Holiday Rentals in Windsor

2034 available vacation rental offers

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Windsor holiday rentals
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Best Holiday rentals and Airbnb offers in Windsor

Best family friendly Windsor holiday rentals

Among the 2034 accommodations in Windsor, here are the 4 best family friendly rentals

Cozy & Bright Upper Unit; 3bd With Workspace; Free Parking; Private Laundry - Windsor
No reviews

Cozy & Bright Upper Unit; 3bd With Workspace; Free Parking; Private Laundry

apartment, Windsor
This apartment is located in Walkerville, a historic neighbourhood in Windsor, just a short distance from Willistead Manor and a 15-minute drive from the city centre. The area is known for its charming shops, restaurants, and architecture.
This three-bedroom apartment can sleep up to four guests, making it ideal for families or groups of friends. It comes with a fully equipped kitchen, a private laundry room, a jacuzzi, and a 50" TV with high-speed internet.
Charming West Village Townhouse, Steps From Shops And Entertainment. - Windsor
9.2 31 reviews

Charming West Village Townhouse, Steps From Shops And Entertainment.

apartment, Detroit
This charming house is conveniently located in Detroit's downtown area, just a short drive from the Detroit Riverwalk and Belle Isle Aquarium, putting you close to the city's vibrant attractions.
The property has four bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy modern amenities like Wi-Fi, a smart TV, and a fully equipped kitchen, plus a garden, spa, and air conditioning for a relaxing stay.
Beautiful Newly Designed Luxurious Apartment - Windsor
8.5 22 reviews

Beautiful Newly Designed Luxurious Apartment

apartment, Windsor
This apartment in Windsor is conveniently located just 3.1 kilometres from the Windsor International Airport, 3.5 kilometres from GM World, and 4 kilometres from the TCF Center, making it ideal for both business travellers and holidaymakers. Guests have consistently rated this property as excellent for its location, cleanliness, and overall experience.
This one-bedroom apartment offers 19 square metres of space and can comfortably accommodate up to four guests. The apartment features a fully-equipped kitchen with a fridge, microwave, dishwasher, and kettle, along with free Wi-Fi, on-site parking, and air conditioning.
Modern Spacious 1 Bedroom And A Den Home (Lower Unit) - Windsor
8.0 9 reviews

Modern Spacious 1 Bedroom And A Den Home (Lower Unit)

apartment, Windsor
This stylish apartment is situated in South Windsor, just a short drive from LaSalle, Windsor Crossing Mall, and Highway 401, making it an ideal base for exploring the wider region. It has received excellent user ratings, testament to its comfort and convenience.
The spacious two-bedroom property, spanning 139 square metres, comfortably accommodates up to six guests. A range of amenities, including a shared pool, a fully equipped kitchen, and a private terrace, ensure a relaxing and enjoyable stay.

Best Windsor holiday rentals with parking

The Boho Oasis: Deluxe Apartment - Windsor
10 43 reviews

The Boho Oasis: Deluxe Apartment

apartment, Windsor
This Windsor studio apartment, located in a quiet neighbourhood approximately 1.6km from the Detroit River, offers easy access to local amenities and parks.
The self-contained basement apartment sleeps two guests, features a king-size bed, fully equipped kitchen (minus an oven), smart TV, and private parking, all within a luxuriously furnished space blending farmhouse, industrial, and bohemian styles.
Windsor Gem - Pets, Office, Parking. - Windsor
10 17 reviews

Windsor Gem - Pets, Office, Parking.

apartment, Windsor
This Windsor West flat is conveniently located on King Street, offering easy access to local amenities and public transport, with Windsor Castle approximately 2.5 kilometres away.
The self-contained apartment features a king-size bed, a dedicated office space, a fully equipped kitchen including a dishwasher, private parking, and a full basement with laundry facilities, accommodating up to two guests.
"The Modern Loft" In Walkerville / 2bed - 1 Bath - Windsor
9.9 171 reviews

"The Modern Loft" In Walkerville / 2bed - 1 Bath

apartment, Windsor
This modern two-bedroom apartment is situated in Old Walkerville, a historic district in Windsor, just a short walk from restaurants, pubs, and shops, and within 2 km of the Casino Windsor and the city centre.
The apartment features a spacious open-plan living area, a fully equipped kitchen with a fridge, freezer, and microwave, a bathroom with a rainfall shower head, and a private patio, perfect for enjoying a morning coffee or an evening drink.
Gusii- Main Floor, Central Spot, Full 1br Apt, Ac - Windsor
9.4 93 reviews

Gusii- Main Floor, Central Spot, Full 1br Apt, Ac

apartment, Windsor
This Windsor city centre flat is ideally located a 0.8km walk from the city's downtown area, the casino, and the Detroit River waterfront.
The ground-floor apartment sleeps three guests and comprises a bedroom, kitchen with fridge, freezer and microwave, living room, bathroom, and offers parking, air conditioning, and a garden; it's perfect for short or extended stays and includes HST for bookings under 28 days.

Frequently asked questions about holiday rentals in Windsor

  • What are the top family-friendly attractions in Windsor, Ontàrio, Canadà?

    Windsor has plenty for families! The Windsor Sculpture Park is a great outdoor space for kids to run around, and the Chimney Stacks Park features a playground and a splash pad. For something indoors, the Windsor Public Library has a fantastic children's section with interactive exhibits and events.
  • What are the best Airbnb and vacation rentals in Windsor?

  • When is the best time to book a vacation rental in Windsor, Ontàrio, Canadà?

    The best time to book a vacation rental in Windsor is during the shoulder seasons, from April to May or September to October. You'll avoid the peak tourist crowds and enjoy pleasant weather, making it ideal for exploring.
  • What are the most popular Airbnbs in Windsor?

  • What events or festivals should visitors check out in and around Windsor, Ontàrio, Canadà?

    Windsor's calendar is packed with exciting events! The Windsor International Film Festival in November showcases independent films from around the world. In July, the Windsor International Jazz Festival brings a lively atmosphere with live music performances.
  • What are the best vacation rentals with a pool in Windsor?

  • What are the best budget-friendly activities in Windsor, Ontàrio, Canadà?

    For a budget-friendly day out, take a stroll along the Detroit Riverfront, enjoy the beautiful views, and maybe pack a picnic. You can also visit the Windsor Sculpture Park, a free outdoor art gallery, and enjoy the fresh air and artistic installations.
  • What are the best rentals for families and kids in Windsor?

  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of local cuisine, try The Twisted Apron, known for its creative and delicious dishes featuring fresh, local ingredients. Another popular choice is The Colosseum, offering classic Italian dishes with a modern twist.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a popular choice for walkers and cyclists, offering scenic views of the Detroit River. For a longer ride, explore the Windsor-Essex Parkway, a scenic route that winds through the countryside.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    Windsor has a few pet-friendly options. The Windsor Sculpture Park welcomes well-behaved dogs on a leash. Many restaurants also have outdoor patios where you can dine with your furry friend.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy compared to hotels. They often come with kitchens, allowing you to cook your own meals and save money. You can also find rentals in different neighbourhoods, giving you a more local experience.

Popular destinations

Best Windsor holiday rentals with a balcony

3 Bdr Upper, Prime Location - Windsor
No reviews

3 Bdr Upper, Prime Location

apartment, Windsor
This three-bedroom upper-floor flat in Remington Park, Windsor, offers convenient access to amenities, being a short drive from Devonshire Mall and key cross-border attractions like the Detroit-Windsor Tunnel.
This 111 square metre flat accommodates up to five guests with a fully equipped kitchen, air conditioning, and a terrace or balcony, providing a comfortable base for both work and leisure stays near the Chrysler plant.
Spacious Detroit Retreat  Sleeps 16  Parking - Windsor
8.8 3 reviews

Spacious Detroit Retreat Sleeps 16 Parking

apartment, Detroit
This six-bedroom Detroit dwelling, sleeping sixteen, is situated in the West Village, approximately 5 kilometres from Belle Isle and Eastern Market, and a short drive from the city centre.
The 500 sq ft master suite, three bathrooms, fully equipped kitchen, PS5, Ms Pac-Man arcade game, and three smart TVs are among the amenities in this spacious property, ideally suited for large families or groups.
Walk To Motown! Central Detroit Duplex W/ Backyard - Windsor
No reviews

Walk To Motown! Central Detroit Duplex W/ Backyard

house, Detroit
This upstairs duplex in a central Detroit neighbourhood offers a short walk to the historic Motown Museum.
This 269 square metre property sleeps 23 guests across six bedrooms and four bathrooms, featuring a fully equipped kitchen, air conditioning, private parking, and a work desk.
Cozy 4 Bedroom Home Near Tecumseh Mall - Windsor
No reviews

Cozy 4 Bedroom Home Near Tecumseh Mall

apartment, Windsor
This Riverside apartment in Windsor is conveniently located within 1.5 kilometres of Tecumseh Mall and Adventure Bay Family Water Park, offering easy access to shopping, dining and the Detroit Windsor Tunnel.
This 103 square metre flat accommodates up to 11 guests with four bedrooms, two bathrooms, a kitchen equipped with a microwave oven, and a private patio and balcony, alongside street parking for three vehicles.

Best Windsor holiday rentals with air conditioning

Heart Of East Windsor - Windsor
9.3 103 reviews

Heart Of East Windsor

bungalow, Windsor
This charming bungalow is situated just a 5-minute walk from the picturesque Riverside Drive East in Windsor, offering easy access to the riverfront and a peaceful atmosphere. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
This cosy home is perfect for couples or solo travellers seeking a comfortable stay. The bungalow features a fully equipped kitchen with a fridge, air conditioning, and parking, making it a convenient choice for visitors.
Charming Old Walkerville 2-bedroom Luxury Suite - Windsor
9.9 222 reviews

Charming Old Walkerville 2-bedroom Luxury Suite

apartment, Windsor
This two-bedroom apartment is situated in Old Walkerville, a historic district just a short walk from the waterfront and within easy reach of restaurants, shops, and parks. The apartment has consistently received excellent ratings for location, cleanliness, and user experience.
The apartment offers a comfortable and spacious living space for up to four guests. The fully equipped kitchen, air conditioning, and private garden with a deck provide everything you need for a relaxing stay.
Adorable 2  Br House Near Downtown,  2 Discounts - Windsor
9.7 38 reviews

Adorable 2 Br House Near Downtown, 2 Discounts

bungalow, Windsor
This apartment is conveniently located just a short distance from Windsor town centre, offering easy access to shops, restaurants and attractions. It has consistently received excellent ratings from previous guests for its cleanliness, location and overall experience.
The apartment is spacious and can comfortably accommodate up to four guests. Guests can enjoy a range of amenities including a fully equipped kitchen, a private deck, fast internet, Netflix, a washer and dryer, and free parking.
Stylish & Comfortable 6br  Sleeps 16  Parking - Windsor
9.6 51 reviews

Stylish & Comfortable 6br Sleeps 16 Parking

apartment, Detroit
This six-bedroom Detroit dwelling, ideal for large groups, is situated near Woodward Avenue, offering easy access to Midtown, Downtown Detroit, Ford Field, Comerica Park, Little Caesars Arena, and the casinos.
Sleeping up to sixteen guests, the three-storey property boasts two living rooms with smart TVs, a fully equipped kitchen, a first-floor half-bathroom, in-unit laundry, and a garden with parking.
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