Holiday Rentals in Windsor

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Windsor holiday rentals
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Best Holiday rentals and Airbnb offers in Windsor

Search Holiday Rentals near the Heart of the City in Windsor

Plan a secluded urban getaway at self-catering holiday rentals for couples in Windsor, providing great layouts for two.

Serene Green 2br Haven In Little Italy W/ Parking - Windsor
9.6 70 reviews

Serene Green 2br Haven In Little Italy W/ Parking

apartment, Windsor
This Windsor apartment rental is conveniently located within a 5-10 minute walk of Italian restaurants and shops, offering easy access to Windsor city centre, the Detroit border, Highway 401, and Windsor Regional Hospital.
The two-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen with stainless steel appliances, complimentary breakfast items, free on-street parking, a private basement laundry with an additional bathroom, a fully fenced backyard, and high-speed Wi-Fi, plus smart lock for self check-in.
Walk To Caesars Casino Sleeps 8 Hot Tub 2 Parking - Windsor
9.6 28 reviews

Walk To Caesars Casino Sleeps 8 Hot Tub 2 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.
482# Cheapest Great Home, Walk To Casino Tunnel - Windsor
9.0 833 reviews

482# Cheapest Great Home, Walk To Casino Tunnel

apartment, Windsor
This apartment is located in Windsor, just a short walk from the Detroit Riverside Park and within a couple of kilometres of Caesar's Casino and the city centre. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The flat has two bedrooms and one bathroom, comfortably accommodating up to five guests. It offers amenities like air conditioning, a garden, parking, and a kitchen equipped with a fridge and microwave, making it ideal for families and groups looking for a comfortable stay.
Windsor Casino And International Swim Meet Airbnb - Windsor
10 31 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.

Best Windsor holiday rentals with air conditioning

Spacious 4br Home In Walkerville With Bbq & Parking - Windsor
9.0 1 review

Spacious 4br Home In Walkerville With Bbq & Parking

apartment, Windsor
This 4-bedroom, 2-bathroom family-friendly flat is located in Walkerville, Windsor, a district known for its historical architecture, offering convenient access to local attractions.
This self-catering accommodation provides a modern kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, a terrace, and private parking, with a guest capacity of 15.
Heart Of East Windsor - Windsor
9.3 105 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.
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.
Charming 2-bdr Unit | Backyard  Deck  Parking - Windsor
10 12 reviews

Charming 2-bdr Unit | Backyard Deck Parking

apartment, Windsor
This upper unit flat is located in a quiet residential area of Windsor, a short drive from downtown attractions, restaurants, shops, and the riverfront.
This accommodation offers 2 bedrooms, 1 bathroom, and a guest capacity of 4, featuring a spacious backyard with a deck, a smart TV in the living room, a fully equipped kitchen with a smart fridge, in-unit laundry, and private driveway parking.

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 should definitely check out the Windsor Sculpture Park, a free outdoor gallery with fascinating contemporary sculptures. You can also visit the Ojibway Nature Centre, a beautiful natural area with walking trails, a butterfly garden, and a nature centre.
  • What are the best Airbnb and holiday rentals in Windsor?

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

    The Walkerville neighbourhood is a great choice for a vacation rental. It's a historic district with charming Victorian architecture, trendy restaurants, and art galleries. It's also close to the Detroit River and the downtown core.
  • What are the most popular Airbnbs in Windsor?

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

    For families, the Windsor Sculpture Park is a great place to visit. There's also the Chimczuk Museum, which has interactive exhibits on science and technology. And for a fun day out, you can visit the Adventure Bay Family Waterpark, a large water park with slides, pools, and a wave pool.
  • What are the best holiday rentals with a pool 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 and September to October. You'll find better deals on rentals and fewer crowds, but you'll still be able to enjoy the pleasant weather.
  • What are the best rentals for families and kids in Windsor?

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

    The Windsor International Film Festival is a great event to catch in late November, showcasing a range of films from around the world. In the summer, there's the Windsor International Jazz Festival, featuring live music performances from local and international artists.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor?

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

    For a budget-friendly activity, take a stroll along the Detroit Riverfront. You can also visit the Windsor Sculpture Park, which is free to enter. If you're looking for a unique experience, visit the Art Gallery of Windsor, which offers free admission on the first Sunday of every month.
  • What are the best restaurants with local dishes in Windsor, Ontàrio, Canadà?

    For a taste of local cuisine, check out The Twisted Apron, a popular restaurant known for its fresh, locally sourced ingredients. Another great option is The Colosseum, a classic Italian restaurant that's been serving Windsor for over 50 years.
  • What are the best walking or cycling routes in Windsor, Ontàrio, Canadà?

    The Riverfront Trail is a popular walking and cycling route that runs along the Detroit River. You can also explore the trails at the Ojibway Nature Centre, which offer stunning views of the natural landscape.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    Yes, there are several pet-friendly attractions in Windsor. The Windsor Sculpture Park is dog-friendly, and you can often spot dogs enjoying the trails at the Ojibway Nature Centre.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy than hotels. They're also often located in residential areas, giving you a more authentic experience of the city. And if you're travelling with a family or group, vacation rentals can be a more cost-effective option.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    Windsor is home to the WFCU Centre, a multi-purpose arena that hosts a variety of sporting events, including ice hockey and basketball. The city also has several public parks with sports fields, tennis courts, and swimming pools.

Popular destinations

Top Holiday Rentals with a Balcony in Windsor

Private balconies with city skyline views come as standard at these holiday rentals in Windsor for a lovely start to your day.

The Windsor Loft - Windsor
No reviews

The Windsor Loft

apartment, Windsor
This two-bedroom flat is situated in Windsor's Bridgeview district, offering convenient access to the downtown core, dining, and shopping, and is located directly opposite a family-friendly park, with the Fox Theatre and Henry Ford Museum a short distance away.
This modern apartment boasts an open-concept living space, a fully equipped kitchen, a private ensuite bathroom, and fast Wi-Fi, with the Detroit Windsor Tunnel and Ambassador Bridge also nearby for easy travel.
Lumber Barons Detroit Brush Park Penthouse 3br 2 Kings 1 Queen 2 Baths 1 Car Garage - Windsor
9.6 6 reviews

Lumber Barons Detroit Brush Park Penthouse 3br 2 Kings 1 Queen 2 Baths 1 Car Garage

apartment, Detroit
This penthouse flat is situated in Detroit's historic district, just 800 metres from the Masonic Temple Theatre and 2.6 kilometres from the TCF Center. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This spacious three-bedroom, two-bathroom property spans 251 square metres and comfortably accommodates up to seven guests. Enjoy a fully equipped kitchen, a private patio with garden views, complimentary Wi-Fi, on-site parking, and a range of entertainment options including a flat-screen TV with streaming services.
Modern & Private 1-bedroom Apartment - Windsor
9.4 79 reviews

Modern & Private 1-bedroom Apartment

apartment, Windsor
This modern flat is situated in Windsor, just 3km from the TCF Center and 2.5km from GM World, offering easy access to the city's attractions. The property has received excellent ratings for cleanliness and user experience, and a very good rating for location.
The flat can accommodate up to 4 guests and features a private entrance, balcony, and a fully equipped kitchen. Guests can enjoy amenities such as free private parking, air conditioning, and access to a garden, making it a comfortable and convenient base for exploring Windsor.
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.

Explore Holiday Rentals for Families in Windsor

Travelling to Windsor with children? A quality family holiday rental or Airbnb makes everything easier with city attractions nearby.

Charming West Village Townhouse, Steps From Shops And Entertainment. - Windsor
9.2 33 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.
Papa's Place Urban Cottage Retreat - Windsor
9.6 33 reviews

Papa's Place Urban Cottage Retreat

apartment, Detroit
Papa's Place is a centrally located flat in Detroit, just a 10-minute drive from the city centre and within walking distance of the Motown Museum, Dbads outdoor museum, and the New Centre Area. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom apartment comfortably sleeps four guests and is equipped with a modern kitchen, air conditioning, and a terrace or balcony. Enjoy the garden, parking, and internet access, along with the unique blend of historic charm and modern comfort this renovated 1913 home offers.
Lumber Barons Brush Park Penthouse - 3br - 2 Kings/queen/2.5bath - 1-car Garage - Windsor
10 43 reviews

Lumber Barons Brush Park Penthouse - 3br - 2 Kings/queen/2.5bath - 1-car Garage

apartment, Detroit
This apartment is situated on the top floor of a restored historic mansion in the Brush Park neighbourhood of Detroit, just a short walk from the Detroit Institute of Arts, Comerica Park, Little Caesars Arena, and the Fox Theatre. It has received excellent reviews from previous guests.
The apartment has three bedrooms and three bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace, and parking, as well as free internet access and multiple TVs with streaming services.
Hidden Gem Steps From River, Restos, Cafés, Parks - Windsor
No reviews

Hidden Gem Steps From River, Restos, Cafés, Parks

house, Windsor
This Windsor apartment is located a short distance from the river, offering convenient access to local eateries, coffee shops, and green spaces, with the TCF Centre 5.5 kilometres away and GM World 4.8 kilometres away.
This pet-friendly property accommodates up to nine guests and features a private balcony with garden views, complimentary private parking, free WiFi, and air conditioning, alongside a fully equipped kitchen for self-catering.

Popular Holiday Rentals with Parking in Windsor

Park up and enjoy the city centre. These holiday rentals in Windsor come with a free car park on-site. Start comparing now.

Luxurious Home In Windsor - Windsor
9.7 54 reviews

Luxurious Home In Windsor

apartment, Windsor
New Construction Bright, Modern 2 Bedroom Unit. - Windsor
9.3 14 reviews

New Construction Bright, Modern 2 Bedroom Unit.

apartment, Windsor
The Ambassadors Stay  Bright 1br Family Retreat - Windsor
9.7 239 reviews

The Ambassadors Stay Bright 1br Family Retreat

apartment, Windsor
Welcome To Our Home - Windsor
10 5 reviews

Welcome To Our Home

apartment, Windsor

Handpicked Luxury Holiday Rentals in Windsor

A city-centre luxury holiday rental or Airbnb in Windsor sets the perfect tone for your stay. Expect 5-star comfort and quality throughout.

Welcome To Woodlawn - Windsor
9.7 44 reviews

Welcome To Woodlawn

apartment, Windsor

Our Favourite Dog-Friendly Self-Catering Holiday Rentals in Windsor

No need to leave your dog behind in Windsor. Our holiday rentals offer proximity to dog parks and lovely city walks.

Stay On Larkin - Windsor
9.9 37 reviews

Stay On Larkin

apartment, Windsor
East Grand Marrakesh - Windsor
10 6 reviews

East Grand Marrakesh

apartment, Detroit
Stylish Walkerville Stay | Workspace + Prime Location - Windsor
No reviews

Stylish Walkerville Stay | Workspace + Prime Location

apartment, Windsor
Walkerville 1br Suite | Parking, Laundry & Wifi - Windsor
No reviews

Walkerville 1br Suite | Parking, Laundry & Wifi

apartment, Windsor

Compare Holiday Rentals with a Pool in Windsor

These holiday rentals and Airbnbs in Windsor include a pool, so a proper swim in the heart of the city is always on the cards.

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
Spacious Family Getaway W/ Pool -Sleeps 12 - 2 Tvs - Windsor
9.9 56 reviews

Spacious Family Getaway W/ Pool -Sleeps 12 - 2 Tvs

apartment, Windsor
Enjoy Your Own Private Pool And Backyard Oasis In Windsor - Windsor
No reviews

Enjoy Your Own Private Pool And Backyard Oasis In Windsor

apartment, Windsor
The River Condos - Windsor
No reviews

The River Condos

apartment, Detroit

Top-Rated Self-Catering Holiday Rentals with a Jacuzzi in Windsor

A holiday rental with a hot tub in Windsor is perfect for unwinding in private after exploring the city. Browse our top-rated options.

The Victorian On Victoria - Windsor
9.2 22 reviews

The Victorian On Victoria

apartment, Windsor
3-bedroom Condo Quiet And Secure In An Upscale Neighborhood Downtown Detroit. - Windsor
9.6 4 reviews

3-bedroom Condo Quiet And Secure In An Upscale Neighborhood Downtown Detroit.

apartment, Detroit
Walk To Riverfront & Caesars Casino  Free Parking - Windsor
9.2 120 reviews

Walk To Riverfront & Caesars Casino Free Parking

apartment, Windsor
Gorgeous 9-bedroom Historic Estate With Ac In Vibrant Detroit - Windsor
No reviews

Gorgeous 9-bedroom Historic Estate With Ac In Vibrant Detroit

apartment, Detroit
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