Windsor Holiday Rentals: Short-Term Accommodations for Rent

Q: What are some of the best holiday rentals that Windsor has to offer?

Fish, boat, grill, chill, pets, relax : This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of an arcade/games room in this rental home to help you unwind.

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Our top choices for Windsor holiday rentals

A cozy cabin interior with a wooden dining table, metal chairs, a small basket, and a window with a view of trees.

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

Windsor

HK$1,413 total

includes taxes & fees

4 Oct - 5 Oct

A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

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

Sullivan

aubrey m.

HK$2,078 total

includes taxes & fees

29 Sept - 30 Sept

An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

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

Sullivan

Samuel D S.

HK$2,145 total

includes taxes & fees

1 Oct - 2 Oct

A house with a porch supported by white columns, a black door with a wreath, and two white rocking chairs.

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

Shelbyville

Rosanne D.

HK$1,012 total

includes taxes & fees

29 Sept - 30 Sept

A kitchen with a marble countertop, stainless steel refrigerator, and wooden cabinets.

5. Eagle's Nest near Eagle Creek State Park

Findlay

Michelle B.

HK$2,120 total

includes taxes & fees

20 Oct - 21 Oct

A spacious living area with a large window, a television, and a dining table.

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

Neoga

HK$2,030 total

includes taxes & fees

29 Sept - 30 Sept

A brick house with a white door, a mailbox, and a wooden porch.

7. Brickway Retreat

Mattoon

Kevin F.

HK$1,413 total

includes taxes & fees

6 Oct - 7 Oct

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

8. Cozy, and private apartment near Lake Shelbyville

Shelbyville

Brandon S.

HK$1,164 total

includes taxes & fees

4 Oct - 5 Oct

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Top Windsor Hotel Reviews

The Shelby Inn

10/10 Excellent

"SPACIOUS ROOM, EASY PARKING, QUIET & SAFE"

Clarion Pointe Mattoon near University

10/10 Excellent

"Absolutely the cleanest hotel we've been to in many years! Very friendly staff both at check in and when we left. I was doing a horse training clinic and worked for 2-1/2 hours straight after travelling 8 hours from Ohio and my legs were very tired and hurt badly, the huge tub was clean enough to suit me and I took a long soak in it. Hats off to the whole crew and Keep up the good work!"

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! ⭐️⭐️⭐️⭐️⭐️"

Prairieview Cabin - with Hot Tub

10/10 Excellent

"I loved staying at this cabin! Everything was absolutely perfect, ambience, cleanly, had everything I could need and more! The view of the pond during morning coffee and the hot tub with the sunset set the bar high. The bed was super comfy and overall very cozy cabin. Located close to Sullivan and within 20ish mins to the lake. I went to Wolf beach and had a great time! I will be back. Rose was wonderful as well!"

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."

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

View our selection of featured holiday rentals in Windsor
Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What are some of the best holiday rentals that Windsor has to offer?

Fish, boat, grill, chill, pets, relax: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of an arcade/games 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 wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family trips.

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Check prices for these dates

Our top choices for Windsor holiday rentals

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

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

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

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

5. Eagle's Nest near Eagle Creek State Park

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

7. Brickway Retreat

8. Cozy, and private apartment near Lake Shelbyville

9. Binion Lodge: Wooded Privacy Near Lake Shelbyville

10. Prairieview Cabin - with Hot Tub

11. Prairieview Cottage Retreat - Hot Tub Sunsets

12. Family Friendly Cottage in the Countryside

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

The Shelby Inn

Clarion Pointe Mattoon near University

Quality Inn & Suites Mattoon South

Suite Dreams Hotel

Best Western Heartland Inn

Paradise Found in Illinois

Spillway Motel

Prairieview Cabin - with Hot Tub

Gateway Inn

Find out more about Windsor

Frequently asked questions

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