Windsor Holiday Rentals

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Holiday Rentals in Windsor

Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests

Walkerville
9.0 out of 10, Wonderful, (11)
"We were attending a wedding in Detroit and decided to stay in Windsor. The little house was perfect for my husband, myself and our two daughters. A Timmy's is within walking distance. "
United States
Christina P.
The price is NZ$384
includes taxes & fees
11 Nov - 12 Nov
Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests

Cozy comfort lower level unit

Roseland
9.8 out of 10, Exceptional, (8)
"Spent time here for work and it was very convenient for me. "
Canada
Geoff T.
The price is NZ$205
includes taxes & fees
10 Nov - 11 Nov
Cozy comfort lower level unit

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

Roseland
8.4 out of 10, Very good, (6)
"Very nice unit. Prisca is a fantastic host. Great communications. I highly recommend this property!"
United States
Thomas M.
The price is NZ$540
includes taxes & fees
10 Nov - 11 Nov
Modern Spacious 1 bedroom and a den home (Lower Unit)

Windsor Manor

4.0 star property
City Centre
The price is NZ$521
includes taxes & fees
10 Dec - 11 Dec
Windsor Manor

Penthouse suite in heart of little Italy

Walkerville
8.0 out of 10, Very good, (10)
"Kevin was very thoughtful and checked on us throughout our stay as well as before and after. The place is more beautiful than the photos and was clean! It is in an amazing location right by the downtown area. Check in and check out was easy, no complaints! Will have to come back!"
United States
grace e.
The price is NZ$491
includes taxes & fees
10 Nov - 11 Nov
Penthouse suite in heart of little Italy

The Hipster House

Walkerville
9.6 out of 10, Exceptional, (23)
"We were guests for 2 nights in Detroit for Concerts at Ford Field and couldn't have asked for better accommodations. Minutes to a parking area once clear of the tunnel and Customs on the USA side. Lottsa space to flake out, play cards, and Sunday Sports! Nice Kitchen to cook all our meals and stoke up for our concerts! Thanks Anthony and Jaqueline!!"
Canada
Nathan T.
The Hipster House

Min to DT/USA - Luxurious House - 4bed-2bath

Bridgeview
9.6 out of 10, Exceptional, (8)
"Great property for family visit. Very clean and comfortable "
Canada
Cathy B.
Min to DT/USA - Luxurious House - 4bed-2bath

GLOBALSTAY. Unique New Townhomes for 16 Guests. HOT TUB, BBQ

4.5 star property
Walkerville
7.4 out of 10, Good, (11)
"Excellent Accommodations highly recommended."
Canada
michael
GLOBALSTAY. Unique New Townhomes for 16 Guests. HOT TUB, BBQ

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

Devonshire
8.8 out of 10, Excellent, (5)
"I booked the place several months prior to my arrival. I was traveling with friends from MD to Windsor to participate in a bike ride. Since this was my first time booking a place via VRBO, I was nervous about not having access. I asked for the info and was told I would get it the day of our arrival. She informed me it was typically provided 30 minutes prior to check-in.I received it an hour or so prior to check-in. Once I got the info and arrived on site, the place was great. It looked as...
United States
Roger M.
The price is NZ$248
includes taxes & fees
28 Nov - 29 Nov
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

The Victorian on Victoria

Downtown Windsor
9.0 out of 10, Wonderful, (16)
"We thoroughly enjoyed our stay at the Victorian. We liked the cleanliness, amenities, cool back yard and close location to many restaurants. Our hosts were very available for any questions or concerns that we may have had. Strongly recommend!"
Canada
Janette S.
The Victorian on Victoria

Access to the beach and riverside trail.

Sandwich
9.8 out of 10, Exceptional, (11)
"We had a great stay at this property. It’s in such a great location right at the start of the Windsor Sculpture Park and Riverfront Trail. We brought our bicycles and had some great rides along the river. The property itself was very clean, safe, quiet and has everything we needed. The bed was comfy and the shower had great pressure/temperature. We will definitely stay here again next time we are in Windsor."
United States
laurie p.
Access to the beach and riverside trail.

Centrally located 3BDRM home in CityCore!

Downtown Windsor
Centrally located 3BDRM home in CityCore!

Three Bedroom Three Bath Penthouse with Sauna & Exercise/Office Space

Bridgeview
9.0 out of 10, Wonderful, (18)
"Spacious."
United States
Maureen Bridget S.
Three Bedroom Three Bath Penthouse with Sauna & Exercise/Office Space

Cozy 2 Bdrm, Lounge w/fpl, Kitchenette, TV, Wi-Fi

East Riverside
9.4 out of 10, Exceptional, (3)
"Totally accurate pictures and description, wonderful area, walking biking jogging. Well located yet very quiet and I will return there for sure."
Canada
Rochelle B.
The price is NZ$363
includes taxes & fees
10 Nov - 11 Nov
Cozy 2 Bdrm, Lounge w/fpl, Kitchenette, TV, Wi-Fi

Luxury getaway with pool and hot tub - family retreat

Roseland
8.0 out of 10, Very good, (3)
"The place itself is nice, but if you're going to rent this beware, you share the pool in the backyard with the people she rents out to downstairs, which is not listed on the first page. It's listed under the 60th amenity. You are also being watch twenty 47.They don't take the eyes off their cameras"
Canada
Brenda L.
The price is NZ$935
includes taxes & fees
19 Nov - 20 Nov
Luxury getaway with pool and hot tub - family retreat

Waterfront Retreat: 6BR Home, BBQ, Sleeps 10

East Riverside
9.6 out of 10, Exceptional, (4)
"Lovely place to stay with the family for an extended period!"
United States
Andrew C. T.
Waterfront Retreat: 6BR Home, BBQ, Sleeps 10

Luxurious and Fashionable Home | Sleeps 8

Walkerville
9.8 out of 10, Exceptional, (16)
"Wonderful stay. Spacious clean property "
United States
James S.
Luxurious and Fashionable Home | Sleeps 8

Residence & Conference Centre - Windsor

2.0 star property
Roseland
8.2 out of 10, Very good, (400)
"Would definitely return to the Residence & Conference Centre in the future! "
Canada
Sara
Residence & Conference Centre - Windsor

Cozy place

Walkerville
The price is NZ$252
includes taxes & fees
1 Dec - 2 Dec
Cozy place

7BR house 19 ppl DT Windsor Free Parking

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.
The price is NZ$1,004
includes taxes & fees
30 Nov - 1 Dec
7BR house 19 ppl DT Windsor Free Parking
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$205 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 holiday 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 holiday.

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 holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Adventure Bay Family Water Park, or you can select a more secluded option if you're looking for 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 holiday rentals that Windsor has to offer?

Steps to Caesars, Riverfront & Dining! Hot Tub Add-On, Sleeps 9 Guests: This highly rated holiday home rental in Windsor 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 that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Some other homes for rent in Windsor include Cozy comfort lower level unit and Modern Spacious 1 bedroom and a den home (Lower Unit).

How many holiday rentals will I find in Windsor?

With 92 Expedia holiday rentals, you're guaranteed 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 Coventry Gardens are a couple of great spots to enjoy the outdoors. You’ll find favourite places to visit such as MGM Grand Detroit Casino and Comerica Park in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.