Windsor Vacation Rentals from $148: 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 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.

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Our top choices for Windsor vacation rentals

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

Windsor

$172 nightly

Sep 27 - Sep 28

Total with taxes and fees

2. Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

Neoga

$256 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Sullivan

Samuel D S.

$268 nightly

Oct 1 - Oct 2

Total with taxes and fees

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

Sullivan

aubrey m.

$263 nightly

Sep 21 - Sep 22

Total with taxes and fees

5. Brickway Retreat

Mattoon

Kevin F.

$170 nightly

Oct 6 - Oct 7

Total with taxes and fees

6. Cozy, and private apartment near Lake Shelbyville

Shelbyville

Brandon S.

$140 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

Shelbyville

Rosanne D.

$145 nightly

Sep 22 - Sep 23

Total with taxes and fees

8. Prairieview Cabin - with Hot Tub

Sullivan

Brandon R.

$260 nightly

Sep 28 - Sep 29

Total with taxes and fees

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Top Windsor Hotel Reviews

The Shelby Inn

10/10 Excellent

"It was comfortable and clean."

Suite Dreams Hotel

8/10 Good

"This was a fine place to stay for a simple overnight. (I stayed here to sleep before catching a 4 a.m. train.) The room itself was comfortable--not luxurious, but clean and everything worked. Two issues to be aware of: there is a very large internal atrium that is conspicuously not air conditioned and was VERY hot when I checked in on a hot day. (The room AC worked fine.) Also, the stairway to the second floor was steep and pretty dark during the evening and night. There was no light source directly above it. This could be dangerous if you have mobility issues or a lot of luggage. (I do not believe there is an elevator.) The hotel seems to cater to utility workers, etc., but as a single older woman I never felt unsafe at the hotel or the vicinity."

Best Western Heartland Inn

10/10 Excellent

"We had such a great experience during my stay! Paige at the front desk was absolutely amazing and incredibly helpful. She made sure everything went smoothly and went above and beyond to make our stay comfortable and enjoyable. Her customer service really stood out, and she made the whole experience feel easy and stress-free. I would 10/10 recommend this hotel to anyone looking for a great stay and staff who actually care about making sure everything is taken care of. Paige definitely made our experience even better! ⭐️⭐️⭐️⭐️⭐️"

Quality Inn & Suites Mattoon South

8/10 Good

"The staff was extremely helpful and friendly. Check in was great. Water pressure was just ok. Our toilet really didn’t flush well and the tv would not work. In the end not a deal breaker. We were tired and just went to bed early. It was quiet and the room was clean and comfortable."

Gateway Inn

8/10 Good

"With all the great reviews, I was expecting it to be immaculate and well maintained. That was not my experience. It was very comfortable and relatively clean. Staff were friendly and helpful. Full disclosure, my opinion could be slightly skewed because, for some reason, I thought the place was much closer to Effingham - but it was 45 minutes away adding an extra hour and a half to my trip. But that is NOT the hotel’s fault - I just didn’t check all the details closely enough on Expedia. But still, it was a solid 4."

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10/10 Excellent

"Vicky's place was great! The fishing ponds kept my husband busy. A short drive to Shelbyville for food, recreation and fun. The firepit was nice. There wasn't anyone at the camping sites so that was a plus. House was clean, kitchen had the basics. Beds were firm. The screened in porch was fantastic!"

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 $148 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. Wolf Creek State Park 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

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

2. Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

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

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

5. Brickway Retreat

6. Cozy, and private apartment near Lake Shelbyville

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

8. Prairieview Cabin - with Hot Tub

9. Binion Lodge: Wooded Privacy Near Lake Shelbyville

10. Prairieview Cottage Retreat - Hot Tub Sunsets

11. Family Friendly Cottage in the Countryside

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

The Shelby Inn

Suite Dreams Hotel

Best Western Heartland Inn

Spillway Motel

Quality Inn & Suites Mattoon South

Gateway Inn

Eagle's Nest near Eagle Creek State Park

Prairieview Cabin - with Hot Tub

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

Find out more about Windsor

Frequently asked questions

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