This studio apartment is situated in Downtown Windsor, a short 600 metres from the University of Windsor and convenient for exploring local restaurants, entertainment, and the U.S. border crossing. This modern studio offers accommodation for two guests with a fully equipped kitchen including a fridge and microwave, air conditioning, on-site parking, and in-suite laundry facilities.
Windsor
01/07 – 31/07
SG$73/nighttotal: SG$2190 (30 )
Affordable And Reliable
2 5
apartment , Windsor
This apartment in Windsor offers a peaceful retreat with convenient access to local amenities and attractions. This two-bedroom flat accommodates up to five guests and features air conditioning, internet, and a kitchen, with a 2017 white Nissan Qashqai Rogue Sport available for rent via Turo.
9.9 27 reviews
Windsor
25/06 – 27/06
SG$341/nighttotal: SG$682 (2 )
Perfect Stay! 4 Bdr In East End
1 5
apartment , Windsor
This four-bedroom Windsor house enjoys a peaceful riverside location on a quiet street, minutes (distance unspecified) from local parks, shopping areas, the new battery plant, and the WFCU Centre. The self-catering property offers ample space for six guests, boasting a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and two bathrooms.
Windsor
10/08 – 16/08
SG$119/nighttotal: SG$714 (6 )
Newly Renovated 3 Bedroom Unit
1 2
apartment , Windsor
This newly renovated three-bedroom flat in Windsor offers convenient access to downtown Detroit attractions, situated within a few kilometres of major venues such as the TCF Centre (4.3 km) and The Fillmore Detroit (5.1 km), and is 8 km from Windsor International Airport. This apartment accommodates up to nine guests and features air conditioning, complimentary WiFi, a fully equipped kitchen, and parking, making it ideal for self-catering stays.
9.8 140 reviews
Windsor
03/07 – 05/07
SG$339/nighttotal: SG$678 (2 )
Family-sized 3br • 5 Beds • Near Downtown
1 6
apartment , Windsor
This 3-bedroom house is located in a quiet residential neighbourhood just 2 kilometres from Windsor city centre, making it easy to explore the town's attractions, restaurants and shops. The property has received excellent ratings for its cleanliness, location and overall experience. The house provides ample space for families or groups of up to 8 guests, with a dedicated kids' space in the basement. The property offers a range of amenities including a fully equipped kitchen, air conditioning, a large backyard with BBQ facilities, and private parking for up to three cars.
Windsor
28/06 – 31/07
SG$81/nighttotal: SG$2673 (33 )
1 Bed 1 Bath Backyard Home With Kitchen & Laundry
1 2
apartment , Windsor
This private backyard flat is located in Windsor, offering convenient access to local shops, dining, and attractions, with free street or onsite parking available. This self-contained unit accommodates two guests and features a fully equipped kitchen with a fridge, freezer, and microwave, a dedicated workspace with Wi-Fi, and a comfortable bedroom with a stylish bathroom.
Windsor
26/06 – 27/06
SG$188/nightfor 1 night
Elegant Home 10 Mins Drive To Detroit And Windsor Border And 3mins Drive To Windsor Airport
2 2
apartment , Windsor
This Windsor flat is conveniently located for cross-border travel, just a 3-minute drive from Windsor International Airport and within easy reach of Detroit attractions including the TCF Centre (10.3 km) and Gm World (9.7 km). This 13 square metre, two-bedroom, one-bathroom property offers accommodation for up to 10 guests, featuring a fully equipped kitchen with a dishwasher, air conditioning, and complimentary WiFi and private parking.
9.6 175 reviews
Windsor
17/07 – 20/07
SG$219/nighttotal: SG$657 (3 )
3 Bed | Prime Walkerville | Close To City Center
3 1
apartment , Windsor
This apartment is located in Walkerville, a popular area in Windsor, just 1.5 km from the city centre and close to excellent restaurants. It has received excellent ratings for location, cleanliness and overall experience. The apartment has three bedrooms and can accommodate up to six guests. It features a fully equipped kitchen, a modern bathroom with heated floors, laundry facilities, a private backyard and parking.
9.6 97 reviews
Windsor
01/10 – 31/12
SG$107/nighttotal: SG$9737 (91 )
Roof Top 2-bedroom Penthouse ! ! !
1 2
apartment , Windsor
This downtown Windsor penthouse apartment is minutes from the Detroit-Windsor Tunnel and the Detroit River, offering easy access to numerous restaurants and bars. The two-bedroom, one-bathroom flat boasts a rooftop patio with a gas BBQ, a washer/dryer, and a walk-in shower, comfortably sleeping four guests and including access to a downstairs cigar lounge.
10 2 reviews
Windsor
30/07 – 30/08
SG$165/nighttotal: SG$5115 (31 )
2 Bedrooms Escape | Calm Neighborhod,near The Mall
1 3
apartment , Windsor
This Windsor flat is located in a convenient district, offering easy access to local attractions and amenities. Accommodating up to four guests, this residence features two bedrooms with a Queen and two Twin beds, a spacious living room, a dining area, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and garden access.
9.0 11 reviews
Windsor
27/06 – 04/07
SG$123/nighttotal: SG$861 (7 )
Cozy Comfort Lower Level Unit
2 2
apartment , Windsor
This Roseland, Windsor flat offers guests a self-contained first-floor apartment in a shared building, conveniently located near the Fox Theatre and The Colosseum. The two-bedroom, one-bathroom property sleeps four, boasting a kitchen with fridge and microwave, air conditioning, parking, internet access, and a shared spa, with nearby opportunities for water sports and access to the South Windsor Recreation Complex and Ambassador Golf Club.
9.9 36 reviews
Windsor
30/06 – 02/07
SG$244/nighttotal: SG$488 (2 )
Stay On Larkin
1 6
apartment , Windsor
This family-friendly Windsor Airbnb, ideally situated in a central location, offers easy access to Windsor Castle and other attractions. The two-bedroom, two-bathroom house sleeps six, boasts a fully fenced garden, and includes amenities such as a dishwasher, microwave, and a range of board games and family entertainment options.
Best family friendly Windsor holiday rentals
Among the 1448 accommodations in Windsor, here are the 4 best family friendly rentals
9.4 78 reviews
Windsor
15/12 – 28/12
SG$180/nighttotal: SG$2340 (13 )
Stunning 3 Bedroom Single Family Home.
3 4
apartment , Windsor
This three-bedroom home is situated along the Little River Corridor in Windsor, just a short drive from the city centre and the Detroit River. It has received excellent ratings for location, cleanliness and user experience. The property is spacious at 111 square metres and features a fully equipped kitchen, a private deck and a fenced garden. Enjoy modern amenities such as air conditioning, a washer and dryer, and a Samsung Smart TV Plus, as well as the peace of mind provided by a Ring Smart Home Security system.
10 53 reviews
Windsor
01/10 – 31/12
SG$136/nighttotal: SG$12376 (91 )
Brand New Riverside Retreat | Stylish 2br +Parking
1 2
apartment , Windsor
This luxury apartment is conveniently located just off Riverside Drive in Windsor, placing you within easy reach of the city centre and its attractions, including the Detroit-Windsor Tunnel, just 2km away. Guests consistently rate the apartment as excellent for its location, cleanliness, and overall experience. The apartment is ideal for families or groups of up to four, featuring two queen-sized beds and a well-equipped kitchen. Enjoy high-end amenities like a Jacuzzi, a private garden, and air conditioning, ensuring a comfortable and relaxing stay.
8.4 6 reviews
Windsor
25/06 – 27/06
SG$563/nighttotal: SG$1126 (2 )
Modern Spacious 1 Bedroom And A Den Home (Lower Unit)
2 5
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.
10 1 review
Windsor
29/07 – 04/08
SG$302/nighttotal: SG$1812 (6 )
Matchette Manor - Luxury Hideaway Flat - Lasalle
2 2
apartment , Windsor
This Windsor flat, Matchette Manor - Luxury Hideaway Flat - Lasalle, is located approximately 12.9 kilometres from GM World, Saint Andrew's Hall, and Windsor International Airport. This air-conditioned apartment offers 1760 square metres of floor area, accommodates up to 11 guests with 2 bedrooms and 1 bathroom, and features a fully equipped kitchen with an oven, a private patio, and a garden, with complimentary WiFi and private entrance.
Best Windsor holiday rentals with parking
8.6 10 reviews
Windsor
26/06 – 18/07
SG$357/nighttotal: SG$7854 (22 )
Luxury 1 Bedroom, 1 Bath Apt. In The Middle Of Downtown Detroit W/parking Spot!
1 4
apartment , Detroit
This Detroit city centre apartment is ideally located within a 5-minute walk of Campus Martius Park and Greektown Casino, and 15 minutes from the Renaissance Center and Huntington Place. The one-bedroom, one-bathroom property sleeps four guests and features a fully equipped kitchen with fridge, microwave, oven and hob, plus a dryer, Smart TV and coffee maker; free Wi-Fi is also provided.
9.8 208 reviews
Windsor
25/06 – 27/06
SG$328/nighttotal: SG$656 (2 )
Year Round Hot Tub At The Gem!
1 3
apartment , Windsor
This semi-detached home is situated in a quiet residential neighbourhood in Windsor, just a short drive from the Detroit River and the city centre. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. This spacious dwelling comfortably accommodates up to eight guests with three bedrooms, four beds, and two living areas. The fully equipped kitchen, complete with a Keurig coffee machine, blender, and dishwasher, is perfect for self-catering, while the backyard offers a year-round hot tub, gas line BBQ, and a dry bar for relaxation and entertainment.
Windsor
01/07 – 31/07
SG$282/nighttotal: SG$8460 (30 )
Convenient Family Home In Remington Park
4 5
apartment , Windsor
This detached house in Remington Park, Windsor, offers proximity to cultural sites such as the Fox Theatre and Detroit Masonic Temple, as well as easy access to international crossings including the Detroit Windsor Tunnel, situated 2.7 kilometres away, and the Ambassador Bridge. The property features four bedrooms, accommodating up to eight guests, with a fully equipped kitchen, air conditioning, a private garden with a patio and gazebo, and driveway parking for four cars.
10 1 review
Windsor
28/06 – 31/07
SG$182/nighttotal: SG$6006 (33 )
3bed Family Abode In East Windsor / Tecumseh Rd
3 2
apartment , Windsor
This flat is located in the East Windsor district, offering convenient access to attractions such as Willistead Manor, a 5-minute drive away, and Windsor Riverfront, a 6-minute drive away. This property features a fully equipped kitchen, air conditioning, internet, parking, and a washer/dryer, with a cosy fireplace for added comfort.
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 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.
Destinations nearby
Best Windsor holiday rentals with a balcony
10 3 reviews
Windsor
02/08 – 05/08
SG$328/nighttotal: SG$984 (3 )
Near Midtown & Medical District! Updated Unit
3 2
house , Detroit
This detached house is located near Midtown and the Medical District, offering convenient access to the TCF Centre (5.95 kilometres) and the Motown Historical Museum (a 12-minute walk). The property spans 139 square meters and features three bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher and oven, on-site parking, and complimentary WiFi, accommodating up to eleven guests.
10 1 review
Windsor
17/07 – 19/07
SG$285/nighttotal: SG$570 (2 )
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay For Family
2 2
apartment , Windsor
This city centre flat in Windsor offers prime access, being a short walk to Caesars Casino and the waterfront, with dining and nightlife options also within easy reach. This accommodation sleeps up to 8 guests and features 2 bedrooms, 1 bathroom, a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, and 2 complimentary parking spaces, with a grocery store located directly behind the building.
Windsor
25/07 – 26/07
SG$1609/nightfor 1 night
7br House 19 Ppl Dt Windsor Wd Free Parking
1 4
house , Windsor
Vacation rental. Your accommodation will be based in Windsor. Facilities and services include a kitchen, air conditioning and an iron. This house also has a terrace!
9.5 279 reviews
Windsor
03/10 – 07/10
SG$208/nighttotal: SG$832 (4 )
Downtown Detroit Modern Loft W/free Parking 420
1 2
apartment , Detroit
This one-bedroom apartment is located in Corktown, a historic Detroit neighbourhood, just 1.5km from the Detroit Riverwalk, Huntington Place, and the People Mover. It has excellent user, location, and cleanliness ratings. The apartment offers 93 square metres of space, accommodating up to three guests. It features a fully equipped kitchen, a private balcony, a tennis court, and a spa, as well as free Wi-Fi and a washing machine.
Best Windsor holiday rentals with air conditioning
9.2 560 reviews
Windsor
25/07 – 26/07
SG$116/nightfor 1 night
706# Two-bedroom Apartment Near The Border Tunnel
1 4
apartment , Windsor
This apartment is located in Windsor's nightlife district, just a 3-minute walk from Detroit Riverside Park and 5 minutes from the casino. With an excellent user rating, a very good location rating, and an excellent cleanliness rating, you can be sure of a pleasant stay. The apartment has two bedrooms, a bathroom, and can accommodate up to five guests. You'll have access to a fully equipped kitchen with a fridge and microwave, central air conditioning, a garden, and free on-street parking.
9.3 3 reviews
Windsor
01/07 – 01/01
SG$152/nighttotal: SG$27968 (184 )
Modern 2br/2ba Retreat • 2 Queen Beds With Parking
2 2
apartment , Windsor
This modern two-bedroom flat in Windsor is situated just 500 metres from the Riverfront and Dieppe Gardens, offering convenient access to Caesars Windsor Casino, Devonshire Mall, and the University of Windsor. This serviced apartment accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a fitness centre, and free Wi-Fi, making it ideal for those visiting the Essex County Wineries or Point Pelee National Park.
8.7 14 reviews
Windsor
03/07 – 05/07
SG$106/nighttotal: SG$212 (2 )
Sweet Staycation: Riverside - Ottawa St @ Windsor
2 2
apartment , Windsor
This three-bedroom house is located on Ottawa Street in Windsor, a short walk from local restaurants and cafés, and a few blocks from parks, grocery stores, and the scenic Riverside. This comfortable flat for six guests offers a minimalist interior, air conditioning, internet, a kitchen, and parking, with pets welcome for a convenient short-term stay.
9.5 73 reviews
Windsor
26/09 – 28/09
SG$131/nighttotal: SG$262 (2 )
Affordable 2 Bedroom Apartment
1 2
apartment , Windsor
This Windsor apartment, conveniently located in an unspecified neighbourhood, offers easy access to local amenities and attractions, though precise distances to specific landmarks are not provided. The two-bedroom flat, situated in a basement with 8-foot ceilings, sleeps four guests and includes a fully equipped kitchen, fast Wi-Fi, and parking.
