Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Windsor vacation rentals

Full-size fridge, microwave, oven, stovetop
Windsor Manor

Apartment in City Centre

4.0 star property
$250 nightly
The price is $300
Dec 10 - Dec 11
Total with taxes and fees
Windsor Manor
Fridge, microwave, oven, stovetop
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

Vacation Home in South Windsor

10.0 out of 10, Exceptional, (14)
"Great stay! "
Canada
Jade S.
$160 nightly
The price is $181
Dec 12 - Dec 13
Total with taxes and fees
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
Fridge, microwave, stovetop, dishwasher
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

Apartment in East Windsor

9.0 out of 10, Wonderful, (2)
"Very beautiful home! We were originally unaware that the accommodations were on the host’s property however since they were separate from the main house it barely made a difference. Overall a very relaxing and clean stay!"
United States
Deianira B.
$87 nightly
The price is $98
Dec 15 - Dec 16
Total with taxes and fees
6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style
Interior
Modern 3‑BR Riverside Retreat, 2 Lounges, Near Casino & Riverfront.

Apartment in Riverside

10.0 out of 10, Exceptional, (3)
"My friends and I had a great stay here, and it was super spacious!"
United States
Samantha R.
$217 nightly
The price is $245
Dec 12 - Dec 13
Total with taxes and fees
Modern 3‑BR Riverside Retreat, 2 Lounges, Near Casino & Riverfront.
Fridge, microwave, oven, stovetop
Cozy comfort lower level unit

Vacation Home in Roseland

9.8 out of 10, Exceptional, (9)
"We enjoyed our stay very much."
Canada
Amanda
$103 nightly
The price is $117
Dec 12 - Dec 13
Total with taxes and fees
Cozy comfort lower level unit
Fridge, microwave, oven, stovetop
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

Vacation Home in Devonshire

8.8 out of 10, Excellent, (5)
"This stay exceeded our expectations. Would definitely recommend."
Canada
Natalie
$147 nightly
The price is $166
Dec 12 - Dec 13
Total with taxes and fees
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Fridge, microwave, oven, stovetop
Modern Spacious 1 bedroom and a den home (Lower Unit)

Vacation Home in Roseland

8.4 out of 10, Very Good, (6)
"was a great property and location"
United States
Ava C.
$213 nightly
The price is $241
Dec 12 - Dec 13
Total with taxes and fees
Modern Spacious 1 bedroom and a den home (Lower Unit)
Smart TV, fireplace
Cozy 2 Bdrm, Lounge w/fpl, Kitchenette, TV, Wi-Fi

Vacation Home in East Riverside

9.4 out of 10, Exceptional, (3)
"I was in town to visit family so this location was great"
United States
nancy K.
$168 nightly
The price is $189
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy 2 Bdrm, Lounge w/fpl, Kitchenette, TV, Wi-Fi
Fridge, microwave, oven, stovetop
Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests

Vacation Home in Walkerville

9.2 out of 10, Wonderful, (14)
"My car got broken into during the night but great stay besides that "
United States
Katie W.
$201 nightly
The price is $228
Jan 7 - Jan 8, 2026
Total with taxes and fees
Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests
Interior
Clean and spacious 3BR DT Windsor Laundry and parking

Apartment in City Centre

$203 nightly
The price is $234
Dec 15 - Dec 16
Total with taxes and fees
Clean and spacious 3BR DT Windsor Laundry and parking
Interior
Windsor Perfect Stay

Apartment in Remington Park

$95 nightly
The price is $107
Dec 30 - Dec 31
Total with taxes and fees
Windsor Perfect Stay
Fridge, microwave, oven, stovetop
Cheerful Family Home 3 mins drive to UWindsor

Vacation Home in Bridgeview

$237 nightly
The price is $274
Jan 7 - Jan 8, 2026
Total with taxes and fees
Cheerful Family Home 3 mins drive to UWindsor
Dining
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !

Vacation Home in Walkerville

10.0 out of 10, Exceptional, (3)
"Loved the atmosphere of the place. Would highly recommend of you're wanting something nice that's close to the casino. I would definitely book again "
United States
Keith S.
$289 nightly
The price is $326
Dec 12 - Dec 13
Total with taxes and fees
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Exterior
Cozy place

Apartment in Walkerville

$127 nightly
The price is $144
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy place
Exterior
Stylish 2bd DT Laundry and Parking

Apartment in City Centre

$163 nightly
The price is $188
Dec 14 - Dec 15
Total with taxes and fees
Stylish 2bd DT Laundry and Parking
Interior
Penthouse suite in heart of little Italy

Apartment in Walkerville

8.2 out of 10, Very Good, (11)
"Lovely little place. Especially enjoyed the deck out back. Tough getting in and out on that tiny, steep stair in the back, and parking was kind of a monster. Made it, but unfortunately that was the biggest memory of the stay for my kids - the stairs."
United States
Israel J.
$248 nightly
The price is $280
Dec 15 - Dec 16
Total with taxes and fees
Penthouse suite in heart of little Italy
Outdoor pool, a heated pool
Luxury getaway with pool and hot tub - family retreat

Vacation Home in Roseland

8.0 out of 10, Very Good, (3)
"Clean and gorgeous backyard with heated pool and jacuzzi"
United States
Mohammed M.
$438 nightly
The price is $494
Dec 12 - Dec 13
Total with taxes and fees
Luxury getaway with pool and hot tub - family retreat
Exterior
7BR house 19 ppl DT Windsor Free Parking

Vacation Home in City Centre

4.0 out of 10, (1)
"The main floor refrigerator didn’t work and the roof leaked when it rained all over the master bed through the ceiling fan."
United States
Mark D.
$490 nightly
The price is $566
Jan 8 - Jan 9, 2026
Total with taxes and fees
7BR house 19 ppl DT Windsor Free Parking
Exterior
Quaint Clean 2BR DT Windsor Laundry and parking Inc

Apartment in City Centre

2.0 out of 10, (1)
"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.
$164 nightly
The price is $190
Dec 29 - Dec 30
Total with taxes and fees
Quaint Clean 2BR DT Windsor Laundry and parking Inc
Fridge, microwave, oven, stovetop
Little Belle River home

Vacation Home in Belle River

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice, cozy spot. Very clean, all required amenities and a very responsive host "
United States
Matthew S.
$92 nightly
The price is $104
Jan 8 - Jan 9, 2026
Total with taxes and fees
Little Belle River home
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

Stonecroft Inn

Stonecroft Inn

10/10 Excellent
"Great and helpful staff "
Deirdre 1-night trip
Posted 6 hours ago
Stonecroft Inn

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 $117 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?

Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests: Visitors give good reviews to this Windsor vacation home rental, which is located on a lake and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind. Some other homes for rent in Windsor include Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border and Cozy comfort lower level unit.

How many vacation rentals will I find in Windsor?

With 92 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 Dieppe Gardens, whereas Windsor Riverfront and Lake Saint Clair are a couple of great spots to enjoy the outdoors. Detroit Windsor Tunnel and Chrysler Theatre are other places to visit while you're in town.

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.