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Windsor Vacation Rentals

Find 631 available home rentals from 9 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Windsor

Find your perfect vacation rental in Windsor from just $74 per night!

House Windsor
-11%
Jul 5 - Jul 12
House ∙ 5 guests ∙ 2 bedrooms

House

Windsor, Essex County, Canada
$267$237
per night
$267$237
per night
View deal
House Windsor
-17%
Aug 2 - Aug 9
House ∙ 4 guests ∙ 2 bedrooms

House

Windsor, Essex County, Canada
$199$163
per night
Outstanding(4 ratings)
$199$163
per night
View deal
House Windsor
-12%
Aug 2 - Aug 9
House ∙ 2 guests ∙ 1 bedroom

House

Windsor, Essex County, Canada
$270$238
per night
Outstanding(15 ratings)
$270$238
per night
View deal
House Windsor
-8%
Aug 2 - Aug 9
House ∙ 10 guests ∙ 4 bedrooms

557 m² House

Windsor, Essex County, Canada
$1,032$968
per night
Very good(6 ratings)
$1,032$968
per night
View deal
House Windsor
-16%
Jul 5 - Jul 12
House ∙ 6 guests ∙ 3 bedrooms

House

Windsor, Essex County, Canada
$587$493
per night
$587$493
per night
View deal
House Windsor
-12%
Jun 21 - Jun 28
House ∙ 5 guests ∙ 3 bedrooms

House

Windsor, Essex County, Canada
$159$139
per night
Excellent(7 ratings)
$159$139
per night
View deal
Apartment Windsor
Aug 2 - Aug 9
Apartment ∙ 7 guests ∙ 4 bedrooms

150 m² Apartment

Windsor, Essex County, Canada
$281
per night
$281
per night
View deal
House Windsor
-17%
Jul 19 - Jul 26
House ∙ 5 guests ∙ 2 bedrooms

House

Windsor, Essex County, Canada
$229$196
per night
$229$196
per night
View deal
Condo Windsor
Aug 9 - Aug 16
Condo ∙ 2 guests ∙ 1 bedroom

102 m² Condo

Windsor, Essex County, Canada
$137
per night
Outstanding(5 ratings)
$137
per night
View deal
House Windsor
Aug 2 - Aug 9
House ∙ 6 guests ∙ 3 bedrooms

House

Windsor, Essex County, Canada
$211
per night
Excellent(43 ratings)
$211
per night
View deal
House Windsor
Mar 22 - Mar 29
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

Windsor, Essex County, Canada
$231
per night
Outstanding(2 ratings)
$231
per night
View deal
House Windsor
-8%
Mar 22 - Mar 29
House ∙ 4 guests ∙ 2 bedrooms

House

Windsor, Essex County, Canada
$413$374
per night
Outstanding(1 rating)
$413$374
per night
View deal
House Windsor
-8%
Aug 2 - Aug 9
House ∙ 8 guests ∙ 4 bedrooms

House

Windsor, Essex County, Canada
$513$473
per night
Outstanding(3 ratings)
$513$473
per night
View deal
Apartment Windsor
Apr 26 - May 3
Free cancellation
Apartment ∙ 5 guests ∙ 2 bedrooms

62 m² Apartment

Windsor, Essex County, Canada
$170
per night
$170
per night
View deal
Motel Windsor
Mar 22 - Mar 29
Free cancellation
Motel ∙ 2 guests ∙ 1 bedroom

Kenora Motel

Windsor, Essex County, Canada
$107
per night
Very good
$107
per night
View deal

Vacation rentals and apartments with air conditioning

House  Windsor
Jul 26 - Aug 2
$108 per night
2 guests ∙ 1 bedroom

House

Windsor, Essex County, Canada
Air conditioning
View deal
House  Windsor
Jul 20 - Jul 27
-11%
$326
$291 per night
House ∙ 10 guests ∙ 5 bedrooms

204 m² House

5.0
Outstanding(4 ratings)
Windsor, Essex County, Canada
Air conditioning
View deal
House  Windsor
Apr 9 - Apr 16
-8%
$86
$80 per night
2 guests ∙ 1 bedroom

House

Windsor, Essex County, Canada
Air conditioning
View deal
See all offers

Best vacation rentals with a balcony

Apartment  Windsor
Jul 26 - Aug 2
$219 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

150 m² Apartment

Windsor, Essex County, Canada
Balcony
View deal
House  Windsor
Jul 26 - Aug 2
-23%
$295
$227 per night
House ∙ 5 guests ∙ 2 bedrooms

102 m² House

Windsor, Essex County, Canada
Balcony
View deal
House  Windsor
Apr 9 - Apr 16
-8%
$330
$302 per night
10 guests ∙ 4 bedrooms

House

4.9
Outstanding(26 ratings)
Windsor, Essex County, Canada
Balcony
View deal
See all offers

Vacation rentals with a fireplace

Motel  Windsor
Mar 29 - Apr 5
$105 per night
Motel ∙ 4 guests ∙ 1 bedroom

Standard Room, 2 Double Beds, Non Smoking

Windsor, Essex County, Canada
Fireplace
View deal
Motel  Windsor
Mar 29 - Apr 5
$95 per night
Motel ∙ 2 guests ∙ 1 bedroom

Standard Room, 1 Queen Bed, Non Smoking

Windsor, Essex County, Canada
Fireplace
View deal
House  Windsor
Jul 26 - Aug 2
-4%
$512
$493 per night
7 guests ∙ 3 bedrooms

House

4.6
Excellent(10 ratings)
Windsor, Essex County, Canada
Fireplace
View deal
See all offers

Best Vacation Home Deals in Windsor

Save up to 17%

House Windsor
Mar 29 - Apr 5
-3%
$232
$226 per night
House ∙ 6 guests ∙ 2 bedrooms

139 m² House

4.1
Very good(6 ratings)
Windsor, Essex County, Canada
View deal
House Windsor
Jul 26 - Aug 2
-11%
$341
$303 per night
3 guests ∙ 1 bedroom

House

Windsor, Essex County, Canada
View deal
House Windsor
Jul 26 - Aug 2
-17%
$205
$171 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Windsor, Essex County, Canada
View deal

631 fantastic vacation rentals from 9 vacation rental websites are available in Windsor, with prices beginning at $74 per night. Using HomeToGo's search feature you can instantaneously search and compare the offers of each listed rental to discover the best deal and save up to 17%.

Budget-friendly Rentals in Windsor

Find Fantastic yet Inexpensive Rentals

House Windsor
Jul 27 - Aug 3
$232 per night
2 guests ∙ 2 bedrooms

House

Windsor, Essex County, Canada
Free cancellation
View deal
Condo Windsor
Jun 28 - Jul 5
-8%
$236
$218 per night
4 guests ∙ 2 bedrooms

Condo

5.0
Outstanding(10 ratings)
Windsor, Essex County, Canada
View deal
House Windsor
from $173 per night
2 guests ∙ 2 bedrooms

House

5.0
Outstanding(7 ratings)
Windsor, Essex County, Canada
View deal

Top-Rated Offers and Accommodations in Windsor

Book Vacation Rentals with the Highest User Rating

House Windsor
Dec 14 - Dec 21
$364 per night
House ∙ 6 guests ∙ 3 bedrooms

112 m² House

4.6
Excellent(27 ratings)
Windsor, Essex County, Canada
View deal
House Windsor
Dec 14 - Dec 21
-47%
$453
$250 per night
House ∙ 4 guests ∙ 2 bedrooms

97 m² House

4.5
Excellent(2 ratings)
Windsor, Essex County, Canada
View deal
House Windsor
Dec 14 - Dec 21
-32%
$821
$378 per night
House ∙ 6 guests ∙ 3 bedrooms

167 m² House

5.0
Outstanding(1 rating)
Windsor, Essex County, Canada
View deal

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Windsor

  • WiFi (605)
  • Pet-friendly (157)
  • Pool (185)
  • Kitchen (238)
  • Parking (30)
  • Washing machine (238)
  • Air conditioning (601)
  • TV (517)
  • Dishwasher (73)
  • Balcony/patio (80)
  • Grill (123)
  • Yard (105)

Windsor is a fantastic vacation destination if you want a property with a pool, as 27% of the vacation rentals there have one. Additionally, more House rental have pools than any other accommodation type. They are a great choice if you go in a group of 9, as that is the number of people they can usually accommodate. You can also find and book a vacation home providing a pool near the water, which is the case for many of the rentals in this destination.

Dip into a Vibrant Cultural Life with Windsor Accommodation

Windsor is a city with both a geographical quirk - it's almost the only place on the border where you go south to enter Canada - and historical infamy. It was once a source for liquor smuggled over the border during prohibition. Today, it offers visitors plenty to see and do while its rich diversity promotes a vibrant gastronomic scene. For your Windsor stay, select short term rental accommodation that ranges from city apartments and historic houses to rustic rural cottages.

What are the best places to discover the arts and culture of Windsor?

Windsor's Art and Cultural scene

If the sun is shining, visit Windsor Sculpture Park with its 35 huge exhibits.

Alternatively, if the weather isn't so good, spend a couple of hours at the Art Gallery of Windsor.

This long-established venue has one of the country's best displays of Canadian art.

What are the must-see attractions in Windsor?

While Away the Hours in Windsor

Explore Windsor's History

A historic site close to any Windsor accommodation is Willistead Manor, designed in the Tudor-Jacobean style by Albert Kahn. Inside are many rooms to explore while its beautiful grounds play host to Arts in the Park every June. François Bâby House is now home to Windsor's Community Museum while the Sandwich First Baptist Church was established by successful users of the Underground Railroad.

Ojibwe Prairie Complex

Plan a day out from your short term rental with a visit to the Ojibway Prairie Complex. Hike or cycle through its different nature reserves before learning about its history, flora and fauna in the Educational Centre. Keep an eye out for a huge variety of birds as well as lizards, frogs, turtles, snakes and, in the evening, bats.

Roy A. Battagello River Walk Bike Trail

Enjoy a few hours on the eight-kilometre long Roy A. Battagello River Walk Bike Trail. It winds its way from Ambassador Bridge through Downtown Windsor to Dieppe Gardens and the Windsor Sculpture Park. Take time out to enjoy the views or tuck into a picnic prepared in your Windsor accommodation.

Adventure Bay Family Water Park

Close to your Windsor accommodation is Adventure Bay Family Water Park, perfect for family fun. It features five waterslides from the toddler-friendly Tot Loch to the thrilling Python along with a wave pool, lazy river, surf simulator and giant adventure playground.

Sandpoint Beach

Sandpoint Beach will be close to your Windsor accommodation wherever you choose to stay. Spend a lazy day swimming and sunbathing or take to the water for paddle boarding and windsurfing.

Information about vacation rentals in Windsor

🏡 Vacation rentals available 631 rentals
💳 Possible discounts up to 17%
🌙 Nightly prices starting at $74
⭐ Popular amenities Internet, Pets allowed and Pool
🐾 Pet friendly homes 154 homes
🏊 Vacation rentals with pools 173 homes
230,222 reviews
Windsor vacation rentals have an average rating of 4/5 on 230,222 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Windsor?

At the moment, there are 631 vacation homes from 9 different providers in Windsor.

What are the most popular vacation home amenities in Windsor?

When looking to book a vacation home in Windsor, the most requested amenities include Internet, Pets allowed, and Pool.

Are there pet-friendly vacation rentals in Windsor?

Yes, there are 154 pet-friendly vacation rentals in Windsor, with an average nightly price of $248.

What's the best month to book a vacation rental in Windsor?

If you're looking for balmy weather, July and August are typically the hottest months in Windsor with temperatures around 27 °C. January and February in Windsor are the coldest, with -8 °C on average.

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