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
Other great vacation rentals in Windsor
Barn in Essex
4.91 out of 5 average rating, 335 reviews14th Homestead Barn Loft
Jan 7 – 14
Home in Kingsville
4.99 out of 5 average rating, 181 reviewsLa Perla - Lakefront Retreat in Wine Country!
Oct 30 – Nov 6
Loft in Kingsville
5.0 out of 5 average rating, 228 reviewsThe Hudson Loft
Aug 2 – 9
Apartment in Windsor
4.95 out of 5 average rating, 55 reviewsThe Boho Oasis: Studio Apartment
Oct 3 – 10
Home in Windsor
4.97 out of 5 average rating, 32 reviewsExecutive One-Bedroom Upper Unit
Feb 9 – 16
Home in Windsor
4.97 out of 5 average rating, 32 reviewsBoutique Suite on the River
Jun 3 – 8
Apartment in Windsor
5.0 out of 5 average rating, 20 reviewsStylish luxury apartment
Sep 25 – Oct 2
Home in Windsor
5.0 out of 5 average rating, 30 reviewsPerfect hideaway with a hot tub and a fireplace
Dec 6 – 13
Other great vacation rentals in Windsor
Townhouse in Windsor
4.93 out of 5 average rating, 46 reviewsThe Chilver Place
Nov 28 – Dec 5
Home in Windsor
5.0 out of 5 average rating, 14 reviewsCozy home with parking - near Met Hospital
Jul 1 – 8
Home in Windsor
4.96 out of 5 average rating, 28 reviewsCozy, Modern 2BR w/ Remote Workspace, Patio & Gym
Mar 7 – 14
Apartment in Windsor
4.82 out of 5 average rating, 22 reviewsCharming & Cozy 2BR Unit in the heart of Windsor
Apr 29 – May 6
Guest suite in Amherstburg
4.96 out of 5 average rating, 74 reviewsStylish Private Guest Suite
Sep 9 – 16
Home in Windsor
5.0 out of 5 average rating, 36 reviewsLuxurious 3BR, King Bed, Ensuite. Perfect Stay!
Jan 26 – Feb 2
Apartment in Windsor
4.78 out of 5 average rating, 40 reviewsAffordable Urban Bachelor
Jan 5 – 12
Farm stay in Essex County
5.0 out of 5 average rating, 82 reviewsThe Fir&Feather Tree Farm 1Bedroom Suite & Hot tub
Dec 3 – 10
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.
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