Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Windsor vacation rentals

Exterior detail

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (41 reviews)
"This house was perfect! Very clean, beautifully decorated and very cozy. So many nice extras. Because of bad weather we had to modify our stay and we were very grateful that the hosts were able to accommodate us. We would absolutely stay here again. "
United States
Shari
$170 nightly
The price is $180
Jan 20 - Jan 21
Total with taxes and fees
Brickway Retreat
Smart TV, fireplace

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, (27 reviews)
"Great place! "
United States
Luis G.
$236 nightly
The price is $250
Jan 20 - Jan 21
Total with taxes and fees
Cozy Country Cabin - Sleeps 6 - with Hot Tub
Interior

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Sullivan
10.0 out of 10, Exceptional, (51 reviews)
"It was a wonderful stay. We loved the location and the patio during the evening!"
United States
Lyndsey C.
$314 nightly
The price is $332
Jan 22 - Jan 23
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8
Exterior detail

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, (8 reviews)
"Place was great!"
United States
Robyn J.
$122 nightly
The price is $129
Jan 20 - Jan 21
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Fridge, microwave, oven, stovetop

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon

Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Mattoon
10.0 out of 10, Exceptional, (2 reviews)
"Property was perfect, nice quiet location. One night stay option was perfect for what we needed."
United States
Chad S.
$248 nightly
The price is $263
Jan 20 - Jan 21
Total with taxes and fees
Greenwave Cottage-Fully furnished 3 Bedroom home on the west edge of Mattoon
Property grounds

Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville
Shelbyville
9.6 out of 10, Exceptional, (20 reviews)
"Great place and location for visiting Lake Shelbyville "
United States
Kenneth G.
$140 nightly
The price is $148
Feb 1 - Feb 2
Total with taxes and fees
Cozy, and private apartment near Lake Shelbyville
Interior

Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park
Findlay
9.4 out of 10, Exceptional, (17 reviews)
"Amazing host and property. "
United States
Nicholas K.
$200 nightly
The price is $212
Jan 21 - Jan 22
Total with taxes and fees
Eagle's Nest near Eagle Creek State Park
Exterior

Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.6 out of 10, Exceptional, (60 reviews)
"really enjoyed out stay here"
United States
Linda B.
$251 nightly
The price is $266
Jan 20 - Jan 21
Total with taxes and fees
Fish, boat, grill, chill, pets, relax
Microwave, oven, stovetop, dishwasher

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds

Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
2.0 star property
Sullivan
$261 nightly
The price is $277
Jan 20 - Jan 21
Total with taxes and fees
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
Exterior

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (14 reviews)
"Great very quiet and relaxing awesome property and host"
United States
Tyler R.
$399 nightly
The price is $427
Jan 21 - Jan 22
Total with taxes and fees
Binion Lodge: Wooded Privacy 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

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

10/10 Excellent
"Great experience. "
James W. 4-night trip
Posted 8 days ago
Prairieview Cottage Retreat - Hot Tub Sunsets - Sleeps 8

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?

Cozy Refurbished Cottage Near Lake Shelbyville - Pet & Boat Friendly: This vacation home rental near Windsor is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly.

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. Mattoon City Hall and Eagle 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.