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Top Holiday Rentals in Windsor

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

8.0 out of 10, Very good, (2)
"This house was beautiful and spotless — a brand-new 2-bedroom, 2-bathroom home with lots of storage and even a basement space if needed. The kitchen was fully equipped with dishes, cookware, and even some condiments, while the bathrooms had toiletries and extra toothbrushes — such thoughtful touches! The décor was simple, classy, and inviting, right down to the elegant cups and glasses. The open-concept design made the space feel bright and welcoming, perfect for families or two couples to relax...
The price is £120
includes taxes & fees
6 Jul - 7 Jul
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border

Enjoy the Hot Tub while staying close to Caesars, Riverfront, Downtown & Dining!

8.8 out of 10, Excellent, (9)
"It was easy and simple process to check in and check out. House was very clean, updated and spacious."
The price is £170
includes taxes & fees
9 Jul - 10 Jul
Enjoy the Hot Tub while staying close to Caesars, Riverfront, Downtown & Dining!

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

10.0 out of 10, Exceptional, (11)
"Great stay! "
The price is £138
includes taxes & fees
10 Jul - 11 Jul
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

Cozy comfort lower level unit

10.0 out of 10, Exceptional, (7)
"We enjoyed our stay very much."
The price is £89
includes taxes & fees
6 Jul - 7 Jul
Cozy comfort lower level unit

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

7.0 out of 10, Good, (6)
"was a great property and location"
The price is £267
includes taxes & fees
7 Jul - 8 Jul
Modern Spacious 1 bedroom and a den home (Lower Unit)

Perfect hideaway with a hot tub and a fireplace

10.0 out of 10, Exceptional, (11)
"My wife and I came for a valentine day night and we were more than thrilled. Everything was terrific! "
The price is £213
includes taxes & fees
7 Jul - 8 Jul
Perfect hideaway with a hot tub and a fireplace

Fully Furnished 2 bedroom house in Windsor

The price is £115
includes taxes & fees
13 Jul - 14 Jul
Fully Furnished 2 bedroom house in Windsor

Cheerful Family Home 3 mins drive to UWindsor

The price is £239
includes taxes & fees
13 Jul - 14 Jul
Cheerful Family Home 3 mins drive to UWindsor

Perfect 3 bedroom house in prime location of South Windsor. max 6 guests

8.0 out of 10, Very good, (1)
The price is £173
includes taxes & fees
6 Jul - 7 Jul
Perfect 3 bedroom house in prime location of South Windsor. max 6 guests

Modern 3BR Walkerville Unit | Near Downtown

The price is £215
includes taxes & fees
6 Jul - 7 Jul
Modern 3BR Walkerville Unit | Near Downtown

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

10.0 out of 10, Exceptional, (1)
"This place spared no detail. Huge compliments to the hosts, who have an insanely adept eye for design. Perfectly well equipped, comfortable beds, well stocked kitchen… Loved everything about it, will stay no one where else when traveling through Windsor again. Thank you!! "
The price is £189
includes taxes & fees
7 Jul - 8 Jul
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !

Windsor Retreat • Fire Pit • Huge Yard • Sleeps 10

The price is £313
includes taxes & fees
7 Jul - 8 Jul
Windsor Retreat • Fire Pit • Huge Yard • Sleeps 10

7BR house 19 ppl DT Windsor Free Parking

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."
The price is £486
includes taxes & fees
7 Jul - 8 Jul
7BR house 19 ppl DT Windsor Free Parking

Luxury getaway with pool and hot tub - family retreat

8.0 out of 10, Very good, (3)
"Clean and gorgeous backyard with heated pool and jacuzzi"
The price is £725
includes taxes & fees
6 Jul - 7 Jul
Luxury getaway with pool and hot tub - family retreat

Hidden Gem-Charming 2-bedroom house with WiFi and AC in welcoming Saint Joachim

The price is £222
includes taxes & fees
13 Jul - 14 Jul
Hidden Gem-Charming 2-bedroom house with WiFi and AC in welcoming Saint Joachim

Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville

9.8 out of 10, Exceptional, (7)
"Great Lake property getaway in a beautiful area. Lots of restaurants and breweries within 10 minutes."
The price is £184
includes taxes & fees
8 Jul - 9 Jul
Reveries on the Lake-lakefront Kingsville Cottage, Your home away from home in Kingsville

Beachfront 5BDRM Lakehouse

2.0 out of 10, (1)
The price is £462
includes taxes & fees
7 Jul - 8 Jul
Beachfront 5BDRM Lakehouse

Queen & Mill - Family Fun steps to downtown, parks, spa, and 3km to golf course

10.0 out of 10, Exceptional, (18)
"The property is within walking distance of downtown, very clean, and features comfy beds. The host is quick to respond and they provided extra amenities, a welcome bottle of wine and Brita water in the fridge. The decor and fixtures are stylish, and there's plenty of space."
The price is £277
includes taxes & fees
6 Jul - 7 Jul
Queen & Mill - Family Fun steps to downtown, parks, spa, and 3km to golf course

The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca

9.8 out of 10, Exceptional, (49)
"We enjoyed our stay at the Cedar house. It was clean and comfortable. I would recommend it to anyone. "
The price is £224
includes taxes & fees
11 Jul - 12 Jul
The Cedar House. Minutes from the lake, wineries and golf. www.thecedarhouse.ca

Wild Goose Landing- Located near local wineries and breweries

10.0 out of 10, Exceptional, (20)
"Great place, clean, modern, beautiful natural view of the back yard, really enjoyed our stay, strongly recommend "
The price is £219
includes taxes & fees
10 Jul - 11 Jul
Wild Goose Landing- Located near local wineries and breweries
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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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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best holiday rentals that Windsor has to offer?

Enjoy the Hot Tub while staying close to Caesars, Riverfront, Downtown & Dining!: 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 Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor. and Cozy comfort lower level unit.

How many holiday rentals will I find in Windsor?

With 85 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 Lake Saint Clair are a couple of great spots to enjoy the outdoors. You’ll find favourite places to visit such as MGM Grand Detroit Casino and Ford Field 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.