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Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of the two-story property features light blue siding and a decorative gabled roof. A covered porch with a white railing and steps leads to the entrance. A wooden gate is visible to the side, providing access to the backyard.
Apartment in Walkerville
4.95 out of 5 average rating, 293 reviews

OLDE WALKERVILLE, Windsor, Ontario

Do you need a nice quite, non-shared clean place to stay ? This cute one bedroom, living room /sleeper sofa, kitchen, full bath (washer/dryer 6 nights + ) Located on the second floor, above our family home, is ready for you to enjoy your stay. In Olde Walkerville, walking distance to restaurants, pubs, boutiques and, the river with walking and bike paths along with summer activities. Short drive to the Casino, Chrysler Theatre / St. Clair Arts, U.S.A Boarder, down town Train Station.

Top Guest favourite
A modern kitchen features light wood cabinetry and a spacious island with seating for four. Pendant lights hang above the counter, illuminating the area. Stainless steel appliances, including a refrigerator and oven, are visible, while the open layout extends into a bright living space with large windows.
Home in South Windsor
5 out of 5 average rating, 44 reviews

Luxury South Windsor Home with Private Gym/Sauna

Come and stay at this 5-star inspired home! Over 3,200 SQ FT Living Space. ✓High-end furniture ✓King Bed w/Beautyrest Harmony Lux Mattress ✓Hotel Collection towels, high thread count sheets ✓Keurig Coffee/Tea Bar ✓ 6 Flatscreen TVs ✓Fully stocked kitchen ✓Gym w/Sauna ✓ 2 Living Rooms Windsor's Best neighbourhood: ✓Highways ✓Airport ✓St. Clair College ✓Mall ✓Fine dining We take pride in keeping the home spotless. Everything is thoroughly cleaned & sanitized to perfection before your arrival.

Superhost
The studio unit features a clean, comfortable queen bed with light-colored bedding. A cozy seating area includes a dark chaise lounge and a wooden table with a chair. The kitchenette displays a sink, stove, and microwave, while large windows provide natural light, framed by sheer and decorative curtains.
Apartment in Downtown Windsor
4.69 out of 5 average rating, 223 reviews

AKSUM- Location! Lovely Studio, Ensuite Shower, AC

We are in Windsor, Canada Enjoy a stylish experience at our centrally located unit of modern elegance and minimalism. Close to many of Windsor's key destinations Aksum is an independent unit with ensuite bathroom (shower) Walk to appointments at City Hall (2min), to the casino or Walkerville or scenic riverfront (5min), Downtown St. Clair and to restaurants You'll be at the Detroit tunnel in 1 min. Bus stop is just outside for easy access to train station and Univ of Windsor No visitors allowed.

Top Guest favourite
A spacious bed is adorned with a floral-patterned comforter in shades of yellow and gray. A small decorative pillow adds a touch of comfort. Natural light filters through two windows, illuminating the cozy seating area nearby, which features a chair with dark stripes.
Guest suite in Riverside
5 out of 5 average rating, 122 reviews

Ray's iNN Olde Riverside (all private)

PRIVATE GUEST SUITE with OWN ENTRANCE. Boutique Hotel Suite inspired,offering amenities,privacy & charm.50”Samsung TV+Netflix.This Suite has a KITCHENETTE with SINK also mini-fridge,microwave,toaster-oven,slow-cooker, cooktop,coffee maker,kettle.PRIVATE BATHROOM with stand up shower.Includes dishes, glassware,utensils, towels,linens,coffee.Seasonal PATIO & lovely landscaping. Within Olde Riverside,close to shops,restaurants,grocery,parks, WFCU Centre.Short walk to a beautiful riverfront & trail.

Guest favourite
A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.
Guest suite in Windsor
4.85 out of 5 average rating, 96 reviews

Private/Quiet Perfect for professionals!

Discover comfort in this private guest suite w/ self-check-in and a separate entrance, located in the tranquil Southwood Lakes neighborhood. Close to golf courses and Devonshire Mall, it’s perfect for relaxation or exploring nearby amenities. Enjoy a swivel mount TV with Netflix and Amazon Prime from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating, ideal for unwinding. Luxury bathroom w/ supplies. Coffee bar! Book your peaceful escape today!

Top Guest favourite
A bright living space is presented with large windows offering stunning lake views. Comfortable seating is arranged around a central coffee table. A dining table for four is positioned nearby, with decorative accents complementing the airy atmosphere. Light floods the room, enhancing its open feel.
Cottage in Essex
5 out of 5 average rating, 236 reviews

The Kiss nTell - Year round - Hot tub - Lake Views

If you “glamp” when you camp, then you’ll appreciate the finer amenities of this boutique style cottage on Lake Erie. Arguably the best views in this tiny cottage community, The Kiss n Tell graces a bluff overlooking the lake - stunning views from every room. Wake to the sound of waves crashing the shore, sunbathe in loungers, dine while the sun glistens on the water, star gaze from the hot tub or sit by a lakeside fire (firewood provided). Endless options w/out leaving this beautiful space.

Guest favourite
A modern living area is featured, furnished with a soft gray sofa and a stylish coffee table. A wooden sideboard is placed against the wall, complemented by decorative items. Light walls enhance the spacious feel, while a chandelier adds subtle brightness to the room.
Home in Walkerville
4.93 out of 5 average rating, 184 reviews

Charming Old Walkerville 2-Bedroom Luxury Suite

Located in the heart of Old Walkerville. Steps from restaurants, bars, shops, parks and the waterfront. A bright and comfortable main level suite that's part of a large duplex home. Perfect for relaxing visitors or working professionals. There are two spacious bedrooms with queen beds, closet and drawer storage. The grand room and kitchen are fully equipped just like home. The deck and yard space are available for fresh air fun and entertainment. There are 2 parking spots on site.

Guest favourite
A living area is presented with a dark, plush sofa and a low coffee table situated on a textured area rug. A round mirror decorates the wall, reflecting light. A doorway leads to a bedroom space, while a small dining area with bar stools is visible to the side.
Apartment in Walkerville
4.93 out of 5 average rating, 107 reviews

Walkerville Loft (Main floor unit)

Welcome to our charming loft nestled in the heart of a Walkerville in Windsor. This thoughtfully designed space combines modern comfort with historical charm. Perfect for couples or solo travelers, our cozy loft features fire place, high ceilings, and large windows. Enjoy the convenience of being centrally located, with iconic landmarks, local shops, and vibrant cafes just steps away. Immerse yourself in the city's rich history during the day and unwind in this stylish retreat at night.

Superhost
A stylish living area features a green velvet sofa complemented by a wooden coffee table with intricate detailing. Large windows are draped with green curtains, allowing natural light to enhance the space. A decorative mirror and a floor lamp add character to the room.
Home in Walkerville
4.91 out of 5 average rating, 11 reviews

Serene Green 2BR Haven in Little Italy

Welcome to this luxurious 2-bedroom home featuring European designer furniture — family-friendly and work-from-home ready. Enjoy 5-star hotel beds, a renovated kitchen with stainless steel appliances, free laundry, Wifi, standing desks, a plush velvet sofa with a 50" TV, and convenient on-street free parking. Centrally located in Windsor, just a 5–10 min walk to Italian dining and shops, with easy access to Windsor downtown, Detroit border, Highway 401, and Windsor Regional Hospital.

Top Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A quartz island is complemented by a decorative tray with coffee essentials. A wall clock adds a touch of functionality, while a bowl of green apples offers a fresh accent.
Home in Windsor
4.99 out of 5 average rating, 113 reviews

Luxurious 3BR, King Bed, Ensuite. Perfect Stay!

Welcome to our 2 year old, modern and bright 3-bedroom, 3-bathroom townhome in East Windsor! Our home features a spacious layout with a clean and contemporary design, making it the perfect spot for your next getaway. The king-sized bed in the master bedroom comes with an ensuite bathroom for added privacy and convenience. Great location, close to WFCU Centre. Perfect for family vacations, weekend getaways, or business trips. Experience the best of East Windsor from our cozy home!

Top Guest favourite
A modern dining area is highlighted by a wooden table accompanied by four blue upholstered chairs. A minimalist aesthetic is enhanced by a potted plant and wall art featuring colorful portraits. Natural light enters through a window covered by a blind.
Apartment in Walkerville
4.97 out of 5 average rating, 147 reviews

"The Modern Loft" in Walkerville / 2Bed - 1 Bath

Enjoy a luxury modern experience in the heart of Old Walkerville. This modern 2 bedroom loft is newly renovated with luxury finishes while keeping century old details. Restaurants, pubs, cafes, retail all within a minute walk from this superb location. Stay here and get a taste of what Old Walkerville has to offer. DISTANCES TO: Casino - 2 minutes Downtown - 2 minutes Hospital - 5 minutes Detroit - 10 minutes Ford Field - 12 minutes Little Ceasers Arena - 12 minutes

Guest favourite
A dining area is featured with a sturdy wooden table surrounded by six chairs. Natural light enters through two windows, illuminating the grey walls. A flat-screen TV is mounted on the wall opposite the table, while a small trash bin and a sleek metal refrigerator are visible in the corner.
Apartment in Windsor
4.79 out of 5 average rating, 29 reviews

Affordable 3 bedroom apartment

Welcome to your perfect getaway in the vibrant West End, just steps away from the university! Our spacious, fully functional three-bedroom apartment is ideal for larger groups and families looking for comfort and convenience. Enjoy a quiet space to relax, with three well-appointed bedrooms designed to ensure a restful night's sleep. Book your stay today and experience the perfect blend of location and comfort, tailored for memorable moments with your loved ones.

Popular amenities for Windsor holiday rentals

When is the best time to visit Windsor?

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Avg. price$143 NZD$145 NZD$152 NZD$152 NZD$164 NZD$156 NZD$159 NZD$166 NZD$163 NZD$163 NZD$157 NZD$152 NZD
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Quick stats about holiday rentals in Windsor

  • Total holiday rentals

    Explore 1,570 holiday rentals in Windsor

  • Verified guest reviews

    Over 85,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    640 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 380 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    910 properties have a dedicated workspace

  • Wi-Fi availability

    1,530 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym and BBQ grill across Windsor rentals

  • 4.7 Average rating

    Windsor stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Windsor's top spots, include Little Caesars Arena, Comerica Park, and Ford Field

Destinations to explore

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  2. Canada
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  5. Windsor