Windsor Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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.
The price is AEDĀ 294
AEDĀ 436 total
includes taxes & fees
15 Nov - 16 Nov
Cozy, and private apartment near Lake Shelbyville
An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

2. 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.
The price is AEDĀ 441
AEDĀ 868 total
includes taxes & fees
1 Dec - 2 Dec
Fish, boat, grill, chill, pets, relax
A brick house with a white door, a mailbox, and a wooden porch.

3. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (54 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is AEDĀ 404
AEDĀ 635 total
includes taxes & fees
19 Nov - 20 Nov
Brickway Retreat
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

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.
The price is AEDĀ 315
AEDĀ 455 total
includes taxes & fees
14 Nov - 15 Nov
Cozy 1-bedroom with AC and WiFi in charming Shelbyville
A compact kitchen with wooden cabinets, a refrigerator, a stove, and two bar stools.

5. 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.
The price is AEDĀ 661
AEDĀ 973 total
includes taxes & fees
23 Nov - 24 Nov
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
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.
The price is AEDĀ 612
AEDĀ 874 total
includes taxes & fees
14 Nov - 15 Nov
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.
The price is AEDĀ 573
AEDĀ 926 total
includes taxes & fees
30 Nov - 1 Dec
Prairieview Cabin - with Hot Tub
A rustic cabin with a porch, surrounded by a well-maintained lawn and trees.

8. Binion Lodge: Wooded Privacy Near Lake Shelbyville

Binion Lodge: Wooded Privacy Near Lake Shelbyville
Sullivan Township
10.0 out of 10, Exceptional, (20 reviews)
"Very nice and secluded property! Hosts are outstanding as well!"
United States
John
The price is AEDĀ 845
AEDĀ 1,535 total
includes taxes & fees
23 Nov - 24 Nov
Binion Lodge: Wooded Privacy Near Lake Shelbyville
A modern kitchen with a central island, dark cabinetry, and a ceiling fan.

9. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (62 reviews)
"Very clean and cute place! We enjoyed our stay very much. The hosts were wonderful, and we even got the blessing of a visit by the 2 puppies that live on the property. Definitely recommend staying here! "
United States
Lisa S.
The price is AEDĀ 691
AEDĀ 1,255 total
includes taxes & fees
1 Dec - 2 Dec
Prairieview Cottage Retreat - Hot Tub Sunsets
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

10. 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
The price is AEDĀ 1,035
AEDĀ 1,567 total
includes taxes & fees
7 Dec - 8 Dec
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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Find vacation rentals that suit your style

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Top Windsor Hotel Reviews

A hotel room with a large bed, a separate desk with a chair, a TV, a bathroom with a bathtub, and a window with curtains.
Comfort Suites Mattoon East

Comfort Suites Mattoon East

Comfort Suites Mattoon East
Mattoon

10/10 Excellent

Great, comfortable stay. Clean. Good breakfast!
United States
Sandy
Reviewed November 8, 2026
Comfort Suites Mattoon East

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.