Vacation Rentals By Owner In Windsor, ON

Find your sanctuary at Little River Retreat. Bordering parks, with luxe vibes, a crackling fireplace, and a dreamy hot tub. Enjoy a walk or bike ride through beautiful parks and beaches, including the 10 km+ Ganatchio Trail and Sandpoint Beach (both 5 minutes away). In under 45 min, find yourself in wine country, or for nature lovers, Point Pelee National Park. WFCU Centre 3 min away. Caesars Windsor, tunnel & bridge to USA 10-15 min away. Detroit airport approx 45 min, new battery plant 9 minbrbrThe spacebrOpen the front gate to find a delightful little courtyard awaiting you, complete with a sizzling BBQ, a comfortable patio set, and a dreamy hot tub. Open the front door and you will find yourself in our cozy, open-concept living room, dining room, and kitchen (overlooking a view of the park). Steps away, you can access your relaxing bedroom and a fully-equipped bathroom.brbrGuest accessbrAll parts of the space within Unit B’s property are available for use by our guests, with the exception of the locked storage room next to the kitchen (which is used by our cleaning staff). Any outdoor spaces belonging to the other units on the property are inhabited by other tenants and are not for use by guests.

Perfect hideaway with a hot tub and a fireplace

Windsor, Ontario, Canada

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$224.53

Welcome to our modern private basement suite with a private entrance! Featuring 3 bedrooms (1 king, 2 queen, 1 twin), 1.5 baths, and sleek marble floors. Enjoy a fully equipped kitchen with amenities like a kettle, air fryer, and stainless steel cutlery etc. Relax in the spacious living area with a fireplace and a 58-inch TV. Laundry facilities and fast Wi-Fi are provided. Ample natural light streams in through many windows. There's an office space and a sofa bed accommodating two more guests.brbrThe spacebrStep inside to discover a welcoming living space providing the perfect backdrop for your getaway. You'll feel right at home in our thoughtfully curated space.brbrThe kitchen is fully equipped with top-of-the-line appliances and ample counter space.brbrRetreat to one of our three beautifully appointed bedrooms at the end of the day. The first room features a cozy twin bed, ideal for solo travellers or children, while the other two bedrooms boast luxurious queen and king-sized beds with premium linens for a restful night's sleep.brbrFreshen up in the pristine full bathroom, complete with a sparkling shower or make use of the convenient half bathroom.brbrWe've thought of everything to ensure your stay is as comfortable as possible. Each bedroom is stocked with comfy bedding and ample closet space, while thoughtful touches like bedside lamps and blackout curtains add an extra layer of convenience.brbrGuest accessbrExperience complete autonomy with your own dedicated entrance, conveniently located in the backyard. This separate entrance ensures that your stay is entirely private, allowing you to come and go as you please without disturbance.brbrOther things to notebrPlease note our policies: pets are not allowed. We enforce a zero-tolerance policy for partying or indoor smoking, with fines for violations. Noise bylaws start at 10 pm; please keep outdoor activities indoors. Kindly refrain from wearing outdoor shoes inside. A cleaning fee applies.

Modern Private Basement Suite

Windsor, Ontario, Canada

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Exceptional(3)

$151.62

Quiet 3BR Home in South Windsor – Near Hwy 401 & EC RowbrbrRelax and enjoy this clean, quiet, and fully private home — perfect for families, professionals, or travelers looking for comfort and convenience. br House Rulesbrbr✅ Check-in: 3:00 PMbr✅ Check-out: 11:00 AMbr✅ Maximum guests: 5br No smoking insidebr No pets allowed (unless approved in advance)br No parties or eventsbr Quiet hours: 10:00 PM – 8:00 AMbr Please treat the home with respect – clean up after yourself and report any damagesbr Laundry: Please use washer/dryer responsiblybr Lost keys may result in a replacement feebr All guests must be registered before check-in – No unregistered overnight guests allowedbrbrWe want everyone to enjoy their stay while keeping the home safe and peaceful. Thank you for your understanding and cooperation!brbr Entire House | 3 Bedrooms | 2 Bathroomsbr Private Garage + Driveway Parkingbr Peaceful Backyard with Comfortable Outdoor Seatingbr Wi-Fi | ️ Fully Equipped Kitchen | Washer & DryerbrbrLocated in a safe and quiet neighborhood in South Windsor, just minutes from Highway 401 and EC Row Expressway — with easy access to downtown, shopping, restaurants, and public transit. Sleeps up to 5 guests max. Perfect for families or business stays.

Perfect 3 bedroom house in prime location of South Windsor. max 5 guests

Windsor, Ontario, Canada

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$121.47

Modern two-bedroom, one-bath apartment in a prime Windsor location. brSteps from scenic riverfront parks and trails, and just minutes to the University of Windsor, Caesars Windsor, and downtown’s shops and dining.brbrConvenient access to the Detroit-Windsor Tunnel and Highway 401 ensures seamless connectivity. St. Clair College, Windsor International Airport, and major employers like the Ford Windsor Engine Plant are all nearby—ideal for professionals seeking comfort and convenience.

Bright & Spacious 2BR Near Downtown Windsor

Windsor, Ontario, Canada

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Cozy place

Windsor, Ontario, Canada

Cozy and clean basement for rent by night or months, washer and dryer available , AC,Heat, fully renovate, you can enjoy your coffee at the patio outside, coffee machine available, your very welcome to stay at anytime.

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$92.01

Discover a rustic-modern 1BR basement suite designed for comfort, style, and relaxation. Perfect for families, city explorers, and weekend getaways, this private retreat featuresbrbrA fully equipped kitchen, fast Wi-Fi, dedicated workspace, and a relaxing porch brbr Just 350m from Wyandotte St. E, enjoy local dining, shops, and vibrant neighborhood spots. brbrBook today for a memorable stay in East Windsor! DM us for the exact address and full details

Cozy Windsor Retreat Near Downtown & Attractions!

Windsor, Ontario, Canada

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$257.39

Welcome to your East Windsor retreat! This spacious rustic-modern home combines a charming 3BR main house with a private 1BR basement suite, perfect for families and groups.brbrEnjoy comfortable bedrooms, a fully equipped kitchen, modern bathrooms, high-speed WiFi, Smart TV, and dedicated workspaces brbrLocal dining, cafés, and shops just minutes away ☕ ️brbrA perfect blend of comfort, space, and convenience for your Windsor stay. Book today for a memorable getaway! DM us for full details

Windsor 4BR Family Home – Parking & Backyard!

Windsor, Ontario, Canada

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$381.14

Enjoy a luxurious stay in this newly renovated two-story home featuring 4 spacious bedrooms, including a private king suite with a spa-style bathroom, jacuzzi, and massage shower. Soaring ceilings and 27 windows fill the open living space with natural light, while silver-plated chandeliers add elegance. Perfect for guests seeking comfort, privacy, and a truly unforgettable experience

Elegant 4BR Retreat + Jacuzzi

Windsor, Ontario, Canada

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$160.68

Summary:brbrYour oasis in the city. Discover Windsor's only SPA apartment, tucked on a quiet street. Step inside and melt into relaxation with a private infrared sauna, soothing rain shower, full body- zero gravity massage chair and red light therapy. Calming decor, air purifiers and endless IPTV channels create a haven of comfort. Unwind on the spacious 800 sqft shared rooftop deck, then wander to the farmers market, riverfront, casino and top restaurants just steps away.brbrbrbrThe Space:brbrLocated on Windsor's nicest downtown street at 445 Pelissier St, you are in the centre of it all with clubs, bars, restaurants, the Riverfront and Caesars Casino just steps away!brbrbrbrGuest Access:brbrYou park at your complimentary and designated parking spot located right behind the building, which you can over look from the windows of the Spa Apartment. brbrbrbrAccess to the building and Suite is fully electronic and contactless. brbrbrbrAnd you have full access to the gorgeous rooftop patio that you can access via the staircase from our private walkway that stretches from the parking at the back of the building to Pelissier St.

Relaxing spa retreat in downtown Windsor

Windsor, Ontario, Canada

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$207.13

Welcome to your East Windsor Farmhouse Escape! This charming 3BR rustic-modern home is designed for comfort and relaxation. Perfect for families, friends, or business travelers, this retreat features. brbrStay connected with high-speed WiFi and Smart TV, and unwind on the cozy porch. Just minutes from shops, cafés, and local spots, enjoy a convenient and comfortable stay.brbrBook today for your East Windsor getaway! DM us for the exact address and full details

Heart of Windsor 3BR Home – Luxury & Comfort!

Windsor, Ontario, Canada

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Exceptional(18)

$90.19

Are you traveling to the University of Windsor or the College, making a pit stop to or from the US, or a couple on a romantic gate away - this place is the perfect rare find. brbr- Access to the beach and riverside trailbr- Stylish modern living areabr- Balcony over looks the Beach. br- King size bed br- Extra air mattress br- Ensuite laundry br- Fully equipped kitchenbr- 2 minutes to the University of Windsor, 2 minutes to the Ambassador Bridge, 5 minutes to DT Windsorbr- Go fishing right by the homebr- Guest Security using ring video door bell.

Condo

Access to the beach and riverside trail.

Windsor, Ontario, Canada

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The charm and aesthetic of county living right in South Windsor

Windsor, Ontario, Canada

Welcome to 2380 Cabana, the charm and aesthetic of county living right in the highly desirable neighbourhood of South Windsor. Not only is this property situated on a large private lot next to a wooded protected area, giving you pure privacy and seclusion. The interior is just as charming as the exterior, on the main floor you are greeted with arched hallways, with original plaster construction, a spacious living room filled with plenty of natural light with newer windows all throughout, an upgraded kitchen with farmhouse sink and newer appliances, 4pc bath, and foyer with exceptional marble stone with access to your 1.5 car garage, with newer sliding glass doors opening up to your fenced backyard, one of many green spaces. The second floor is entirely designed as your primary suite, with a large walk in closet and 2 pc bath that encompasses a private oasis. Situated in a private cut-de-sac this is a perfect home in South Windsor and ideal if you enjoy outdoor space.

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$86.95

Stay at Four Points by Sheraton Windsor Downtown in the heart of downtown. Walk to Caesars Windsor, the scenic riverfront, restaurants, and nightlife. Spacious rooms feature plush bedding, free WiFi, and large workspaces, with select rooms offering Detroit skyline views. Enjoy convenient on-site dining and easy access to the Detroit–Windsor Tunnel—perfect for business trips, weekend getaways, or family stays.

Hotel

Downtown Windsor Stay | Comfort & Convenience

Windsor, Ontario, Canada

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Exceptional(9)

$174.48

Bring the whole family and friends to this great place with lots of room for fun.brbrGreat for short vacations, work from home, and short turnarounds.brbrCan park 6 cars.brbrFridge, stove, dishwasher, coffeemaker, toaster, dishes and cutlery, washer, dryer are available.brbrTesla charger is available.brbrCan host up to 10 people.brbrOur listed price is based on up to four guests. Each additional guest is $60. Guests must provide the accurate number of occupants when booking so we can prepare proper bedding.

Spacious 5BR House, Sleeps 10, Tesla Charger, 6 Parking, Pet Friendly

Windsor, Ontario, Canada

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$327.72

Welcome to our tranquil waterfront retreat, where the soothing rhythm of the water meets the comfort of a well-appointed home. Nestled on the shores of Lake Erie, this stunning residence offers the perfect blend of relaxation, space, and luxury. With its generous number of bedrooms and breathtaking views, it's an ideal destination for families, friends, or groups seeking an unforgettable getaway.

Waterfront Retreat: 6BR Home, BBQ, Sleeps 10

Windsor, Ontario, Canada

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Most popular vacation rentals in Windsor

$118.78

Navy gold dream - 2 bedroom house w/ work station

Windsor, Ontario, Canada

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$164.02

Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

Windsor, Ontario, Canada

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$157.85

Condo

Luxury Condo Windsor/LaSalle Ontario

Windsor, Ontario, Canada

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$143.46

Comfy dream • 2 beds • Netflix • fast wifi

Windsor, Ontario, Canada

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$140.76

Bright & colorful downtown gem with free parking

Windsor, Ontario, Canada

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$140.53

Full House 3 bedrooms 2Washrooms

Windsor, Ontario, Canada

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$134.69

Bed & breakfast

Two Bedroom Luxury apartment in Walkerville.

Windsor, Ontario, Canada

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$134.14

3BR Modern New Home By the Ambassador Bridge & Gordie Howe International Bridge.

Windsor, Ontario, Canada

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$130.64

Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.

Windsor, Ontario, Canada

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$104.35