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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Windsor vacation rentals

A residential street with a house featuring a front porch, outdoor seating, and string lights.

1. Cozy, and private apartment near Lake Shelbyville

Cozy, and private apartment near Lake Shelbyville
Shelbyville
9.8 out of 10, Exceptional, (24 reviews)
"Excellent stay. Very nice accommodations. Will absolutely be staying there again the next time we are in town. "
United States
Brandon S.
$112 nightly
The price is $119
Nov 5 - Nov 6
Total with taxes and fees
Cozy, and private apartment near Lake Shelbyville
A brick house with a white door, a mailbox, and a wooden porch.

2. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
$162 nightly
The price is $172
Nov 8 - Nov 9
Total with taxes and fees
Brickway Retreat
A spacious kitchen with wooden cabinets, a dishwasher, and a dining area with a table and chairs.

3. Fish, boat, grill, chill, pets, relax

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (72 reviews)
"The house was clean. Beds and couches were very comfortable. Great for our dogs."
United States
Vince S.
$222 nightly
The price is $235
Dec 1 - Dec 2
Total with taxes and fees
Fish, boat, grill, chill, pets, relax
A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

4. 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
Sullivan
9.4 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay. It was close proximity to the beach on Lake Shelbyville and the property was clean."
United States
aubrey m.
$272 nightly
The price is $288
Nov 23 - Nov 24
Total with taxes and fees
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
A house with a porch supported by white columns, a black door with a wreath, and two white rocking chairs.

5. Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Cozy 1-bedroom with AC and WiFi in charming Shelbyville
Shelbyville
8.4 out of 10, Very good, (20 reviews)
"Place was great!"
United States
Robyn J.
$114 nightly
The price is $120
Nov 5 - Nov 6
Total with taxes and fees
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
A kitchen with a marble countertop, stainless steel refrigerator, and wooden cabinets.

6. Eagle's Nest near Eagle Creek State Park

Eagle's Nest near Eagle Creek State Park
Findlay
9.6 out of 10, Exceptional, (26 reviews)
"Me and my family loved this place. Very clean. We enjoyed our stay and would stay again."
United States
terri m.
$225 nightly
The price is $238
Nov 5 - Nov 6
Total with taxes and fees
Eagle's Nest near Eagle Creek State Park
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

7. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (47 reviews)
"Very nice place to stay!"
United States
Brandon R.
$249 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
Prairieview Cabin - with Hot Tub
A modern kitchen with a central island, dark cabinetry, and a ceiling fan.

8. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (62 reviews)
"Very nice everything was perfect couldn't have asked for a better time recommend very much"
United States
Ben D.
$340 nightly
The price is $342
Dec 1 - Dec 2
Total with taxes and fees
Prairieview Cottage Retreat - Hot Tub Sunsets
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

9. Family Friendly Cottage in the Countryside

Family Friendly Cottage in the Countryside
Toledo
10.0 out of 10, Exceptional, (3 reviews)
"Super clean and quiet was a great place to get away while visiting family and friends."
United States
Richard
$425 nightly
The price is $427
Nov 25 - Nov 26
Total with taxes and fees
Family Friendly Cottage in the Countryside
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
"Everything was great!"
Joe 2-night trip
Posted 19 hours 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 $119 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.

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?

Fish, boat, grill, chill, pets, relax: This vacation home rental near Windsor is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the arcade game room 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. Mattoon City Hall 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.