A city skyline with a prominent casino building, a tall skyscraper, and several other high-rise buildings along a waterfront.

Windsor Holiday 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor holiday rentals

A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

1. Windsor Manor

Windsor Manor
4.0 star property
City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Facility was spotless. There were no staff members on site"
Canada
Jacob
The price is HK$480
HK$2,347 total
includes taxes & fees
18 Oct - 19 Oct
Windsor Manor
A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

2. Affordable 1BHK close to Riverside, Casino, University & USA Border.

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
9.0 out of 10, Wonderful, (2 reviews)
"Nice place, good location, host was nice and helpful"
United States
Abby M.
The price is HK$423
HK$838 total
includes taxes & fees
20 Oct - 21 Oct
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A modern living room with a blue sofa, grey armchairs, and a glass coffee table. There are framed pictures on the wall and a window with curtains.

3. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
The price is HK$459
HK$1,547 total
includes taxes & fees
19 Oct - 20 Oct
Stylish 2bd DT Laundry and Parking
A hallway with a marble floor, a bed in the background, and a wall with circular patterns.

4. Clean and spacious 3BR DT Windsor Laundry and parking

Clean and spacious 3BR DT Windsor Laundry and parking
City Centre
The price is HK$663
HK$1,992 total
includes taxes & fees
12 Nov - 13 Nov
Clean and spacious 3BR DT Windsor Laundry and parking
A modern living room with a fireplace, a sofa, a coffee table, and a dining area.

5. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
City Centre
10.0 out of 10, Exceptional, (12 reviews)
"We loved our quick stay at Casa Rio - cute, comfortable, and equipped with anything we needed, very close to the river walk, just blocks from the casino, fun restaurants and bars. Great experience - will come back again!"
United States
Stacy A.
The price is HK$692
HK$1,335 total
includes taxes & fees
2 Nov - 3 Nov
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

6. 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Walkerville
8.8 out of 10, Excellent, (20 reviews)
"Great communication with host, clean, convenient parking and excellent location for events at Caesars!"
United States
Valerie C.
The price is HK$628
HK$1,895 total
includes taxes & fees
9 Nov - 10 Nov
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A modern living room with a sofa, coffee table, and dining area.

7. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is HK$719
HK$1,614 total
includes taxes & fees
10 Nov - 11 Nov
3 bdr upper, prime location
A modern living room with a sectional sofa, a round coffee table, a flat-screen TV mounted on the wall, and a large abstract painting on the wall.

8. The Windsor Loft

The Windsor Loft
Bridgeview
The price is HK$989
HK$1,453 total
includes taxes & fees
19 Oct - 20 Oct
The Windsor Loft
A couple in a hot tub with candles, wooden walls, and windows.

9. Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
City Centre
9.0 out of 10, Wonderful, (2 reviews)
"Great stay! Walking distance to all the things in the area."
United States
Trent Y.
The price is HK$722
HK$1,971 total
includes taxes & fees
10 Nov - 11 Nov
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A hotel room with a large bed, two windows with curtains, a view of the city, and a small plant.

10. Walkerville 2BR Suite | Near Casino & Free Parking

Walkerville 2BR Suite | Near Casino & Free Parking
Walkerville
10.0 out of 10, Exceptional, (3 reviews)
"Great place for a little weekend stay. Host was friendly and got back to me fast with any answers to my questions. No problems checking in or out. Overall a great stay"
United States
Aidan
Walkerville 2BR Suite | Near Casino & Free Parking
A kitchen with a stainless steel refrigerator, a black faucet, a paper towel holder, and a knife block.

11. Stay Together but with Privacy of Two Fully Equipped Apartments

Stay Together but with Privacy of Two Fully Equipped Apartments
Walkerville
The price is HK$749
HK$2,348 total
includes taxes & fees
11 Nov - 12 Nov
Stay Together but with Privacy of Two Fully Equipped Apartments
A living room with a blue sofa, a round wooden coffee table with a plant, a lamp, and a painting on the wall.

12. Walkerville 1BR | WiFi + Workspace + Parking

Walkerville 1BR | WiFi + Workspace + Parking
Walkerville
The price is HK$521
HK$1,514 total
includes taxes & fees
20 Oct - 21 Oct
Walkerville 1BR | WiFi + Workspace + Parking
A modern living room with a flat-screen TV mounted on the wall, a glass coffee table, and a grey sofa.

13. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
East Windsor
9.4 out of 10, Exceptional, (6 reviews)
"Amazing stay, Very clean and nice inside. Host is also nice and easy to communicate with."
Canada
Kruz
The price is HK$604
HK$904 total
includes taxes & fees
12 Nov - 13 Nov
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

14. Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit

Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Bridgeview
The price is HK$516
HK$1,074 total
includes taxes & fees
13 Nov - 14 Nov
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A room with a closed door, a set of drawers, and a small window.

15. Cozy King Suite

Cozy King Suite
Walkerville
The price is HK$594
HK$1,194 total
includes taxes & fees
26 Oct - 27 Oct
Cozy King Suite
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

16. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
South Windsor
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful stay "
United States
Mohamad C.
The price is HK$764
HK$1,385 total
includes taxes & fees
15 Oct - 16 Oct
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A residential area with houses, a parking lot, and a large building with a grey roof.

17. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
The price is HK$545
HK$877 total
includes taxes & fees
20 Oct - 21 Oct
Windsor Perfect Stay
A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

18. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
The price is HK$687
HK$1,422 total
includes taxes & fees
13 Nov - 14 Nov
Beautiful gem with amazing view on the riverside
A spacious living room with a leather sofa, a coffee table, and a TV mounted on the wall.

19. Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !

Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Walkerville
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place to stay. Great location....perfect for two couples. Nice space indoors and outdoors."
United States
Nicole C.
The price is HK$1,511
HK$2,555 total
includes taxes & fees
14 Oct - 15 Oct
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
A modern kitchen with a large island, stainless steel sink, and white cabinetry.

20. Cozy Modern Walkerville Basement Apartment

Cozy Modern Walkerville Basement Apartment
Walkerville
10.0 out of 10, Exceptional, (1 review)
"It was a nice clean place to spend the weekend."
United States
Robin W.
The price is HK$471
HK$900 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Modern Walkerville Basement Apartment
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

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

10/10 Excellent
"Place was nice much better than I expected for the money especially I will return there another time"
Jeff 1-night trip
Posted 8 hours ago
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

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 holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Adventure Bay Family Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windsor speak positively about the scenic riverfront and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and live music.

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

Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking: This highly rated holiday home rental in Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. Some other homes for rent in Windsor include 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9 and Paradise Home - Your Home Away From Home.

How many holiday rentals will I find in Windsor?

With 111 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What’s there to see and do in Windsor?

Family-friendly attractions include Adventure Bay Family Water Park and Olde Walkerville Neighborhood, whereas Windsor Riverfront and East Riverside Park are a couple of great spots to enjoy the outdoors. You’ll find favourite places to visit such as Ford Field and Little Caesars Arena in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.