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

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

South Windsor

Mohamad C.

HK$1,396 total

includes taxes & fees

3 Nov - 4 Nov

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.

Bridgeview

Abby M.

HK$845 total

includes taxes & fees

16 Nov - 17 Nov

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

3. 3 bdr upper, prime location

Remington Park

HK$1,633 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$1,942 total

includes taxes & fees

26 Oct - 27 Oct

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$2,024 total

includes taxes & fees

5 Nov - 6 Nov

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

6. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

HK$903 total

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

HK$1,081 total

includes taxes & fees

3 Nov - 4 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.

8. The Windsor Loft

Bridgeview

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

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$2,606 total

includes taxes & fees

2 Nov - 3 Nov

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.

A two-story residential building with a front porch, a wooden fence, and a paved driveway.

13. Premium Stay Near Windsor Employers & Hospital

Ford City

Adam Y.

HK$1,823 total

includes taxes & fees

1 Nov - 2 Nov

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

14. Cozy 2 Bedroom Luxury Suite

Roseland

Lindsay M.

HK$1,084 total

includes taxes & fees

3 Nov - 4 Nov

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

HK$1,164 total

includes taxes & fees

3 Nov - 4 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.

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

Roseland

Dannavan C.

HK$2,565 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Roseland

Mohammed M.

HK$7,902 total

includes taxes & fees

3 Nov - 4 Nov

A modern dining area with a marble table, white chairs, and a vase of flowers.

18. The Windsor Mainstay

Bridgeview

HK$2,137 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Devonshire

Pauline

A neatly made bed with a white comforter and pillows, a wooden floor, and a window with dark curtains.

20. Little Belle River home

Belle River

Mike

HK$785 total

includes taxes & fees

22 Oct - 23 Oct

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Top Windsor Hotel Reviews

Comfort Inn & Suites Ambassador Bridge

8/10 Good

"Room was very clean, staff was very helpfull, good room service."

DoubleTree by Hilton Windsor Hotel & Suites

8/10 Good

"The hotel was clean, the beds were very comfortable, and most attractions were within walking distance. My only disappointment was the parking experience. I hadn’t realized parking cost extra, and the directions led to a frustrating back-and-forth. A staff member insisted there was no parking structure with a DoubleTree sign, then described the exact structure displaying that sign. I didn’t appreciate the argumentative exchange. Clearer parking information and a more courteous response would have made an otherwise enjoyable stay much better."

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