Windsor Vacation Home Rentals from CA $75: Search Top Private Vacation Homes for Rent

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Our top choices for Windsor vacation 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

Laurie

CA $144 total

includes taxes & fees

Dec 1 - Dec 2

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

2. 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleep 10

Walkerville

Valerie C.

CA $332 total

includes taxes & fees

Nov 25 - Nov 26

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.

CA $240 total

includes taxes & fees

Nov 18 - Nov 19

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

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

City Centre

Trent Y.

CA $407 total

includes taxes & fees

Nov 30 - Dec 1

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

5. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

CA $153 total

includes taxes & fees

Dec 1 - Dec 2

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

6. 3 bdr upper, prime location

Remington Park

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

John P.

CA $183 total

includes taxes & fees

Nov 16 - Nov 17

8. 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

CA $198 total

includes taxes & fees

Nov 16 - Nov 17

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

East Windsor

mariah m.

CA $351 total

includes taxes & fees

Nov 16 - Nov 17

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.

CA $445 total

includes taxes & fees

Nov 16 - Nov 17

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

11. 7BR house 19 ppl DT Windsor Free Parking

City Centre

Mark D.

CA $831 total

includes taxes & fees

Nov 19 - Nov 20

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.

Devonshire

Junwu

CA $232 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Devonshire

Tony

CA $232 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a sofa, coffee table, and a view of the outside.

14. Premium Stay Near Windsor Employers & Hospital

Ford City

Adam Y.

CA $311 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a grey sofa, a coffee table, and a large flat-screen TV mounted on the wall.

15. The Windsor Mainstay

Bridgeview

rose h.

CA $368 total

includes taxes & fees

Nov 17 - Nov 18

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.

CA $340 total

includes taxes & fees

Nov 16 - Nov 17

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.

CA $730 total

includes taxes & fees

Nov 16 - Nov 17

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

Devonshire

Pauline

CA $473 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with white cabinetry, a central island, and a coffee bar sign.

19. Executive One-Bedroom Upper Unit

Windsor

Mary

CA $194 total

includes taxes & fees

Nov 22 - Nov 23

A hot tub with a wooden fence and trees in the background.

20. 14th Coffee Co. Homestead Farmhouse

Essex

Barbara P.

CA $339 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Windsor and related destinations

Directly across from Detroit, this riverside city offers stunning waterfront parks and the historic Walkerville district with local distilleries. Visitors can explore the colourful sculptures at Odette Sculpture Park or catch performances at the magnificent Capitol Theatre when they're not sampling poutine at local eateries.

See all hotels in Windsor

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

Top reviews in Windsor

Hotel STRY

Amherstburg

10/10 Excellent

Leslie

A Holiday Inn Express hotel with a modern design, featuring a large parking lot and a well-maintained exterior.

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

Lakeshore

10/10 Excellent

Angel

A room with two beds, a forest mural, starry ceiling, and a window with natural light.

The Grove Motel

Essex

10/10 Excellent

Philip

A cozy living room with a tufted sofa, a floral rug, a Christmas tree, and a painting on the wall.

Ye Olde Walkerville Bed & Breakfast

Walkerville

10/10 Excellent

The owner is very welcoming and the minute you walk in, you feel the old world charm: from the decor to the homemade cookies that are under glass. I had to leave early and was sad that I would miss what was probably a great breakfast but the charming owner prepared a lunch bag that I could take with me and was amazed by the size, quality that the bag contained. I will rent from her again if I go back Windsor way.

Daniel

An indoor swimming pool with a city view, lounge chairs, and a tiled deck.

DoubleTree by Hilton Windsor Hotel & Suites

Downtown Windsor

10/10 Excellent

faiza

A staircase with a dark wooden handrail and a patterned carpet.

Sandwich Boutique Hotel

Sandwich

10/10 Excellent

Tom

An outdoor patio area with seating, a grill, and a fire feature.

TownePlace Suites by Marriott Windsor

Downtown Windsor

10/10 Excellent

This hotel is perfect for an extended stay. It was quiet, yet close to everything we needed. After a long drive in, the riverfront is just a short walk away if you want to stretch your legs while taking in the downtown Detroit skyline. The more recently renovated room was spacious, with a variety of seating areas, nicely decorated, and comfortable bed. Every single hotel employee we encountered had a kind word and was so welcoming. Everyone was very helpful, warm, and genuine. It really made...

Anonymous traveller

A hotel room with a large bed, a desk, a TV, and a view of a city skyline.

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

City Centre

10/10 Excellent

Lorena

A multi-story hotel with a prominent entrance and a Holiday Inn Express sign.

Holiday Inn Express Windsor Waterfront by IHG

Downtown Windsor

10/10 Excellent

Daniel

A modern cafe with tables and chairs, a counter with food items, and a view of the outside.

Comfort Inn South Windsor

South Windsor

10/10 Excellent

Andrew

A spacious lobby with a modern design, featuring a large seating area, a fireplace, and a bar/lounge area with a brick accent wall.

Four Points by Sheraton Windsor Downtown

Downtown Windsor

10/10 Excellent

Jolene M

A hotel room with a bed, bedside tables, a desk, a chair, and a bathroom visible through an open door.

Kenora Motel

South Cameron

10/10 Excellent

We frequently visit family in Windsor and have stayed in both airbnb and hotels and Kenora motel is among the best. The rooms are large and modern. Everything is fresh and very clean. The beds are super comfortable, the shower good. Nice large tv and both fridge and microwave to keep and heat up food. For us the location was perfect coming off the 401 from Toronto and central to most places. We will definitely come back.

Susanne