
"Check-in was smooth, very nice property. Kitchen nice and roomy as well as rest of house had all we needed for our long weekend trip. We grilled, relaxed on deck over looking ponds and fished here a lil. Not to mention fun days on lake and at beach. We will definitely be back!"
United States
Anastasia C.
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Interior
Newly updated and cozy home! Located near downtown!

Newly updated and cozy home! Located near downtown!

Mattoon
9.2 out of 10, Wonderful, (15)
"It was conveniently located near the train station and restaurants. The host was always quick to respond to inquiries. "
United States
Linda M.
Newly updated and cozy home! Located near downtown!
Exterior
Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Sullivan Township
10.0 out of 10, Exceptional, (14)
"Peaceful, beautiful place"
United States
Maria G.
$377 nightly
The price is $405
Nov 24 - Nov 25
Total with taxes and fees
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Interior
Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville

Shelbyville
9.6 out of 10, Exceptional, (19)
"Location😁 App coordination between Expedia and Vrbo😒"
United States
Paul
$140 nightly
The price is $148
Nov 18 - Nov 19
Total with taxes and fees
Cozy, and private apartment near Lake Shelbyville
Outdoor dining
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake

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

Shelbyville
9.8 out of 10, Exceptional, (26)
"Overall great space. Plenty of room and outdoor space was top notch. "
United States
Sean W.
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
House (3 Bedrooms) | Interior
Woodsy Home w/ View, 1 Mi to Lake Shelbyville

Woodsy Home w/ View, 1 Mi to Lake Shelbyville

3.0 star property
Shelbyville
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Smart TV
Cozy Country Home Near Lake Shelbyville

Cozy Country Home Near Lake Shelbyville

Sullivan
Cozy Country Home Near Lake Shelbyville
Fridge, microwave, coffee/tea maker, toaster
Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Shelbyville
8.8 out of 10, Excellent, (6)
"On our way to the property, they messaged us to say that they had double booked the unit we had reserved and that we would have to stay in a different unit. Second and much bigger problem was that the AC did not work. When we got there we turned the thermostat down as it read 80 at our arrival. The outside temperature at the time was in the mid-90s. Two hours later it still was at 80 when we had turned it down to 70 earlier. We then messaged the host to let him know. He assured us it would cool...
United States
Mindye M.
$122 nightly
The price is $129
Nov 18 - Nov 19
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
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

Comfort Suites Mattoon East

Comfort Suites Mattoon East

10/10 Excellent
"Clean hotel. Good breakfast, pool area was clean, super helpful staff. "
Samantha 2-night trip
Posted 5 days ago
Comfort Suites Mattoon East

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we have vacation rentals close to the most popular sights in Windsor, or you can choose a more remote option if you're looking for relaxation. Windsor is known for its restaurants and shopping.

What are some of the best vacation home rentals in Windsor?

Eagle's Nest near Eagle Creek State Park: This vacation home rental near Windsor is located on a lake and has a patio, a barbecue grill, 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 Mattoon City Hall are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.