Holiday Rentals in Windsor

1448 available vacation rental offers

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Windsor holiday rentals
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Windsor holiday rentals: compare the best deals

Best family friendly Windsor holiday rentals

Among the 1448 accommodations in Windsor, here are the 4 best family friendly rentals

The Victorian On Victoria - Windsor
9.2 22 reviews

The Victorian On Victoria

apartment, Windsor
This Windsor city centre house is less than 2km from Caesars Windsor and a short walk from the Chrysler Theatre and the Detroit-Windsor Tunnel.
Sleeping seven guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, private patio, hot tub, garden, and free Wi-Fi.
Walk To Caesar Riverfront Sleeps 8 Hot Tub Parking - Windsor
9.5 16 reviews

Walk To Caesar Riverfront Sleeps 8 Hot Tub Parking

apartment, Windsor
This stylish downtown Windsor flat offers excellent access to Caesars Casino, the riverfront, and a range of dining and entertainment options, all within a short walk.
This property sleeps up to eight guests and features two bedrooms, one bathroom, air conditioning, a fully equipped kitchen, on-site parking for two vehicles, and an optional private hot tub spa for an additional fee.
Executive Home In Windsor Close To The Airport - Windsor
9.7 14 reviews

Executive Home In Windsor Close To The Airport

house, Windsor
This executive house in Windsor is situated 1.9km from Windsor International Airport and within a 11-12km radius of major Detroit attractions including the TCF Centre and the Detroit Symphony Orchestra.
The 300 square metre property boasts one bedroom, two bathrooms, and sleeps seven guests, offering free Wi-Fi, private parking, a fully equipped kitchen with dishwasher, and a washing machine.
Windsor Perfect Stay - Windsor
8.4 16 reviews

Windsor Perfect Stay

apartment, Windsor
This Windsor flat offers convenient access, situated approximately 4 kilometres from Windsor International Airport and within 8 kilometres of the TCF Centre, Music Hall Centre, and Saint Andrew's Hall.
This serviced apartment for seven guests features complimentary Wi-Fi, air conditioning, a well-equipped kitchen, and private parking, with a picnic area available for outdoor relaxation.

Best Windsor holiday rentals with parking

Eastern Market Love - Windsor
9.8 100 reviews

Eastern Market Love

apartment, Detroit
This one-bedroom apartment is located in Detroit's Eastern Market district, just a short walk from coffee shops, restaurants and the Saturday farmers market, and within 2km of Ford Field, Comerica Park and Little Caesars Arena. The surrounding area has a lively atmosphere, offering a taste of Detroit's unique energy and charm.
The apartment can accommodate up to eight guests and has a fully equipped kitchen with a fridge, freezer and dishwasher. Guests can enjoy the garden, fitness centre, and secure parking, as well as explore the city on bicycles or skateboards provided.
Stylish 2br 1 Bath Haven With Wifi & Parking - Windsor
No reviews

Stylish 2br 1 Bath Haven With Wifi & Parking

apartment, Windsor
This two-bedroom flat is situated in Windsor's historic Sandwich district, offering convenient access to attractions such as the Fox Theatre and Greenfield Village, with the Detroit Windsor Tunnel just a short distance away for cross-border travel.
This 55 square meter residence accommodates up to four guests, featuring a well-equipped kitchen, air conditioning, private parking for one vehicle, and complimentary high-speed Wi-Fi, with a shared laundry facility available for added convenience.
Downtown Detroit 1bd Apt Wlk- Dmc, Wayne State, Ford Field, Comerica Prk, Arena - Windsor
10 5 reviews

Downtown Detroit 1bd Apt Wlk- Dmc, Wayne State, Ford Field, Comerica Prk, Arena

apartment, Detroit
This one-bedroom flat in Brush Park, Downtown Detroit, is centrally located within 500 metres of the Detroit Medical Centre, Little Caesars Arena, Ford Field, and Comerica Park.
This flat for four guests offers a fully equipped kitchen, a queen bed, a queen pull-out sofa, on-site laundry facilities, and complimentary high-speed Wi-Fi, with Whole Foods and other amenities nearby.
Oldewalkerville Loft Gem On The River - Windsor
9.9 114 reviews

Oldewalkerville Loft Gem On The River

apartment, Windsor
This Windsor studio apartment, situated in the historic Olde Walkerville district directly on the River Walk trail, offers easy access to the Detroit River and its scenic views.
The 74-square-metre (800 sq ft) open-plan flat features a private deck, designated parking, high-speed internet, laundry facilities, and accommodates two guests, with a fully equipped kitchen including a dishwasher and microwave.

Frequently asked questions about holiday rentals in Windsor

  • What should a first-time visitor not miss in Windsor, Ontàrio, Canadà?

    For a first-time visit, you'd want to check out the iconic Windsor Sculpture Park, with its impressive collection of modern art. Don't miss the chance to explore the historic Fort Malden National Historic Site, offering a glimpse into the region's rich past.
  • What are the best Airbnb and vacation rentals in Windsor?

  • Which neighborhood in Windsor, Ontàrio, Canadà should you consider for a vacation rental?

    The Olde Walkerville neighbourhood is a popular choice for vacation rentals. It's known for its charming Victorian architecture, lively restaurants, and proximity to the Detroit River.
  • What are the most popular Airbnbs in Windsor?

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

    Booking your vacation rental in advance is always recommended, especially during peak seasons like summer and the autumn months. You'll have a wider selection and potentially better prices.
  • What are the best vacation rentals with a pool in Windsor?

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

    The annual Windsor International Film Festival in November is a highlight, showcasing independent films. In June, the Windsor International Blues Festival brings live music and a vibrant atmosphere to the city.
  • What are the best rentals for families and kids in Windsor?

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

    A stroll along the scenic Detroit River Walk is a great free activity, offering beautiful views and fresh air. The Windsor Public Library is another budget-friendly option, hosting free events and providing access to books and resources.
  • What are the best rentals or Airbnbs with a jacuzzi 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 innovative dishes featuring fresh, seasonal ingredients. The Old Stone Tavern offers a traditional pub atmosphere and classic comfort food.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a popular choice for both walking and cycling, offering stunning views of the Detroit River. The University of Windsor campus also has a network of well-maintained walking and cycling paths.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    The Windsor Sculpture Park welcomes well-behaved dogs on leash. The Detroit River Walk is also a great option for a stroll 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 amenities like kitchens and laundry facilities, making them a convenient option for families or longer stays.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is home to the Windsor Spitfires, a junior ice hockey team. For outdoor activities, Dieppe Park offers a range of sports facilities, including tennis courts and a baseball diamond.

Popular destinations

Best Windsor holiday rentals with a balcony

The Bachelor Suite At Stanley/kitchenette&backyard - Windsor
No reviews

The Bachelor Suite At Stanley/kitchenette&backyard

apartment, Windsor
This Remington Park flat in Windsor offers a private patio overlooking a tranquil backyard, conveniently located near Devonshire Mall with easy access to Windsor city centre, the airport, and the US border crossings.
The self-contained apartment sleeps two, featuring a king-size bed and futon, a well-equipped kitchenette including an air fryer, a 32-inch LG Smart TV, and a dedicated workspace; proximity to attractions such as the Fox Theatre, the Detroit-Windsor Tunnel, and the Ambassador Bridge adds further appeal.
Cozy 4 Bedroom Home Near Tecumseh Mall - Windsor
No reviews

Cozy 4 Bedroom Home Near Tecumseh Mall

house, Windsor
This four-bedroom detached house is located in a quiet Windsor neighbourhood, offering convenient access to Tecumseh Mall, shops, restaurants, and grocery stores, all within 1 kilometre.
The property spans 102 square meters and accommodates up to six guests with four bedrooms, two bathrooms, a fully equipped kitchen featuring a microwave and freezer, and a private garden with a patio and balcony, alongside street parking for three vehicles.
Unique 2-bdr Historic Warehouse Loft With Terrace ! ! ! - Windsor
9.6 39 reviews

Unique 2-bdr Historic Warehouse Loft With Terrace ! ! !

apartment, Windsor
The Warehouse apartment in Windsor offers a spacious two-bedroom flat, conveniently located approximately 2.7km from Saint Andrew's Hall and within a 3.2km radius of other attractions including the Music Hall Centre and the TCF Centre.
This 102 square metre Windsor property sleeps up to nine guests and boasts a terrace with river views, a garden, tennis court, parking, and a well-equipped kitchen; on-site amenities include a children's playground and a casino.
The Boho Oasis: Luxurious Studio Apartment, Quiet Court, Close To All Amenities! - Windsor
10 33 reviews

The Boho Oasis: Luxurious Studio Apartment, Quiet Court, Close To All Amenities!

studio, Windsor
This East Windsor flat is ideally located within a 4.8km radius of Coventry Gardens, the Olde Walkerville neighbourhood, Willistead Manor, and the Windsor Riverfront.
The 42 square metre self-catering apartment, sleeping one guest, boasts a fully equipped kitchen, free Wi-Fi, a private bathroom, and access to an on-site swimming pool, spa, and water park.

Best Windsor holiday rentals with air conditioning

Stylish 2bd  Dt Laundry And Parking - Windsor
No reviews

Stylish 2bd Dt Laundry And Parking

apartment, Windsor
This Windsor city centre apartment is conveniently located within a 15-minute walk (approximately 1.2km) of the Windsor Community Museum, the Detroit-Windsor Tunnel, and Caesars Windsor.
This 150 square metre self-catering flat sleeps six guests in three bedrooms and two bathrooms, and boasts a private balcony, fitness centre access, and a swimming pool within the building.
Quiet, Cozy Private Suite W/ Separate Entrance - Windsor
10 5 reviews

Quiet, Cozy Private Suite W/ Separate Entrance

house, Windsor
This private main floor apartment is located in a quiet Windsor neighbourhood, offering convenient access to the Gordie Howe International Bridge and local amenities, with the bridge approximately 1.6 kilometres away.
This self-contained unit features one bedroom and one bathroom, accommodating up to two guests, and includes internet, air conditioning, kitchen facilities, and parking, with shared access to a backyard.
Windsor Casino And International Swim Meet Airbnb - Windsor
10 19 reviews

Windsor Casino And International Swim Meet Airbnb

apartment, Windsor
This newly renovated Windsor residence offers a 700 sqft second-floor suite, situated in the Ouellette entertainment district, a mere 100 metres from the Casino and 400 metres from Ouellette Avenue's bars and restaurants.
This pet-friendly, family-approved flat accommodates up to eight guests with three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, and a private, fenced garden, alongside free on-site parking.
Cozy River Side Retreat U Of W & Ambassador Bridge - Windsor
10 2 reviews

Cozy River Side Retreat U Of W & Ambassador Bridge

apartment, Windsor
This 3-bedroom flat in Windsor is ideally located just 500 metres from the University of Windsor and within easy reach of the Ambassador Bridge for cross-border travel, with Riverside Drive offering scenic waterfront access.
This modernised apartment accommodates up to six guests and features a newly renovated kitchen and bathroom, complimentary on-site parking, private entry, and laundry facilities, with restaurants, cafés, and grocery stores all within walking distance.
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