Default HTG hotel image

Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windsor vacation rentals

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

1. 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 ￥28,438
￥44,035 total
includes taxes & fees
Oct 30 - Oct 31
Lakeside Haven Come enjoy the relaxing stay next to the Lake with nature sounds
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.
The price is ￥17,379
￥28,465 total
includes taxes & fees
Oct 29 - Oct 30
Brickway Retreat
An aerial view of Lake Shelbyville with RVs, a large building, and a bridge in the background.

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

Fish, boat, grill, chill, pets, relax
Sullivan
9.4 out of 10, Exceptional, (72 reviews)
"It was excellent!"
United States
Samuel D S.
The price is ￥24,172
￥45,039 total
includes taxes & fees
Oct 29 - Oct 30
Fish, boat, grill, chill, pets, relax
A residential street with a house featuring a front porch, outdoor seating, and string lights.

4. 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 ￥15,749
￥23,368 total
includes taxes & fees
Nov 8 - Nov 9
Cozy, and private apartment near Lake Shelbyville
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, (19 reviews)
"Place was great!"
United States
Robyn J.
The price is ￥13,021
￥20,310 total
includes taxes & fees
Oct 29 - Oct 30
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.
The price is ￥26,222
￥41,310 total
includes taxes & fees
Nov 10 - Nov 11
Eagle's Nest near Eagle Creek State Park
A rustic cabin with a porch, surrounded by a well-maintained lawn and trees.

7. 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 ￥36,338
￥69,359 total
includes taxes & fees
Nov 23 - Nov 24
Binion Lodge: Wooded Privacy Near Lake Shelbyville
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

8. 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 ￥24,967
￥42,006 total
includes taxes & fees
Nov 17 - Nov 18
Prairieview Cabin - with Hot Tub
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 nice everything was perfect couldn't have asked for a better time recommend very much"
United States
Ben D.
The price is ￥32,100
￥59,551 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥40,710
￥66,723 total
includes taxes & fees
Oct 29 - Oct 30
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Comfort Suites Mattoon East

Comfort Suites Mattoon East

10/10 Excellent
"This was hands down the best room I've stayed in since I started driving a truck. I wish I had more downtime to relax in there. Room was great. Staff was knowledgeable about the area. Comfort Suites is my new go to when I have to stop driving for the night."
Thomas 1-night trip
Posted 14 hours ago
Comfort Suites Mattoon East

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
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.