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Vacation rentals in Windsor

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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

Monthly stays
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Stay near Windsor's top sights

Little Caesars Arena303 locals recommend
Ford Field294 locals recommend
Detroit Institute of Arts746 locals recommend
Eastern Market369 locals recommend
Campus Martius Park District320 locals recommend
Motown Museum388 locals recommend

Windsor house rentals

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, 157 reviews

Quiet LaSalle Newly Renovated Entire Country Home

Guest favorite
The exterior of a modern two-story home is illuminated at dusk, showcasing a welcoming terrace area with stairs leading to the entrance. The building features a mix of wood and metal elements, surrounded by landscaped areas and a spacious driveway.
Home in Belle River
5 out of 5 average rating, 10 reviews

Key West Cottage

Guest favorite
A spacious living area features a comfortable sectional sofa and an ottoman. Large glass doors provide a view of Lake Erie. A natural wood TV stand and wall art accents are present, along with a patterned area rug and a touch of greenery from a nearby plant.
Home in Kingsville
4.92 out of 5 average rating, 238 reviews

Heritage Lakehouse

Top guest favorite
A modern two-story home displays a light grey façade with a distinct peaked roof. A large central entrance is framed by elegant stone accents. A vehicle is parked in the driveway, while the surrounding area features unlandscaped grounds and nearby homes, enhancing the neighborhood feel.
Home in Riverside
5 out of 5 average rating, 35 reviews

Happy Trails Inn

Guest favorite
The exterior of a single-story brick house is presented, featuring a small front porch with steps leading to a black railing. A fenced area is visible, with a grassy yard and a paved driveway extending towards the front. Nearby, trash bins are placed along the curb.
Home in Windsor
4.87 out of 5 average rating, 149 reviews

Full house - 5 bed, 2 bath

Guest favorite
The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.
Home in LaSalle
4.91 out of 5 average rating, 115 reviews

The Ambassador Estate Inn

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
4.95 out of 5 average rating, 100 reviews

little cozy house 2 bedroom

Superhost
A modern living area features a light blue accent wall, a large flat-screen television mounted above a white desk with a chair. A cozy sofa is adorned with bright orange throw pillows. A small plant adds a touch of greenery, while a doorway leads to another space.
Home in The Core
4.77 out of 5 average rating, 13 reviews

Cozy Quiet Home Away

Other great vacation rentals in Windsor

Guest favorite
The loft showcases an open living space with warm wooden floors and a cozy sofa. A stylish chandelier hangs above the kitchen area, which features wooden cabinetry and colorful tile accents. A kitchen island is positioned near the seating area, providing an inviting space for dining or working.
Loft in The Core
4.94 out of 5 average rating, 104 reviews

OldeWalkerville Loft Gem on the River

Guest favorite
A modern living area features a plush orange sofa facing a wall-mounted television. Natural light enters through large windows, which are framed by light grey curtains. A neutral-toned area rug lies beneath a coffee table, enhancing the spacious feel of the room.
Apartment in Windsor
4.84 out of 5 average rating, 57 reviews

Rare find by the Riverside

Superhost
Home in Windsor
5 out of 5 average rating, 3 reviews

Adorable 2 Bedrooms Unit Near Riverside

Guest favorite
A well-lit sleeping area features a spacious bed with crisp white linens and decorative pillows. Two soft-lit lamps illuminate the bedside, and green plants add a natural touch. A serene artwork hangs above the bed, depicting a boat against a tranquil background.
Home in The Core
4.92 out of 5 average rating, 74 reviews

Cheerful & cozy downtown 2-bedroom home

Top guest favorite
A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.
Guest suite in Windsor
4.9 out of 5 average rating, 80 reviews

Private/Quiet Perfect for professionals!

Top guest favorite
A spacious studio apartment features a large, inviting bed dressed in light linens. Complemented by a round wooden table and a wicker chair, the room is adorned with decorative wall hangings and plants. Soft lighting creates a serene ambiance throughout the space.
Apartment in Windsor
5 out of 5 average rating, 25 reviews

The Boho Oasis: Deluxe Apartment

Guest favorite
A spacious backyard is presented, showcasing a hot tub situated on a concrete pad. Green grass lines the space, complemented by wooden fencing and ambient lighting. A small tree is visible in the corner, and utility lines are present in the sky against a colorful sunset backdrop.
Home in The Core
4.95 out of 5 average rating, 87 reviews

Modern Walkerville Gem | HotTub & Cozy Backyard

Superhost
A modern retreat is highlighted by a sleek, heated pool reflecting the evening sky. Floor-to-ceiling windows provide glimpses of illuminated indoor spaces, while a rooftop terrace is accessible. A landscaped patio is bordered by a wooden fence, offering privacy.
Home in Windsor
4.53 out of 5 average rating, 15 reviews

Architectural Gem | Direct-Entry Pool

Quick stats about vacation rentals in Windsor

  • Total rentals

    1.6K properties

  • Total number of reviews

    81K reviews

  • Family-friendly rentals

    650 properties are a good fit for families

  • Pet-friendly rentals

    390 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    910 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 pet-friendly vacation rentals in Windsor?

    Four-legged friends are welcome in Windsor. Choose from more than 390 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 910 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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