Windsor Vacation Rentals

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Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
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Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Windsor

Cozy, and private apartment near Lake Shelbyville
Interior

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."
$140 nightly
The price is $148
Sep 30 - Oct 1
Total with taxes and fees
Cozy, and private apartment near Lake Shelbyville
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, (17)
"Great place! "
$253 nightly
The price is $268
Sep 10 - Sep 11
Total with taxes and fees
Cozy Country Cabin - Sleeps 6 - with Hot Tub
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
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, (37)
"This is definitely a repeat location for a girls’ getaway weekend. Quiet, clean, and equipped with all of the amenities. "
$327 nightly
The price is $347
Sep 18 - Sep 19
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Exterior

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
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. "
$122 nightly
The price is $129
Sep 8 - Sep 9
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
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
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.
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!
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
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
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
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."
$170 nightly
The price is $180
Sep 8 - Sep 9
Total with taxes and fees
Brickway Retreat
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)
"Amazing host and property. "
$233 nightly
The price is $247
Sep 22 - Sep 23
Total with taxes and fees
Eagle's Nest near Eagle Creek State Park
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)
"Enjoyed the house very much! It is a sweet little house, but has everything you might need. "
Come Escape to Paradise on the Lake
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
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Exterior

Binion Lodge: Wooded Privacy Near Lake Shelbyville

10.0 out of 10, Exceptional, (14)
"Everything was clean and comfortable, with nice space"
$406 nightly
The price is $437
Sep 9 - Sep 10
Total with taxes and fees
Binion Lodge: Wooded Privacy Near Lake Shelbyville
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Fridge, microwave, oven, stovetop

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."
$244 nightly
The price is $259
Sep 20 - Sep 21
Total with taxes and fees
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
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

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 $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

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 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.