Windsor Vacation Rentals from $129: Search Short-Term Rentals

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

Fish, boat, grill, chill, pets, relax : This vacation home 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.

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Our top choices for Windsor vacation rentals

Brickway Retreat

Mattoon

VINCENT

$170 nightly

Apr 13 - Apr 14

Total with taxes and fees

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Shelbyville

Jim B.

$122 nightly

Apr 13 - Apr 14

Total with taxes and fees

Prairieview Cabin - with Hot Tub

Sullivan

Ana Rosa R.

$260 nightly

Apr 13 - Apr 14

Total with taxes and fees

Eagle's Nest near Eagle Creek State Park

Findlay

Nicholas K.

$240 nightly

Apr 13 - Apr 14

Total with taxes and fees

Fish, boat, grill, chill, pets, relax

Sullivan

Kevin P.

$268 nightly

Apr 13 - Apr 14

Total with taxes and fees

Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Windsor

$160 nightly

Apr 19 - Apr 20

Total with taxes and fees

Cozy, and private apartment near Lake Shelbyville

Shelbyville

Brandon S.

$140 nightly

Apr 15 - Apr 16

Total with taxes and fees

Prairieview Cottage Retreat - Hot Tub Sunsets

Sullivan

Lyndsey C.

$352 nightly

Apr 13 - Apr 14

Total with taxes and fees

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Sullivan Township

Tyler R.

$387 nightly

Apr 14 - Apr 15

Total with taxes and fees

Country Comfort House • Relax, Recharge, Repeat

Sullivan

$220 nightly

Apr 13 - Apr 14

Total with taxes and fees

The Emerald Escape: Moody emerald loft near the lake.

Shelbyville

"The major issue we had was that the internet was not working the entire time of our stay. We had a short stay (one day two nights) and I contacted the host as soon as we arrived for wifi info. He gave it to us, and our devices said connected, but no internet available. We spent a couple of hours trying different things with no luck while communicating with the host. We finally ended up using our phones as hotspots for that evening. The next day I contacted them again, and got no response until I...

Alison G.

$140 nightly

Apr 13 - Apr 14

Total with taxes and fees

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Top Windsor Hotel Reviews

Best Western Heartland Inn

10/10 Excellent

"Friendly staff, clean and quiet room, would stay there again."

Quality Inn & Suites Mattoon South

8/10 Good

"The hotel was older and lots of little things wrong, but nothing terrible. Beds were clean and comfortable, breakfast was decent but limited. We just needed a place that we could stop overnight on a long trip with our dog and this place was perfect for that and a good price. We would stop there again, but it’s not nice enough for a vacation stay of several days. "

The Emerald Escape: Moody emerald loft near the lake.

4/10 Poor

"The major issue we had was that the internet was not working the entire time of our stay. We had a short stay (one day two nights) and I contacted the host as soon as we arrived for wifi info. He gave it to us, and our devices said connected, but no internet available. We spent a couple of hours trying different things with no luck while communicating with the host. We finally ended up using our phones as hotspots for that evening. The next day I contacted them again, and got no response until I sent a message asking for the internet issue to be addressed immediately. They brought a hotspot within an hour that worked for another few hours, then that quit as well. At that point we gave up. We spent at least a 3-4 hours of our "relaxing" 42 hour getaway trying to troubleshoot on our own and communicating with the host/waiting for responses. This was supposed to be a relaxing weekend where my husband and I could just hang out, play online and watch movies. We were really disappointed that wasn't a possibility. Secondly, there was an issue in the apartment of a paint or lacquer smell that was headache inducing when the door to the gold room wasn't closed. There were some other minor issues (tiny shower, having to move lamps around to get ideal lighting, had to get towels out of the dryer before showering, no check-in/out guide) that would have totally been overlooked if not for the internet and smell problems, but combined, it made for a really disappointing stay."

The Shelby Inn

10/10 Excellent

"We stayed at the Shelby Inn overnight Easter Sunday night, after a day of fishing at the lake spillway. The Inn looks to be a mansion in pictures, but it is also what might have been an upgraded 1950s single floor motor lodge, as well as a two story lodging building next door. Our king room was in the 2 story building, on the top floor. On the day of our arrival, we got the assigned room number and an access code for the door. The room was well appointed, spacious with a two-seater table and chairs, dish TV,, the shower had a rainfall shower head, and dispensers for private brand shampoo, conditioner, and body wash. Everything was very clean and welcoming. Parking was off street, open parking lot betwren the buildings. It was 40° and 30 mph winds, so we didn't have any concern about air conditioning, but the heat was very effective and warmed us right up. When we come back to Shelbyville, we will definitely be staying here. (Since we were in town on Easter Sunday and didn't get back to town from the spillway until after 8:00, there wasn't much beyond fast food that was still open. I can definitely recommend Oliver Coffee, a neat little drive-thru-only coffee shop that we visited Monday am,, and heard great things from others about the Lakeview Family Restaurant.)"

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.

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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 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 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.

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Check prices for these dates

Our top choices for Windsor vacation rentals

Brickway Retreat

Cozy 1-bedroom with AC and WiFi in charming Shelbyville

Prairieview Cabin - with Hot Tub

Eagle's Nest near Eagle Creek State Park

Fish, boat, grill, chill, pets, relax

Off grid cabin adjacent to Corp of Engineers ground. Perfect Deer Camp

Cozy, and private apartment near Lake Shelbyville

Prairieview Cottage Retreat - Hot Tub Sunsets

Binion Lodge: Wooded Privacy Near Lake Shelbyville

Country Comfort House • Relax, Recharge, Repeat

The Emerald Escape: Moody emerald loft near the lake.

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Best Western Heartland Inn

Quality Inn & Suites Mattoon South

The Emerald Escape: Moody emerald loft near the lake.

Comfort Suites Mattoon East

The Shelby Inn

Hilton Garden Inn Mattoon, Il

Holiday Inn Express & Suites Mattoon by IHG

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

Clarion Pointe Mattoon near University

Find out more about Windsor

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