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Windsor, ON, Canada vacation rentals
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Best Vacation rentals and Airbnb offers in Windsor, ON, Canada

Search Vacation Rentals near the Old Town in Windsor, ON, Canada

These central Windsor, ON, Canada vacation rentals make exploring downtown easy on foot. Skip the hassle of transfers and enjoy a convenient city stay.

Ashanti -King Bed-central-a/c-comfortable-full 1br - Windsor, ON, Canada
9.5 201 reviews

Ashanti -King Bed-central-a/c-comfortable-full 1br

apartment, Windsor
This Windsor apartment rental boasts a central location, a five-minute walk from downtown Windsor, Caesars Windsor, and the Detroit Riverfront, with one-minute proximity to the Detroit-Windsor Tunnel.
The one-bedroom, one-bathroom unit sleeps three guests and features a queen-sized bed, free on-site parking, air conditioning, a full kitchen with microwave, fridge, and freezer, and self check-in.
Unique 2-bdr Historic Warehouse Loft With Terrace ! ! ! - Windsor, ON, Canada
9.5 40 reviews

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

apartment, Windsor
The Warehouse apartment in Windsor, Ontario, is conveniently located near Saint Andrew's Hall (1.7 miles), the Music Hall Center (2 miles), and the TCF Center (1.9 miles).
This 1100-square-foot, two-bedroom condo sleeps nine and boasts a terrace with river views, a private patio, a fully equipped kitchen, free Wi-Fi, and access to on-site amenities including a tennis court, playground, and parking.
Gusii- Main Floor, Central Spot, Full 1br Apt, Ac - Windsor, ON, Canada
9.4 93 reviews

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

apartment, Windsor
This Windsor apartment rental is ideally located in downtown Windsor, a five-minute walk from the casino, the Detroit Riverfront, and the Ambassador Bridge.
The main floor unit features one bedroom, one bathroom, and sleeps three guests, offering a full kitchen with a refrigerator, freezer, and microwave, plus air conditioning, parking, and a garden.
Serene Green 2br Haven In Little Italy W/ Parking - Windsor, ON, Canada
9.6 56 reviews

Serene Green 2br Haven In Little Italy W/ Parking

apartment, Windsor
This centrally located Windsor condo offers a 5-10 minute walk to Italian restaurants and shops, with convenient access to downtown Windsor, the Detroit border, Highway 401, and Windsor Regional Hospital.
This luxurious 2-bedroom, 2-bathroom condo accommodates up to 4 guests and features European designer furniture, 5-star hotel beds, a renovated kitchen with stainless steel appliances, central air conditioning, a private fenced backyard, and work-from-home amenities including standing desks and reliable WiFi, with complimentary light breakfast items and self check-in.

Best Windsor, ON, Canada vacation rentals with air conditioning

Spacious Home With King Beds, Backyard Patio & Bbq - Windsor, ON, Canada
No reviews

Spacious Home With King Beds, Backyard Patio & Bbq

apartment, Windsor
This 3-bedroom detached house in East Windsor is located 15 miles from NextStar Energy and Windsor International Airport, and 6 miles from Tecumseh Mall.
This residence accommodates up to 6 guests, featuring a fully equipped kitchen, a large backyard with a patio deck and BBQ grill, and in-home laundry facilities.
The Bachelor Suite At Stanley/kitchenette&backyard - Windsor, ON, Canada
No reviews

The Bachelor Suite At Stanley/kitchenette&backyard

apartment, Windsor
This Windsor lodging is in Remington Park, offering convenient access to Devonshire Mall, downtown Windsor, universities, colleges, the Nexstar battery plant, the airport, VIA Rail station, the riverfront, and U.S. border crossings.
This one-bedroom suite accommodates two guests and features a private side entrance, a well-equipped kitchenette, a King bed, a Futon, a 32-inch LG smart TV, air conditioning, internet, parking, and a patio with a gazebo overlooking a backyard.
Spacious Family Getaway W/ Pool -Sleeps 12 - 2 Tvs - Windsor, ON, Canada
9.9 49 reviews

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

apartment, Windsor
This five-bedroom house is situated in the Riverside neighborhood of Windsor, about 8 miles from Windsor International Airport and close to grocery stores and restaurants. The home boasts a private backyard with an above-ground pool, two living rooms with 55-inch Smart TVs, a fully equipped kitchen, and a basement with a second bathroom, laundry room, and additional sleeping areas.
Cozy Home In Heart Of Windsor - Windsor, ON, Canada
9.6 19 reviews

Cozy Home In Heart Of Windsor

apartment, Windsor
This Windsor home, ideally located in central Windsor near Windsor Castle and Windsor Great Park (exact distances unspecified), offers easy access to shops, restaurants, and public transport.
This four-bedroom, two-bathroom house sleeps eight guests and boasts a fully equipped kitchen, air conditioning, parking, and excellent internet access; enjoy a peaceful stay in this spacious home with a cozy ambiance.

Frequently Asked Questions about vacation rentals in Windsor, ON, Canada

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

    The Windsor International Aquatic Centre is a great spot for kids. They've got a wave pool, water slides, and a lazy river. And the Windsor Public Library is a great place to visit for a rainy day. They've got a lot of cool activities for kids, like story time and craft sessions.
  • What are the best Airbnb and vacation rentals in Windsor, ON, Canada?

    Historic Little Paris: Walk To Lca - Ford - Comerica, 1890's Stone And Brick Garden Loft and Industrial Vibe Loft-king Bed Suite W Private Door are the most popular Airbnb and vacation rentals in Windsor, ON, Canada among travelers.

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

    You'll get the best deals if you book your vacation rental in the off-season, between November and April. The weather's a bit colder then, but you'll find fewer crowds and lower prices.
  • What are the most popular Airbnbs in Windsor, ON, Canada?

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

    The Windsor International Film Festival in November is a big one. It attracts a lot of filmmakers and movie fans. And in July, the Windsor Jazz Festival is a really fun event with live music and lots of food vendors.
  • What are the best vacation rentals with a pool in Windsor, ON, Canada?

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

    You can spend a whole day exploring the Windsor Sculpture Park for free. Another option is to take a walk or bike ride along the Detroit Riverfront. It's a beautiful spot, and it's completely free.
  • What are the best rentals for families and kids in Windsor, ON, Canada?

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

    The Canteen Restaurant is a great spot for traditional Canadian fare. They've got amazing poutine and a really cozy atmosphere. And if you're looking for something a little more upscale, The Colosseum Restaurant is a great option for fine dining.
  • What are the best rentals or Airbnbs with a jacuzzi in Windsor, ON, Canada?

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

    The Riverfront Trail is a beautiful, paved path that runs along the Detroit River. It's perfect for a leisurely walk or bike ride. And for something a little more challenging, the Windsor Sculpture Park has a few nice trails that wind through the woods.
  • Are there pet-friendly attractions in Windsor, Ontàrio, Canadà?

    The Windsor Sculpture Park is very dog-friendly. They've got a few designated areas where dogs are welcome to run around. And many of the parks in Windsor allow dogs on leash.
  • What are the benefits of choosing a vacation rental in Windsor, Ontàrio, Canadà?

    Vacation rentals offer more space and privacy than a hotel. You'll also have access to a kitchen, so you can save money by cooking some of your own meals. Plus, you'll often find that vacation rentals are located in more convenient and interesting neighborhoods.
  • What are the top sports attractions and facilities in Windsor, Ontàrio, Canadà?

    The WFCU Centre is home to the Windsor Spitfires, a junior hockey team. It's a great place to catch a game. And the University of Windsor has a beautiful athletic complex with a swimming pool, gym, and track.

Popular destinations

Choose the Right Vacation Rentals with a Terrace in Windsor, ON, Canada

Start your morning right with a vacation rental in Windsor, ON, Canada featuring a private balcony and stunning views.

Perfect Getaway In Corktown! - Windsor, ON, Canada
9.0 19 reviews

Perfect Getaway In Corktown!

apartment, Detroit
This chic Corktown Detroit townhome is located less than three minutes from Michigan Central Station, Comerica Park, Ford Field, and Little Caesars Arena.
The 1,190-square-foot one-bedroom, two-bathroom unit sleeps three guests and features a fully equipped kitchen, in-unit laundry, a balcony, a spa, parking, and easy access to nearby outdoor activities like kayaking and cycling.
Cozy 4 Bedroom Home Near Tecumseh Mall - Windsor, ON, Canada
No reviews

Cozy 4 Bedroom Home Near Tecumseh Mall

house, Windsor
This four-bedroom house is located in Windsor near Tecumseh Mall, offering proximity to Windsor International Airport, which is 3.1 miles away, and TCF Center, 6.8 miles away.
This 1100 square foot residence accommodates up to 11 guests with four bedrooms, two bathrooms, a fully equipped kitchen, and a fireplace, featuring a private entrance, dining area, outdoor patio, and balcony with free WiFi.
Spacious Cheerful Home With 2 Free Parking - Windsor, ON, Canada
No reviews

Spacious Cheerful Home With 2 Free Parking

cottage, Windsor
This cozy cottage in Bridgeview, Windsor is conveniently located within walking distance of the University of Windsor, the Toldo Lancer Centre, and an Asian Multifood Supermarket. This makes it a great option for families, students, or anyone looking for a convenient and affordable place to stay.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to two guests. It features a fully equipped kitchen, a study room, a basement with an exercise area, a fenced backyard with a double deck balcony, and two off-street parking spaces.
Spacious 3-bedroom Apartment On East Jefferson Near Downtown - Windsor, ON, Canada
10 1 review

Spacious 3-bedroom Apartment On East Jefferson Near Downtown

apartment, Detroit
This Detroit East Village rental is located 4 miles from the Detroit Riverwalk, 7 miles from Lake St. Clair, 5 miles from Pewabic Pottery, and 7 miles from Belle Isle Aquarium.
This 3-bedroom, 1-bathroom apartment accommodates up to 6 guests and includes Wi-Fi, air conditioning, a sunroom, and on-site parking.

Compare Vacation Rentals for Families in Windsor, ON, Canada

The right family vacation rental in Windsor, ON, Canada makes all the difference, keeping you close to top city attractions.

Modern 2br  Gated Parking  10 Min To Downtown - Windsor, ON, Canada
No reviews

Modern 2br Gated Parking 10 Min To Downtown

apartment, Detroit
This renovated duplex apartment in Detroit is located approximately 10 minutes from Downtown, offering convenient access to cultural sites like the Fox Theatre and Henry Ford Museum.
This family-friendly rental features 2 bedrooms, 1 bathroom, a fully equipped kitchen with a fridge and microwave, in-unit laundry, high-speed internet, air conditioning, a private entrance, and a balcony, with free gated parking and smart TVs for entertainment.
Luxury 1 Bedroom, 1 Bath Apt. In The Middle Of Downtown Detroit W/parking Spot! - Windsor, ON, Canada
9.0 12 reviews

Luxury 1 Bedroom, 1 Bath Apt. In The Middle Of Downtown Detroit W/parking Spot!

apartment, Detroit
This Downtown Detroit vacation rental is ideally located within walking distance of Campus Martius Park and Greektown Casino, offering easy access to major attractions and public transportation.
The one-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen, in-unit laundry, a smart TV, and on-site parking; enjoy nearby dining and entertainment options.
Lumber Barons Brush Park Penthouse - 3br - 2 Kings/queen/2.5bath - 1-car Garage - Windsor, ON, Canada
10 41 reviews

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

apartment, Detroit
This apartment is located in Detroit's Brush Park neighborhood, a short walk from the Detroit Institute of Arts, Comerica Park, Little Caesars Arena, and the Fox Theater. It's an excellent choice for travelers looking to explore Detroit's vibrant arts and culture scene.
The apartment is spacious and can comfortably accommodate up to 6 guests. It has all the amenities you need for a comfortable stay, including a fully equipped kitchen, multiple TVs with streaming services, and a private terrace.
Family-sized 3br  5 Beds  Near Downtown - Windsor, ON, Canada
9.8 146 reviews

Family-sized 3br 5 Beds Near Downtown

apartment, Windsor
This 3-bedroom house is located in a quiet residential area just outside downtown Windsor, a short walk from the waterfront and a quick drive to the Detroit-Windsor Tunnel. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This family-friendly home comfortably sleeps 8 guests with its 3 bedrooms and 1 bathroom, offering a dedicated kids' space in the basement. The house is equipped with a fully equipped kitchen, laundry facilities, a spacious backyard with a BBQ grill, and ample parking for up to three cars, making it perfect for families and groups looking for a comfortable and convenient stay.

Best Windsor, ON, Canada vacation rentals with parking

Chic Getaway | 1br Suite W/ Parking & Ac - Windsor, ON, Canada
9.2 12 reviews

Chic Getaway | 1br Suite W/ Parking & Ac

apartment, Windsor
Spa Retreat, Suana, Free Massages, Rooftop Deck! - Windsor, ON, Canada
9.9 27 reviews

Spa Retreat, Suana, Free Massages, Rooftop Deck!

apartment, Windsor
Elegant Private Suite | Spacious Walkout Retreat - Windsor, ON, Canada
9.6 9 reviews

Elegant Private Suite | Spacious Walkout Retreat

apartment, Windsor
Art Loft Luxury Apartmentartist's Home - Windsor, ON, Canada
10 46 reviews

Art Loft Luxury Apartmentartist's Home

apartment, Windsor

Find the Best Luxury Vacation Rentals in Windsor, ON, Canada

Discover high-end comfort in Windsor, ON, Canada with upscale rentals that prioritize luxury and guest satisfaction.

Executive 2br Lower Suite Private & Spacious Close To Usa Border - Windsor, ON, Canada
9.9 13 reviews

Executive 2br Lower Suite Private & Spacious Close To Usa Border

apartment, Windsor

Discover Pet-Friendly Vacation Rentals in Windsor, ON, Canada

Experience a pet-friendly stay in Windsor, ON, Canada with vacation rentals located steps away from city dog parks and walking trails.

Stylish Chic Retreat At Lafayette Lofts Apts - Windsor, ON, Canada
No reviews

Stylish Chic Retreat At Lafayette Lofts Apts

apartment, Detroit
Bridge To Adventure 2 Beds To Relax - Windsor, ON, Canada
10 12 reviews

Bridge To Adventure 2 Beds To Relax

apartment, Windsor
Pet Friendly Apartment 1bd In Arena District With Event Parking - Windsor, ON, Canada
8.6 8 reviews

Pet Friendly Apartment 1bd In Arena District With Event Parking

apartment, Detroit
Roof Top 2-bedroom Penthouse ! ! ! - Windsor, ON, Canada
9.5 100 reviews

Roof Top 2-bedroom Penthouse ! ! !

apartment, Windsor

Top-Rated Vacation Rentals with a Pool in Windsor, ON, Canada

A Windsor, ON, Canada vacation rental with a pool ensures a refreshing swim in the heart of the city is always an option.

The River Condos - Windsor, ON, Canada
No reviews

The River Condos

apartment, Detroit
Windsor Luxury Oasis - Windsor, ON, Canada
10 4 reviews

Windsor Luxury Oasis

house, Windsor
Cozy 1-bedroom Apartment Heart Of Downtown Detroit - Windsor, ON, Canada
No reviews

Cozy 1-bedroom Apartment Heart Of Downtown Detroit

apartment, Detroit
Modern Spacious 1 Bedroom And A Den Home (Lower Unit) - Windsor, ON, Canada
8.6 7 reviews

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

apartment, Windsor

Top Vacation Rentals with a Hot Tub in Windsor, ON, Canada

Coming home to a private hot tub after a day of urban exploration completely transforms your Windsor, ON, Canada experience.

The Victorian On Victoria - Windsor, ON, Canada
9.8 27 reviews

The Victorian On Victoria

apartment, Windsor
Lux. Modern Blue Heron Home Fireplace, Garage, Pet-friendly, Easily Accessible! - Windsor, ON, Canada
9.4 3 reviews

Lux. Modern Blue Heron Home Fireplace, Garage, Pet-friendly, Easily Accessible!

apartment, Windsor
Modern Walkerville Gem | Hottub & Cozy Backyard - Windsor, ON, Canada
9.9 146 reviews

Modern Walkerville Gem | Hottub & Cozy Backyard

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

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

apartment, Detroit
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