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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, 303 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.

Guest favourite
A spacious living area features a comfortable gray sectional sofa adorned with decorative cushions. A wooden coffee table is centered on a soft area rug, while a wall-mounted television and a small dining table for two are visible. Natural light enters through large windows.
Apartment in Windsor
4.87 out of 5 average rating, 206 reviews

The Ambassador’s Stay • Bright 1BR Family Retreat

Luxurious 1BR Retreat Prime Location, Perfect for Your Getaway! Escape to this stunning one-bedroom haven in LaSalle, where comfort and convenience meet! Whether you're here for a romantic getaway, a solo retreat, or a business trip, this modern sanctuary has everything you need for a perfect stay. Whether you're here for business or leisure, this luxurious one-bedroom retreat is the perfect home base for your LaSalle getaway. Book now and experience all the comfort and convenience you deserve!

Top Guest favourite
A private outdoor patio features a hot tub surrounded by wooden fencing and a pergola. Comfortable seating is provided by two chairs, with a BBQ grill situated nearby. Natural light filters in through the overhead structure, enhancing the relaxing atmosphere.
Home in Riverside
4.97 out of 5 average rating, 147 reviews

Perfect hideaway with a hot tub and a fireplace

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 min

Top Guest favourite
An outdoor dining area is set with a red table and chairs under a retractable awning. The grey exterior of the lodge is framed by a manicured lawn and wooden fencing, creating a secluded and private atmosphere. Natural light enhances the inviting space.
Home in South Windsor
4.94 out of 5 average rating, 125 reviews

Luxury 2BR home with high ceilings and BBQ w/patio

Labelle Lodge invites you to this bright home with 2 spacious bedrooms and a living area with high ceilings and tons of natural light. Nestled amongst majestic trees, the serene getaway is just 7 minutes away from the US border. Conveniently located near EC Row, you’re minutes away from the Riverside and the entertainment district. Enjoy high speed internet and two smart TVs with all your streaming apps. Indulge in the outdoor dining area and experience the tranquility of South Windsor.

Guest favourite
A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.
Cottage in Lakeshore
4.94 out of 5 average rating, 159 reviews

Waterfront Luxurious Cottage in Lakeshore, Ontario

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

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, 111 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.

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
4.94 out of 5 average rating, 193 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.

Superhost
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
4.82 out of 5 average rating, 119 reviews

Private unit for professionals! Seperate access

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 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
The entrance features a pair of glass-paneled doors surrounded by natural stone walls, illuminated by warm lighting. A wooden staircase is visible beyond the doors, leading to the upper level, with a welcome mat positioned in front.
Guest suite in Riverside
4.98 out of 5 average rating, 224 reviews

Glenn & Deb’s Place

1100 sq. ft guest suite attached to main residence but completely separate space on quiet residential street. Upper level with two bedrooms, washer/dryer and 1 bathroom with custom shower. Lower level has full kitchen, living room with gas fireplace, 42'' television and high speed internet. Independent heating and cooling. Owners are on site for quick response to all your needs. Close to WFCU, Caesars Windsor and all major arteries. We regret we are unable to accommodate pets.

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, 154 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

Top Guest favourite
A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.
Guest suite in Windsor
4.93 out of 5 average rating, 420 reviews

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

Guest favourite
A cozy living area features a light-colored sectional sofa adorned with patterned pillows. A modern glass coffee table sits in the center, complemented by a decorative plant on the side. Exposed brick walls add texture, while a window with an arch design enhances natural light.
Townhouse in Walkerville
4.95 out of 5 average rating, 103 reviews

Cozy Downtown Walkerville Home

Welcome to your perfect home away from home in the heart of Windsor! This charming and cozy residence offers the perfect blend of comfort, style and convenience making it an ideal spot for both short and long stays. Whether you're in town for business, leisure, or a family visit, you'll find everything you need to feel right at home. Situated downtown Windsor just minutes from the VIA train station, Casino Windsor, Detroit tunnel and great popular restaurants

Popular amenities for Windsor holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Windsor's top sights

Little Caesars Arena

319 locals recommend

Ford Field

307 locals recommend

Hart Plaza

108 locals recommend

Detroit Institute of Arts

768 locals recommend

Belle Isle

188 locals recommend

Eastern Market

382 locals recommend

Other great holiday rentals in Windsor

Guest favourite
A cozy living area features comfortable seating with dark leather chairs and a sectional sofa. A glass dining table is set for four, with a view of a television and a doorway leading to a bedroom in the background, complemented by soft wall colors.
Home in Walkerville
4.82 out of 5 average rating, 44 reviews

Paradise Home - Home Away From Home

Superhost
The exterior of a modern, two-story house is displayed, featuring a well-manicured lawn and a charming entryway with decorative details. The pathway is flanked by soft landscape lighting, and neighboring houses can be seen in the background.
Apartment in Downtown Windsor
4.77 out of 5 average rating, 145 reviews

luxury 2-Bedroom Apartment In Downtown Windsor

Top Guest favourite
Guest suite in Downtown Windsor
4.99 out of 5 average rating, 83 reviews

Modern guest suite downtown

Top Guest favourite
A modern dining area is highlighted by a glass tabletop, showcasing a sleek vase filled with fresh herbs. Exposed brick walls provide a warm contrast to the contemporary kitchen visible in the background, featuring white cabinetry and a stylish clock on the wall.
Home in Walkerville
4.9 out of 5 average rating, 59 reviews

Trendy Home Spacious Backyard Historic Walkerville

Guest favourite
The exterior of a modern two-story home is illuminated at dusk, showcasing a welcoming terrace area with stairs leading to the entrance. The building features a mix of wood and metal elements, surrounded by landscaped areas and a spacious driveway.
Home in Belle River
5 out of 5 average rating, 18 reviews

Key West Cottage

Superhost
A modern living area features a plush orange sofa facing a wall-mounted television. Natural light enters through large windows, which are framed by light grey curtains. A neutral-toned area rug lies beneath a coffee table, enhancing the spacious feel of the room.
Apartment in Windsor
4.81 out of 5 average rating, 74 reviews

Rare find by the Riverside

Guest favourite
A bright living area features a tufted sofa, accompanied by a glass coffee table atop a plush area rug. A small dining table is positioned nearby, with four chairs around it. Soft lighting is provided by a lamp beside the seating area, enhancing the inviting space.
Apartment in Walkerville
5 out of 5 average rating, 13 reviews

Modern Walkerville Unit - Steps from Riverfront!

Superhost
The kitchen and dining area feature modern appliances and a dining table with four chairs. Natural light fills the space through large windows, illuminating the light blue walls. A decorative plant sits on the table, complementing the cozy atmosphere.
Home in Remington Park
4.81 out of 5 average rating, 70 reviews

3 bdr upper, prime location

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$136 NZD$137 NZD$144 NZD$144 NZD$155 NZD$147 NZD$144 NZD$154 NZD$142 NZD$142 NZD$136 NZD$137 NZD
Avg. temp-3°C-2°C3°C9°C16°C21°C23°C22°C18°C12°C5°C0°C

Frequently Asked Questions

  • What are the best places to stay in Windsor?

    Windsor has a mix of centrally located neighborhoods near the waterfront, Walkerville for its historic vibe, and Riverside for quieter stays close to parks. Consider areas around downtown if you enjoy easy access to restaurants and cultural sites.

  • What are the best things to do in Windsor with kids?

    Windsor has hands-on exhibits at the Chimczuk Museum, outdoor artwork along the Windsor Sculpture Park, and green spaces for picnics or play along the riverfront. Families also spend time exploring local playgrounds and community events throughout the year.

  • What are some of the best things to do in Windsor?

    Explore the Windsor Sculpture Park, stroll the scenic waterfront, and experience the art galleries around downtown. The city also has historical sites rooted in diverse communities and vibrant food markets.

  • How is the weather in Windsor?

    Windsor has cold winters with temperatures from 19–37°F (-7–3°C), and warm summers ranging 63–84°F (17–29°C). Spring and autumn bring milder weather; packing a mix of layers and a rain jacket is often suggested.

  • When is the best time to visit Windsor?

    Late spring through early autumn is often recommended for comfortable temperatures and outdoor festivals. Visitors frequently enjoy riverfront activities and gardens during these months.

  • What are the best places to visit in Windsor?

    Many explore the Windsor Sculpture Park, Jackson Park's seasonal gardens, and the Art Gallery of Windsor. History enthusiasts may appreciate heritage sites in Walkerville and the local museum.

  • What are some hiking trails in Windsor?

    Windsor has nature trails in Ojibway Prairie Complex, scenic riverfront paths, and wooded routes through Malden Park. These are frequently suggested for walking, birdwatching, and enjoying local plants.

  • What are some family activities we can do in Windsor?

    Families in Windsor explore interactive displays at the Chimczuk Museum, stroll through the Windsor Sculpture Park, and gather at riverside parks for outdoor fun. Seasonal community events and local markets also welcome visitors of all ages.

  • What are some of the best day trip ideas from Windsor?

    Consider exploring Point Pelee National Park for nature walks, venturing to local wineries for tastings, or visiting neighboring towns with distinct cultural and culinary experiences. Outdoor enthusiasts also enjoy regional conservation areas and sandy beaches around the region.

  • Are there any pet friendly accommodations available in Windsor?

    Many Windsor vacation rentals and stays are pet-friendly, especially in neighborhoods like Riverside, Walkerville, and near green spaces. Check specific listings for details, as rules may vary by property.

  • What are some local tips for visiting Windsor?

    Locals suggest strolling the waterfront trail at sunset, exploring historic Walkerville for its cafes and shops, and sampling locally made pastries. Packing comfortable walking shoes is helpful, as many highlights are best on foot.

  • What is Windsor known for?

    Windsor is known for its multicultural heritage, automotive history, and vibrant riverfront stretching along the Detroit River. The city has a strong connection to Canadian whisky traditions and is often recognized for its public art installations.

  • What are the best hidden gems to explore in Windsor?

    Seek out street art and indie shops in Ford City, local bakeries with longstanding recipes, and small heritage museums tucked into neighborhood corners. Ojibway Prairie Complex is often recommended for those interested in native plants and quiet walking trails.

  • What are the best foods to try in Windsor?

    Windsor is frequently suggested for its locally made pizza known for signature shredded pepperoni, Lebanese grilled dishes, and classic Canadian butter tarts. Polish, Italian, and Middle Eastern bakeries also feature beloved pastries and breads.

  • What should I bring for a trip to Windsor?

    Pack layers to suit changing seasons, a rain jacket, and comfortable shoes for exploring parks and city strolls. Bringing a reusable water bottle and sun protection is often handy if you plan to spend time outdoors.

  • What is the nightlife in Windsor like?

    Windsor's nightlife has a variety of laid-back pubs, music venues, and cocktail bars, especially around downtown and Ouellette Avenue. Some neighborhoods also have lounges with live bands and dance floors for a mix of experiences.

  • What are the most popular events or festivals in Windsor?

    Windsor hosts a popular summer waterfront fireworks display, the Windsor International Film Festival in autumn, and seasonal multicultural festivals celebrating local communities. Outdoor concerts and food events are frequently suggested during warmer months.

  • Are there family friendly vacation rentals in Windsor?

    Many Windsor vacation rentals are suited to families, with larger spaces available near parks or in Walkerville and Riverside neighborhoods. Check for listings with amenities like kitchens and extra bedrooms for added comfort.

Quick stats about holiday rentals in Windsor

  • Total holiday rentals

    Explore 1,660 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 88,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    690 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 420 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    990 properties have a dedicated workspace

  • Wi-Fi availability

    1,610 of Windsor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace 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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