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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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

Windsor Manor
4.0 star property
City Centre
10.0 out of 10, Exceptional, (3 reviews)
"Facility was spotless. There were no staff members on site"
Canada
Jacob
$246 nightly
The price is $294
Nov 5 - Nov 6
Total with taxes and fees
Windsor Manor
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.

2. Stylish 2bd DT Laundry and Parking

Stylish 2bd DT Laundry and Parking
City Centre
$163 nightly
The price is $188
Nov 8 - Nov 9
Total with taxes and fees
Stylish 2bd DT Laundry and Parking
A modern living room with a grey sofa, a round coffee table, and a dining area with a black table and chairs.

3. Quaint Clean 2BR DT Windsor Laundry and parking Inc

Quaint Clean 2BR DT Windsor Laundry and parking Inc
City Centre
2.0 out of 10, (1 review)
"We must state that this place was very clean, the sheets and towels smelled nice, and the beds were comfortable; however, it is a very old basement where only a furnace and root cellar should be located. The floor is all uneven and multi levels, it is very poorly finished, we had zero control of the heat, and there are no useable windows. The table is very rickety. The site photos are deceiving; we were not impressed, and it was very over-priced for the lack of quality."
United States
Sandra H.
$156 nightly
The price is $181
Nov 5 - Nov 6
Total with taxes and fees
Quaint Clean 2BR DT Windsor Laundry and parking Inc
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.

Affordable 1BHK close to Riverside, Casino, University & USA Border.
Bridgeview
9.4 out of 10, Exceptional, (3 reviews)
"Nice place, good location, host was nice and helpful"
United States
Abby M.
$98 nightly
The price is $111
Nov 16 - Nov 17
Total with taxes and fees
Affordable 1BHK close to Riverside, Casino, University & USA Border.
A modern living room with a fireplace, a sofa, a coffee table, and a dining area.

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

Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
City Centre
10.0 out of 10, Exceptional, (12 reviews)
"We loved our quick stay at Casa Rio - cute, comfortable, and equipped with anything we needed, very close to the river walk, just blocks from the casino, fun restaurants and bars. Great experience - will come back again!"
United States
Stacy A.
$136 nightly
The price is $154
Nov 9 - Nov 10
Total with taxes and fees
Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel
A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

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

Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Bridgeview
$115 nightly
The price is $130
Nov 5 - Nov 6
Total with taxes and fees
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

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

Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
South Windsor
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful stay "
United States
Mohamad C.
$151 nightly
The price is $170
Nov 10 - Nov 11
Total with taxes and fees
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
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

🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
Walkerville
8.8 out of 10, Excellent, (20 reviews)
"Great communication with host, clean, convenient parking and excellent location for events at Caesars!"
United States
Valerie C.
$210 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
A modern kitchen with a large island, stainless steel sink, and white cabinetry.

9. Cozy Modern Walkerville Basement Apartment

Cozy Modern Walkerville Basement Apartment
Walkerville
10.0 out of 10, Exceptional, (1 review)
"It was a nice clean place to spend the weekend."
United States
Robin W.
$94 nightly
The price is $111
Nov 16 - Nov 17
Total with taxes and fees
Cozy Modern Walkerville Basement Apartment
A kitchen with a stainless steel refrigerator, a double sink, and a backsplash of gray tiles.

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

Windsor 1BR + Office | Business & Midterm Stays
Walkerville
10.0 out of 10, Exceptional, (1 review)
"Wonderful property with all amenities provided . The neighborhood is equally nice and safe."
Canada
harchetan
$162 nightly
The price is $183
Nov 9 - Nov 10
Total with taxes and fees
Windsor 1BR + Office | Business & Midterm Stays
A couple in a hot tub with a view of a house and street outside.

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

Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
City Centre
9.0 out of 10, Wonderful, (2 reviews)
"Great stay! Walking distance to all the things in the area."
United States
Trent Y.
$213 nightly
The price is $240
Nov 16 - Nov 17
Total with taxes and fees
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
A kitchen with a stainless steel refrigerator, a black faucet, a paper towel holder, and a knife block.

12. Stay Together but with Privacy of Two Fully Equipped Apartments

Stay Together but with Privacy of Two Fully Equipped Apartments
Walkerville
$260 nightly
The price is $293
Nov 5 - Nov 6
Total with taxes and fees
Stay Together but with Privacy of Two Fully Equipped Apartments
A modern living room with a glass table, grey sofas, and a staircase leading to a service area.

13. Windsor Perfect Stay

Windsor Perfect Stay
Remington Park
$88 nightly
The price is $104
Nov 8 - Nov 9
Total with taxes and fees
Windsor Perfect Stay
A modern living room with a sofa, coffee table, and dining area.

14. 3 bdr upper, prime location

3 bdr upper, prime location
Remington Park
$162 nightly
The price is $183
Nov 8 - Nov 9
Total with taxes and fees
3 bdr upper, prime location
A hotel room with a large bed, two windows with curtains, a view of the city, and a small plant.

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

Walkerville 2BR Suite | Near Casino & Free Parking
Walkerville
10.0 out of 10, Exceptional, (3 reviews)
"Great place for a little weekend stay. Host was friendly and got back to me fast with any answers to my questions. No problems checking in or out. Overall a great stay"
United States
Aidan
$207 nightly
The price is $234
Nov 8 - Nov 9
Total with taxes and fees
Walkerville 2BR Suite | Near Casino & Free Parking
A modern kitchen with white cabinets, a microwave, stove, and two bar stools.

16. Walkerville 1BR Suite | Parking, Laundry & WiFi

Walkerville 1BR Suite | Parking, Laundry & WiFi
Walkerville
Walkerville 1BR Suite | Parking, Laundry & WiFi
A modern living room with a grey sofa, a white coffee table, and a flat-screen TV on a wooden stand.

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

Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
Walkerville
9.0 out of 10, Wonderful, (2 reviews)
"Very clean, beautiful home, and the host, Yolanda, is amazing with communication:)"
United States
Mary M.
$103 nightly
The price is $116
Nov 9 - Nov 10
Total with taxes and fees
Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4
A covered outdoor area with a wooden deck, a basketball, and a view of a residential neighborhood.

18. Cozy King Suite

Cozy King Suite
Walkerville
$129 nightly
The price is $145
Nov 6 - Nov 7
Total with taxes and fees
Cozy King Suite
A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

19. Beautiful gem with amazing view on the riverside

Beautiful gem with amazing view on the riverside
Bridgeview
10.0 out of 10, Exceptional, (1 review)
"This is a great little apartment, right across from the river and the Sculpture Park, with amazing views of the sunset and the Ambassador Bridge. The apartment was very clean and the bed was very comfortable. The location is ideal! The host was very quick to respond. Thank you Hyatt for a great experience!"
United States
Jenni T.
$155 nightly
The price is $175
Nov 5 - Nov 6
Total with taxes and fees
Beautiful gem with amazing view on the riverside
A modern living room with a grey sofa, wooden coffee table, and a dining area with a small table and chairs.

20. Cozy 2 Bedroom Luxury Suite

Cozy 2 Bedroom Luxury Suite
Roseland
10.0 out of 10, Exceptional, (1 review)
"We had a great stay! The place was very clean, comfortable, and in a great location with everything we needed nearby."
Canada
Lindsay M.
$103 nightly
The price is $116
Nov 5 - Nov 6
Total with taxes and fees
Cozy 2 Bedroom Luxury Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Comfort Inn South Windsor

Comfort Inn South Windsor

10/10 Excellent
"I liked the cleanliness and organization of my room, as well as the breakfast selection. They also have a pantry where you can buy quick snacks if you don't have any, which I also took advantage of."
Nicholas 1-night trip
Posted 6 hours ago
Comfort Inn South Windsor

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.