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Vacation rentals in Windsor

Book unique vacation rentals, houses, and more on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor vacation rentals

Self check-in
Monthly stays
Pet friendly
Laptop-friendly workspace
Gym

Stay near Windsor's top sights

Little Caesars Arena140 locals recommend
Ford Field124 locals recommend
Detroit Institute of Arts200 locals recommend
Eastern Market72 locals recommend
Campus Martius Park District132 locals recommend
Motown Museum139 locals recommend

House rentals in Windsor

Top guest favorite
Home in Devonshire
5 out of 5 average rating, 8 reviews

Modern & Cozy Home Retreat

Guest favorite
An open living area is featured, showcasing a dining table with black chairs and a modern design. A corner sectional sofa and large wall-mounted TV are visible. Light-colored walls and a wood-like floor create a seamless flow between the spaces.
Home in Windsor
4.87 out of 5 average rating, 133 reviews

Beautiful 3Bedroom 2Bath Home free parking&laundry

Top guest favorite
A well-maintained putting green is showcased in a spacious backyard, surrounded by lush greenery and decorative string lights illuminating the area. A cozy fire pit area is visible, along with a wooden shed, creating a relaxed outdoor atmosphere ideal for gatherings.
Home in Kingsville
5 out of 5 average rating, 100 reviews

Stylish Getaway steps to DT Kingsville, Spa & Lake

Superhost
A cozy living room is presented, featuring a modern leather sofa and a minimalist coffee table on a natural fiber rug. A floor lamp and potted plant add warmth, while light filters through sheer curtains, enhancing the inviting space.
Home in Walkerville
4.88 out of 5 average rating, 40 reviews

Stylish Apt Near Downtown- Ideal for Long Stays!

Superhost
An outdoor space is defined by a wooden gazebo containing a hot tub, surrounded by greenery from hanging ferns. A small table and adirondack chairs are positioned nearby on a paved area, providing a comfortable spot for relaxation.
Home in Walkerville
4.86 out of 5 average rating, 140 reviews

Hot Tub, TV & Sound bar with fire pit to enjoy.

Superhost
A modern living area features a light gray sectional sofa paired with decorative pillows. A round wooden coffee table is positioned in front, while a wall-mounted TV and shelving with plants add visual interest. Natural light enters through stylish window treatments.
Home in Windsor
4.76 out of 5 average rating, 110 reviews

stylish house in south windsor-2 bedrooms

Guest favorite
An outdoor seating area includes multiple Adirondack chairs arranged around a stone fire pit. A lush lawn leads to a view of the sunset over the water, with string lights hanging from a trellis above. The modern home is visible in the background amid greenery.
Home in Amherstburg
4.96 out of 5 average rating, 112 reviews

The Lake House Ontario

Top guest favorite
A comfortable living room area is shown, featuring a gray sectional sofa and a blue armchair. A round wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Soft lighting enhances the inviting atmosphere.
Home in Belle River
4.94 out of 5 average rating, 63 reviews

little cozy house 2 bedroom

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Dog friendly vacation rentals in Windsor

Guest favorite
Cottage in Essex
4.93 out of 5 average rating, 127 reviews

The Coziest Cottage in Essex County's Wine Country

Guest favorite
A charming cottage is presented with a welcoming front porch and a neatly paved pathway leading to the entrance. Lush greenery and carefully arranged landscaping surround the home, while a tall chimney adds character. Bright blue skies peek through the trees, creating a serene setting.
Cottage in Essex
4.78 out of 5 average rating, 153 reviews

Lakeside getaway

Top guest favorite
A comfortable living area features a leather sofa and patterned armchairs, with a glass coffee table at the center. A ceiling fan hangs above, and the space is illuminated by recessed lighting. An open kitchen with modern appliances is visible in the background.
Apartment in Amherstburg
5 out of 5 average rating, 107 reviews

Navy Yard Flats (Flat A) - Historic Amherstburg

Guest favorite
The upstairs bedroom features two double beds, each dressed in white linens with soft, fur throws draped on top. Light fills the space through large sliding glass doors leading to a balcony, with nature-themed wall art accentuating the neutral decor.
Home in LaSalle
4.86 out of 5 average rating, 154 reviews

Quiet LaSalle Newly Renovated Entire Country Home

Guest favorite
Cottage in Amherstburg
4.91 out of 5 average rating, 149 reviews

Sawiak Waterfront Haven

Guest favorite
A spacious bedroom features a king-size bed with soft linens, placed alongside a decorative fireplace. Natural light enters through two windows, and a green armchair accentuates the space. A colorful area rug and potted plants add warmth and texture to the inviting atmosphere.
Guest suite in Kingsville
4.9 out of 5 average rating, 143 reviews

Main on Main ~ Stylish Studio Downtown Kingsville

Top guest favorite
A unique metal sculpture resembling a bird stands beside a blue adirondack chair on the shoreline. The lake stretches out in the background under a clear blue sky, creating a serene waterfront setting.
Cottage in Leamington
4.99 out of 5 average rating, 308 reviews

It's a 'Shore' thing - Executive Retreat

Guest favorite
A shaded outdoor area features a hot tub under a canopy, surrounded by wooden bar stools. Light beige curtains frame the space, creating a comfortable atmosphere. A wooden table and steps lead to the hot tub, with ample room for relaxation.
Cottage in Essex
4.96 out of 5 average rating, 118 reviews

Chardonnay Bay- June Special! stay 2 get 1 free!

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Dog friendly house rentals Windsor

Top guest favorite
The two-story green house features a generous front porch with seating and is surrounded by a grassy lawn. A detached garage is visible to the right, framed by landscaping. The overall setting is tranquil, with trees lining the background under an overcast sky.
Home in Essex
4.95 out of 5 average rating, 154 reviews

*KID & FAMILY FRIENDLY* Shores of Erie Guest House

Superhost
A bright living area features a sectional sofa adorned with dark blue and neutral cushions. A wooden coffee table sits in front, complemented by a potted plant. A wall-mounted television is present, and a staircase leads to the upper floor, with bookshelves visible in the background.
Home in Windsor
4.73 out of 5 average rating, 26 reviews

Luxury water front 3BR house

Top guest favorite
The exterior of a two-story brick house is visible, featuring a covered front porch with white railings. Windows are adorned with simple treatments, and a small staircase leads to the main entrance. A wooden fence partially encloses the yard, with greenery enhancing the setting.
Home in River Rouge
4.91 out of 5 average rating, 216 reviews

Cozy 1919 House, River Rouge/Detroit.

Top guest favorite
The living room features a bright blue sofa with yellow accent pillows, complemented by a modern area rug. A multi-functional table sits in front of a stylish armchair. A flat-screen TV is mounted on the wall opposite large windows, adorned with golden drapes, allowing natural light.
Home in Dearborn
4.99 out of 5 average rating, 101 reviews

3BD Cozy Chic Home Near *Airport*Beaumont*Downtown

Guest favorite
A tranquil outdoor space is seen with a view of Lake Erie, featuring a wooden deck lined with seating areas. A colorful rug adds interest, while an umbrella offers shade. The Canadian flag stands prominently against the serene backdrop of the water and sky.
Home in Wheatley
4.94 out of 5 average rating, 120 reviews

Erie's Edge lakefront, Point Pelee, Hillman Marsh

Guest favorite
A spacious backyard is surrounded by greenery and trees, featuring a cozy seating area under a gazebo. A fire pit is situated next to a wooden bench, inviting outdoor gatherings. The house's exterior displays a combination of wood and modern finishes, creating an inviting atmosphere.
Home in Spring Garden
5 out of 5 average rating, 58 reviews

Turkey Creek Hideaway

Guest favorite
A grassy shoreline park features a picnic table under a tree, overlooking the lake. The clear blue water is visible in the background, with distant trees and recreational boats creating a peaceful environment.
Home in Frenchtown Charter Township
4.82 out of 5 average rating, 105 reviews

JEN's DEN / Lake Erie Resort/Fishermens Delight!

Guest favorite
A modern bathroom features a spacious deep soaking tub and a walk-in shower with clear glass doors. Sleek gray tiles cover the floor and walls, while a large vanity with storage provides ample space. Soft lighting creates a calming ambiance.
Home in Ecorse
4.93 out of 5 average rating, 194 reviews

David's Dwelling: Spa-like bathrooms, Full Wetbar!

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Quick stats about vacation rentals in Windsor

  • Total rentals

    1.6K properties

  • Total number of reviews

    77K reviews

  • Family-friendly rentals

    620 properties are a good fit for families

  • Pet-friendly rentals

    400 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    890 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.

  • What types of vacation rentals are available in Windsor?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Windsor. From over 720 house rentals to over 500 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

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

    Yes! Work meets play with ease at over 890 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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