Windsor Holiday Homes from €93: Search Top House Rentals

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.

includes taxes & fees

20 Oct - 21 Oct

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

2. 3 bdr upper, prime location

Remington Park

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

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

South Windsor

Mohamad C.

includes taxes & fees

13 Nov - 14 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.

includes taxes & fees

19 Oct - 20 Oct

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.

5. The Windsor Loft

Bridgeview

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✨

City Centre

Trent Y.

includes taxes & fees

2 Nov - 3 Nov

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

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

Bridgeview

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

8. Cozy 2 Bedroom Luxury Suite

Roseland

Lindsay M.

includes taxes & fees

18 Oct - 19 Oct

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

includes taxes & fees

18 Oct - 19 Oct

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

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

Walkerville

Nicole C.

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

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

Devonshire

Tony

includes taxes & fees

18 Oct - 19 Oct

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

12. 7BR house 19 ppl DT Windsor Free Parking

City Centre

Mark D.

includes taxes & fees

19 Oct - 20 Oct

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

13. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

includes taxes & fees

15 Nov - 16 Nov

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

14. Premium Stay Near Windsor Employers & Hospital

Ford City

Adam Y.

includes taxes & fees

20 Oct - 21 Oct

15. 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

includes taxes & fees

1 Nov - 2 Nov