Windsor Vacation Homes

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

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Our top choices for Windsor holiday homes

A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

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

Bridgeview

Abby M.

HK$853 total

includes taxes & fees

26 Oct - 27 Oct

A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

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

South Windsor

Mohamad C.

HK$1,392 total

includes taxes & fees

19 Oct - 20 Oct

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

3. 3 bdr upper, prime location

Remington Park

HK$1,624 total

includes taxes & fees

31 Oct - 1 Nov

A single-story house with a front porch, a mailbox, and a number "627" on the wall.

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

Walkerville

Valerie C.

HK$1,932 total

includes taxes & fees

8 Nov - 9 Nov

A couple in a hot tub with candles, wooden walls, and windows.

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

City Centre

Trent Y.

HK$1,848 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a large island, stainless steel sink, and white cabinetry.

6. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

HK$901 total

includes taxes & fees

9 Nov - 10 Nov

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.

7. The Windsor Loft

Bridgeview

HK$1,461 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Bridgeview

HK$1,079 total

includes taxes & fees

2 Nov - 3 Nov

A modern living room with a fireplace, a large flat-screen TV, a mirror, and a round coffee table with decorative plants.

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

Devonshire

Junwu

A modern kitchen with white cabinets, stainless steel appliances, and a central island.

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

Devonshire

Tony

HK$1,351 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a leather sofa, a coffee table, and a TV mounted on the wall.

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

Walkerville

Nicole C.

HK$2,574 total

includes taxes & fees

15 Nov - 16 Nov

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

12. Cozy 2 Bedroom Luxury Suite

Roseland

Lindsay M.

HK$1,082 total

includes taxes & fees

19 Oct - 20 Oct

13. Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,

East Windsor

HK$1,499 total

includes taxes & fees

22 Oct - 23 Oct

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

14. 7BR house 19 ppl DT Windsor Free Parking

City Centre

Mark D.

HK$4,810 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a sectional sofa, a coffee table, and a large window offering a view of greenery.

15. Premium Stay Near Windsor Employers & Hospital

Ford City

Adam Y.

HK$1,819 total

includes taxes & fees

20 Oct - 21 Oct

16. Fully Furnished 2 bedroom basement in Windsor

Walkerville

"The home owner was incredibly nice and accommodating. They even picked us up from the train station nearby, and answered any msg quickly. I really appreciated that. Great neighborhood. The actual apartment wasn't quite what was advertised, the place wasn't as classy as the vrbo pictures. Also i thought vrbo was all about having a place to yourself? I was woken up a few times by footsteps upstairs where the owner lives. No laundry detergent, no bbq, 1 1/2 rolls of tp provided. Not worth the cost...

Kirk

HK$1,161 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

Roseland

Dannavan C.

HK$2,653 total

includes taxes & fees

19 Oct - 20 Oct

A staircase with a chandelier, a potted plant, and a mirror reflecting the room.

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

Roseland

Mohammed M.

HK$7,877 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with two sofas, a coffee table, and artwork on the walls.

19. The Windsor Mainstay

Bridgeview

HK$2,120 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

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

Devonshire

Tamarah M.

HK$2,736 total

includes taxes & fees

19 Oct - 20 Oct

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Top Windsor Hotel Reviews

Hyatt Place Windsor

10/10 Excellent

"Last minute reservation for this hotel and it was a nice upgrade from the previous hotel we stayed in. Highly recommend and we will be back next time we visit Windsor."

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

10/10 Excellent

"Took awhile to find the elevators to go up to the second floor. Very long walk from parking garage to the registration desk. We will probably go back when we get another good deal on our room. Otherwise we stay off the property which means we are in the casino as long."

Super 8 by Wyndham Ambassador Bridge Windsor ON

8/10 Good

"The breakfast options could be a bit better. Especially the fruit choices. I think if more fresh varieties of fruit were offered people would like that. The bananas were greenish. But these things are not easy to run, i get that as well. I'm always happy there. Its clean and reasonably priced"

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