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

Windsor Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Windsor vacation rentals

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

1. Windsor Manor

City Centre

Jacob

CA $436 total

includes taxes & fees

Nov 18 - Nov 19

A kitchen with a stainless steel refrigerator, a double sink, and a backsplash of gray tiles.

2. Windsor 1BR + Office | Business & Midterm Stays

Walkerville

harchetan

CA $250 total

includes taxes & fees

Nov 9 - Nov 10

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

3. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

City Centre

Stacy A.

CA $221 total

includes taxes & fees

Nov 17 - Nov 18

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

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

Bridgeview

Abby M.

CA $154 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a grey sofa, a white coffee table, and a flat-screen TV on a wooden stand.

5. Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

Walkerville

Mary M.

CA $148 total

includes taxes & fees

Nov 9 - Nov 10

A hotel room with a large bed, two windows with curtains, a view of the city, and a small plant.

6. Walkerville 2BR Suite | Near Casino & Free Parking

Walkerville

Aidan

CA $316 total

includes taxes & fees

Nov 9 - Nov 10

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

7. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

CA $152 total

includes taxes & fees

Nov 29 - Nov 30

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

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

Walkerville

Valerie C.

CA $337 total

includes taxes & fees

Nov 16 - Nov 17

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

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

South Windsor

Mohamad C.

CA $238 total

includes taxes & fees

Nov 10 - Nov 11

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

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

City Centre

Trent Y.

CA $336 total

includes taxes & fees

Nov 9 - Nov 10

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.

CA $445 total

includes taxes & fees

Nov 9 - Nov 10

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

12. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

East Windsor

Kruz

CA $175 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Devonshire

Pauline

CA $473 total

includes taxes & fees

Nov 9 - Nov 10

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 $310 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living room with a black sofa, large windows, a flat-screen TV, and a dining area with a marble countertop.

15. Penthouse suite in heart of little Italy

Walkerville

Chris A.

CA $420 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

16. Beautiful gem with amazing view on the riverside

Bridgeview

Jenni T.

CA $245 total

includes taxes & fees

Nov 10 - Nov 11

A hallway with a marble floor, a bed in the background, and a wall with circular patterns.

17. Clean and spacious 3BR DT Windsor Laundry and parking

City Centre

CA $309 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Devonshire

Tony

CA $231 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a blue sofa, grey armchairs, and a glass coffee table. There are framed pictures on the wall and a window with curtains.

19. Stylish 2bd DT Laundry and Parking

City Centre

CA $266 total

includes taxes & fees

Nov 15 - Nov 16

A narrow hallway with a refrigerator on the left, a door at the end, and a wall calendar on the right.

20. Cozy King Suite

Walkerville

CA $203 total

includes taxes & fees

Nov 9 - Nov 10

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Find vacation rentals that suit your style

Top Windsor Hotel Reviews

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

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 staircase with a dark wooden handrail and a patterned carpet.

Sandwich Boutique Hotel

Sandwich

10/10 Excellent

Tom

A modern lounge area with seating, a fireplace, and a television.

Hampton Inn & Suites by Hilton Windsor

South Cameron

10/10 Excellent

Wayne

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

Alison

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 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 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

A reception desk with a sign reading "Quality Inn & Suites by Choice".

Quality Inn & Suites Downtown Windsor

Downtown Windsor

10/10 Excellent

Shyann

An indoor swimming pool with clear water, surrounded by lounge chairs and a seating area with tables.

Comfort Inn & Suites Ambassador Bridge

South Cameron

10/10 Excellent

Greg

A modern living room with grey sofas, a stone accent wall, and large windows offering a view of the outdoors.

Super 8 by Wyndham Windsor/Dougall

Remington Park

10/10 Excellent

Lisa

Windsor Manor

City Centre

10/10 Excellent

Dino

A hotel room with a large bed, a cityscape painting, a green-tiled jacuzzi, and a nightstand with a lamp.

Super 8 by Wyndham Ambassador Bridge Windsor ON

Sandwich

10/10 Excellent

Pierre

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Adventure Bay Family Water Park, or you can go with a secluded option if you want a relaxing stay. Visitors to Windsor speak positively about the scenic riverfront and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and live music.

What are some of the best vacation rentals in Windsor?

Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking: Visitors give good reviews to this Windsor vacation home rental, which offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden. Some other homes for rent in Windsor include 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9 and Paradise Home - Your Home Away From Home.

How many vacation rentals will I find in Windsor?

With 111 Expedia vacation rentals, you're sure to find just the right place for your Windsor stay.

What’s there to see and do in Windsor?

Family-friendly attractions include Adventure Bay Family Water Park and Olde Walkerville Neighborhood, whereas Windsor Riverfront and East Riverside Park are a couple of great spots to enjoy the outdoors. You’ll find favorite places to visit like Ford Field and Little Caesars Arena in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are private properties you can book for short or long periods in Windsor. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips.

Windsor Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor vacation rentals

1. Windsor Manor

2. Windsor 1BR + Office | Business & Midterm Stays

3. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

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

5. Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

6. Walkerville 2BR Suite | Near Casino & Free Parking

7. Cozy Modern Walkerville Basement Apartment

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

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

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

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

12. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

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

14. Premium Stay Near Windsor Employers & Hospital

15. Penthouse suite in heart of little Italy

16. Beautiful gem with amazing view on the riverside

17. Clean and spacious 3BR DT Windsor Laundry and parking

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

19. Stylish 2bd DT Laundry and Parking

20. Cozy King Suite

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Ye Olde Walkerville Bed & Breakfast

10/10 Excellent

Find out more about Windsor

Windsor vacation rentals: An excellent choice for every season

How to find incredible deals on Windsor rentals

Frequently Asked Questions

Are there vacation rentals in Windsor?

What are some of the best vacation rentals in Windsor?

How many vacation rentals will I find in Windsor?

What’s there to see and do in Windsor?

What’s a vacation rental in Windsor like?

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