Windsor vacation rentals
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Top-rated vacation rentals in Windsor
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor vacation rentals
Windsor house rentals
Home in Detroit
4.9 out of 5 average rating, 42 reviewsOhana House
Home in The Core
4.82 out of 5 average rating, 107 reviews3 Bed Bright Modern Home in Heart of Walkerville
Home in Windsor
4.97 out of 5 average rating, 182 reviewsShalom - Modern Spacious Home, 4BR + 3BA
Home in Windsor
4.89 out of 5 average rating, 209 reviewsStunning Top Tier Modern Home Is Ready To Host You
Home in Amherstburg
4.9 out of 5 average rating, 101 reviewsThat place by the Lake
Home in Windsor
5 out of 5 average rating, 8 reviewsBlue Heron Home
Home in Windsor
4.87 out of 5 average rating, 38 reviewsFull house, 3 BDR, 2WR, free Parking , extra beds
Home in Harper Woods
4.87 out of 5 average rating, 109 reviewsElegant & spacious 3/2 Gem in Harper Woods
Other great vacation rentals in Windsor
Bungalow in Amherstburg
4.96 out of 5 average rating, 24 reviewsAmazing Space w/ Kitchen, near waterfront area
Home in Amherstburg
4.97 out of 5 average rating, 72 reviewsErie View Lakehouse - Serene and Spacious
Cottage in Leamington
4.98 out of 5 average rating, 40 reviewsSunsets by the Bay - Your Waterfront Oasis
Townhouse in Windsor
5 out of 5 average rating, 16 reviewsExecutive Home Rental, Sleeps 7
Loft in Wyandotte
5 out of 5 average rating, 3 reviewsLoft, Open Concept, Balcony 2 Bed, Pool Gym, Wifi
Rental unit in Grosse Pointe Park
4.85 out of 5 average rating, 13 reviewsVilla del Lago Grosse Pointe Park King w/ 2 Queens
Home in Amherstburg
4.81 out of 5 average rating, 69 reviewsEnjoy the best view in town!
Cottage in Belle River
5 out of 5 average rating, 39 reviewsUrban Cottage Adorable Shabby Chic Getaway for 2
Quick stats about vacation rentals in Windsor
Total rentals
1.5K properties
Total number of reviews
69K reviews
Family-friendly rentals
600 properties are a good fit for families
Pet-friendly rentals
380 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
860 properties have a dedicated workspace
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 vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 860 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 380 vacation rentals for guests traveling with pets.
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