Windsor vacation rentals

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Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Little Caesars Arena159 locals recommend
Comerica Park212 locals recommend
Ford Field164 locals recommend
Caesars Windsor102 locals recommend
Fox Theatre75 locals recommend
Hart Plaza66 locals recommend

Other great vacation rentals in Windsor

Guest favorite

Home in Windsor, Canada

4.97 out of 5 average rating, 158 reviews

Shalom - Modern Spacious Home, 4BR + 3BA

Mar 24 – 31

G$31,982 GYD per night
Guest favorite

Loft in Kingsville, Canada

5.0 out of 5 average rating, 229 reviews

The Hudson Loft

Oct 13 – 20

G$31,081 GYD per night
Superhost

Villa in Windsor, Canada

4.9 out of 5 average rating, 134 reviews

Cheerful 4-bedroom home by the river.

Feb 3 – 10

G$33,766 GYD per night
Guest favorite

Home in Windsor, Canada

4.89 out of 5 average rating, 183 reviews

Stunning Top Tier Modern Home Is Ready To Host You

Oct 20 – 27

G$28,977 GYD per night
Guest favorite

Farm stay in Essex, Canada

5.0 out of 5 average rating, 135 reviews

Luxury Farm Stay - Hot tub - Allow pets - Firepits

Oct 26 – Nov 2

G$52,484 GYD per night
Superhost

Barn in Essex, Canada

4.91 out of 5 average rating, 336 reviews

14th Homestead Barn Loft

Mar 7 – 14

G$31,296 GYD per night
Guest favorite

Guest suite in Windsor, Canada

4.92 out of 5 average rating, 105 reviews

Covid Clean 2 bdrm Entire Lower Level Sport Themed

Oct 3 – 10

G$12,776 GYD per night
Guest favorite

Cottage in Kingsville, Canada

4.9 out of 5 average rating, 191 reviews

Lakeview Inn

Apr 15 – 22

G$33,052 GYD per night

Other great vacation rentals in Windsor

Guest favorite

Home in Hazel Park, Michigan, US

4.98 out of 5 average rating, 185 reviews

The Little Hamster - Near Ferndale & RO w/ 2TVs

May 7 – 14

G$28,825 GYD per night
Guest favorite

Cottage in Essex

4.94 out of 5 average rating, 104 reviews

The Hideaway

Sep 21 – 26

G$27,877 GYD per night
Guest favorite

Cottage in Lakeshore, Canada

5.0 out of 5 average rating, 116 reviews

Beau Chalet de Pointe-aux-Roches (No Cleaning Fee)

Oct 1 – 8

G$33,411 GYD per night
Guest favorite

Home in Kingsville

4.99 out of 5 average rating, 182 reviews

La Perla - Lakefront Retreat in Wine Country!

Sep 29 – Oct 6

G$46,415 GYD per night
Guest favorite

Home in Windsor, Canada

4.97 out of 5 average rating, 35 reviews

Executive One-Bedroom Upper Unit

Jan 1 – 8

G$17,774 GYD per night
Guest favorite

Home in Windsor, Canada

5.0 out of 5 average rating, 27 reviews

The Spot - Luxury Living

Jan 23 – 30

G$15,380 GYD per night
Guest favorite

Apartment in Windsor

5.0 out of 5 average rating, 26 reviews

Stylish luxury apartment

Nov 15 – 22

G$16,571 GYD per night
Guest favorite

Home in Windsor

5.0 out of 5 average rating, 31 reviews

Perfect hideaway with a hot tub and a fireplace

Sep 24 – Oct 1

G$31,545 GYD per night

Quick stats about vacation rentals in Windsor

  • Total rentals

    1.4K properties

  • Rentals with dedicated workspaces

    830 properties have a dedicated workspace

  • Rentals with a pool

    110 properties have a pool

  • Pet-friendly rentals

    350 properties allow pets

  • Family-friendly rentals

    570 properties are a good fit for families

  • Total number of reviews

    65K reviews

Frequently Asked Questions

  • How is the weather in Windsor?

    Windsor has a humid continental climate with four distinct seasons. Summers can be hot, reaching up to 86°F (30°C), while winters are cold with temperatures dropping to around 20°F (-6°C). Snowfall is common in winter, which makes for great winter sports activities.

  • What are some of the best things to do in Windsor?

    In Windsor, you can explore the unique outdoor art at Windsor Sculpture Park, tour the historic Willistead Manor, or enjoy a day of fun at the Adventure Bay Family Water Park. Nature lovers also enjoy hiking the trails in Devonwood Conservation Area.

  • What is the best time of year to visit Windsor?

    The most popular time to visit Windsor is during the summer months from June to August. This is when you can enjoy the Windsor Summer Fest, an annual festival with carnival rides, concerts, and fireworks. The warm weather also allows for exploration of the city's outdoor attractions.

  • What are the best places to stay in Windsor?

    Downtown Windsor is a popular area to stay due to its easy access to restaurants, shops, and attractions like the Art Gallery of Windsor. Walkerville, known for its historic charm, and Riverside, with its waterfront views, are also frequently suggested.

  • What are the best places to visit in Windsor?

    Visitors often enjoy exploring the Windsor Sculpture Park, filled with quirky outdoor art, or touring the historic Willistead Manor. The Adventure Bay Family Water Park is also a frequent favorite, especially for those traveling with children.

  • What are some hiking trails in Windsor?

    Windsor is home to several hiking trails. The Ganatchio Trail, running along the Detroit River, is perfect for waterfront views, while the Little River Extension offers winding paths through lush greenery. For a forested hike, try the Devonwood Conservation Area.

  • What are some family activities to do in Windsor?

    Take the family for a fun-filled day at the Adventure Bay Family Water Park, or explore the exhibits at the Windsor Science Centre. For a more relaxed day, pack a picnic and head to the Peche Island, a 100-acre island with trails, wildlife, and picnic spots.

  • What are some of the best day trip ideas in Windsor?

    You could take a day trip to Point Pelee National Park, an excellent destination for bird watching and hiking, located just 60 minutes (60 miles/97 km) away. Alternatively, visit the Detroit Science Centre, a quick 10 minutes (3 miles/5 km) trip across the Detroit River.

  • Are there pet-friendly vacation rentals in Windsor?

    Four-legged friends are welcome in Windsor. Choose from more than 350 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Windsor?

    Yes! Work meets play with ease at over 830 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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  3. Ontario
  4. Essex County
  5. Windsor