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

Holiday Homes in Windsor

  • 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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Windsor holiday homes

A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

1. 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 NZ$239
includes taxes & fees
21 Sept - 22 Sept
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
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.
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A single-story house with a front porch, a mailbox, and a number "627" on the wall.

3. 🎰🚶‍♂️ 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 NZ$450
includes taxes & fees
21 Sept - 22 Sept
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
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.

4. The Windsor Loft

The Windsor Loft
Bridgeview
The price is NZ$299
includes taxes & fees
21 Sept - 22 Sept
The Windsor Loft
A modern living room with a sofa, coffee table, and dining area.

5. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
The price is NZ$418
includes taxes & fees
8 Sept - 9 Sept
3 bdr upper, prime location
A couple in a hot tub with candles, wooden walls, and windows.

6. 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
10.0 out of 10, Exceptional, (1 review)
"Great stay! Walking distance to all the things in the area."
United States
Trent Y.
The price is NZ$463
includes taxes & fees
21 Sept - 22 Sept
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A laundry room with a stacked washer and dryer, a trash bin, and a coffee maker on a counter.

7. Cozy 2-bedroom house in fantastic Windsor with AC

Cozy 2-bedroom house in fantastic Windsor with AC
Forest Glade
"Sheet with house rules when you arrive indicating that you could not drink on property. Dirty used razor left in the shower. House is not private owner lives upstairs and there was no privacy as a sheet separated the upstairs from the downstairs. The host was friendly and communicated well."
Canada
Karen
The price is NZ$217
includes taxes & fees
8 Sept - 9 Sept
Cozy 2-bedroom house in fantastic Windsor with AC
A modern living room with a sectional sofa, a coffee table, and a large window providing a view of greenery outside.

8. New 4BR |Main Floor -Ensuite |Group & Family |Free Parking | Weekend & Long-Stay

New 4BR |Main Floor -Ensuite |Group & Family |Free Parking | Weekend & Long-Stay
Ford City
8.8 out of 10, Excellent, (8 reviews)
"Everything was as describe in profile we made some amazing memories in this house and will return when we come back to visit!"
United States
Carla
The price is NZ$374
includes taxes & fees
8 Sept - 9 Sept
New 4BR |Main Floor -Ensuite |Group & Family |Free Parking | Weekend & Long-Stay
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

9. Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Devonshire
9.0 out of 10, Wonderful, (11 reviews)
"Home was very clean, good location close to major amenities, Devonshire mall, Costco. Easy access via key pad, ample parking. "
Canada
Tony
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

10. 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.
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
A modern kitchen with a large island, stainless steel sink, and white cabinetry.

11. 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 NZ$250
includes taxes & fees
21 Sept - 22 Sept
Cozy Modern Walkerville Basement Apartment
A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

12. Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.

Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Devonshire
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay. The host was very responsive and addressed any issues quickly. The property was very clean, and the location was very convenient. Would definitely stay again."
Canada
Junwu
The price is NZ$299
includes taxes & fees
8 Oct - 9 Oct
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
A spacious living room with a leather sofa, a coffee table, and a TV mounted on the wall.

13. 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 NZ$573
includes taxes & fees
8 Sept - 9 Sept
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
A modern kitchen with dark wood cabinets, stainless steel appliances, and a marble backsplash. There are two bar stools and a small island with a sink.

14. Modern Spacious 1 bedroom and a den home (Lower Unit)

Modern Spacious 1 bedroom and a den home (Lower Unit)
Roseland
8.0 out of 10, Very good, (9 reviews)
"was a great property and location"
United States
Ava C.
The price is NZ$582
includes taxes & fees
8 Sept - 9 Sept
Modern Spacious 1 bedroom and a den home (Lower Unit)
A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

15. 7BR house 19 ppl DT Windsor Free Parking

7BR house 19 ppl DT Windsor Free Parking
City Centre
4.0 out of 10, (1 review)
"The main floor refrigerator didn’t work and the roof leaked when it rained all over the master bed through the ceiling fan."
United States
Mark D.
7BR house 19 ppl DT Windsor Free Parking
A modern dining area with a marble table, white chairs, and a vase of flowers.

16. The Windsor Mainstay

The Windsor Mainstay
Bridgeview
The price is NZ$467
includes taxes & fees
21 Sept - 22 Sept
The Windsor Mainstay
A staircase with a chandelier, a potted plant, and a mirror reflecting the room.

17. Luxury getaway with pool and hot tub - family retreat

Luxury getaway with pool and hot tub - family retreat
Roseland
7.2 out of 10, Good, (5 reviews)
"We didn’t get bothered at all but parking was tight and should let guest know there are people downstairs "
Canada
Matthew K.
The price is NZ$1,708
includes taxes & fees
8 Sept - 9 Sept
Luxury getaway with pool and hot tub - family retreat
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

18. Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest
Devonshire
10.0 out of 10, Exceptional, (1 review)
"Thank you for the stay, the house was amazing. Very clean quiet and family friendly! We had a great time and tired to leave the place how we found it. Thanks sm for a great stay"
United States
Tamarah M.
The price is NZ$601
includes taxes & fees
8 Sept - 9 Sept
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest

19. Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups

Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups
Windsor
Spacious 3BR Basement Suite | Near 5min Gordie Howe Bridge | Families & Groups
A neatly made bed with a white comforter and pillows, a wooden floor, and a window with dark curtains.

20. Little Belle River home

Little Belle River home
Belle River
9.8 out of 10, Exceptional, (9 reviews)
"My wife and I were very happy with our stay. We will definitely come back the next time we’re in the area."
Canada
GJ D.
The price is NZ$173
includes taxes & fees
14 Sept - 15 Sept
Little Belle River home
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

DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

10/10 Excellent
"This was a great place to stay"
Mia 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Windsor Hotel & Suites

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
82
Accommodation
155 Holiday Homes
Lowest Price
NZ$173
Highest Price
NZ$1,708