Windsor Vacation Rentals

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Dec 26 - Dec 28

Vacation Rentals in Windsor

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

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

10.0 out of 10, Exceptional, (2)
"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.
Cozy Country Cabin - Sleeps 6 - with Hot Tub
Exterior

Cozy Country Cabin - Sleeps 6 - with Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (18)
"Great place! "
$253 nightly
The price is $268
Oct 6 - Oct 7
Total with taxes and fees
Cozy Country Cabin - Sleeps 6 - with Hot Tub
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

9.6 out of 10, Exceptional, (4)
"Stayed here before...always nice "
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Historic 1850's downtown home, located downtown, very close to Lake Shelbyville.
Interior

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
Outdoor dining

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

10.0 out of 10, Exceptional, (39)
"Love this place if we come to IL again we will love to stay at Paraview cottage Retreat I love the country and was so relaxing the stay was great this place was beautiful!!"
$333 nightly
The price is $353
Oct 9 - Oct 10
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Lake Mattoon Lakehouse
Microwave, oven, stovetop, dishwasher

Lake Mattoon Lakehouse

9.4 out of 10, Exceptional, (14)
"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
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Exterior

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (28)
"Beautiful property. Couldn’t be better. "
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Brickway Retreat
Fridge, microwave, oven, stovetop

Brickway Retreat

9.8 out of 10, Exceptional, (37)
"All was more than expected. We definitely stay again.Best accommodations we had in Mattoon. "
$170 nightly
The price is $180
Oct 6 - Oct 7
Total with taxes and fees
Brickway Retreat
Paradise Found in Illinois
Fridge, microwave, oven, stovetop

Paradise Found in Illinois

10.0 out of 10, Exceptional, (172)
"Property was nice. Very relaxing. House had everything you could need"
Paradise Found in Illinois
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, (12)
"Great stay! "
Come Escape to Paradise on the Lake
Eagle's Nest near Eagle Creek State Park
Fridge, microwave, oven, stovetop

Eagle's Nest near Eagle Creek State Park

9.2 out of 10, Wonderful, (14)
"Amazing host and property. "
$200 nightly
The price is $212
Oct 3 - Oct 4
Total with taxes and fees
Eagle's Nest near Eagle Creek State Park
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Fridge, microwave, coffee/tea maker, toaster

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

8.0 out of 10, Very Good, (4)
"First time on this side. Wonderful stay. Close to everything. The bed is so comfy. "
$125 nightly
The price is $132
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
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, (22)
"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
Fridge, microwave, oven, stovetop

Fish, boat, grill, chill, pets, relax

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. "
Fish, boat, grill, chill, pets, relax
Lake Shelbyville Country Cottage w/ Hot Tub - 5 minutes from Lake
Outdoor dining

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
Newly updated and cozy home! Located near downtown!
Interior

Newly updated and cozy home! Located near downtown!

9.0 out of 10, Wonderful, (14)
"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!
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Exterior

Binion Lodge: Wooded Privacy Near Lake Shelbyville

10.0 out of 10, Exceptional, (14)
"This place is awesome! My granddaughters had a ball in the game room. We loved that it was also pet friendly. "
$406 nightly
The price is $437
Oct 20 - Oct 21
Total with taxes and fees
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
House (3 Bedrooms) | Interior

Woodsy Home w/ View, 1 Mi to Lake Shelbyville

3.0 star property
Woodsy Home w/ View, 1 Mi to Lake Shelbyville
Cozy, and private apartment near Lake Shelbyville
Interior

Cozy, and private apartment near Lake Shelbyville

9.6 out of 10, Exceptional, (15)
"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."
$140 nightly
The price is $148
Oct 6 - Oct 7
Total with taxes and fees
Cozy, and private apartment near Lake 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

Quality Inn & Suites Mattoon South

Quality Inn & Suites Mattoon South

10/10 Excellent
"Will stay here again "
Jayne 2-night trip
Posted 2 days ago
Quality Inn & Suites Mattoon South

Find out more about Windsor

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 $132 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

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?

Wooded rural country estate near Lake Shelbyville and Illinois Amish country: This vacation home rental near Windsor is located on a lake and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 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.