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Holiday rentals 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.
Flat in Walkerville
4.95 out of 5 average rating, 300 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, 48 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
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.
Flat in Windsor
4.86 out of 5 average rating, 194 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!

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, 107 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!

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, 133 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
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, 242 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 bright and airy bedroom features a spacious bed dressed in soft linens, complemented by decorative pillows. A large wall clock adds a modern touch. Natural light fills the room through a sliding glass door, while a flat-screen TV is situated on a sleek stand.
Flat in Downtown Windsor
5 out of 5 average rating, 6 reviews

Private Patio, Farmrs Mrkt, 24/7 Gym

Welcome to the luxurious Boutique apartment building, The Bitcoin Building, located in the heart of the city. Enjoy a rejuvenating sleep on our BeautyRest hotel style mattresses, TV with Amazon fire stick with 1000s of channels/Movies. Elegant furniture and soft, warm cork flooring and a ultra Cool fireplace, Patio overlooking Pelissier St, stainless steel appliances and fully stocked kitchen will leave you wanting to stay longer. Includes one free parking space and free access to a 24/7 Gym.

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, 189 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 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
4.89 out of 5 average rating, 19 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, 119 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.
Flat in Walkerville
4.97 out of 5 average rating, 151 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 spacious backyard is presented, showcasing a hot tub situated on a concrete pad. Green grass lines the space, complemented by wooden fencing and ambient lighting. A small tree is visible in the corner, and utility lines are present in the sky against a colorful sunset backdrop.
Home in Walkerville
4.96 out of 5 average rating, 107 reviews

Modern Walkerville Gem | HotTub & Cozy Backyard

This beautifully renovated townhome combines luxury and comfort. Cook in the spacious kitchen with new stainless steel appliances and granite countertops, dine at the custom live-edge wood table, and enjoy your favorite shows on a 65" Roku TV with Sonos soundbar. Relax in the deep bathtub or retreat to the backyard oasis featuring a large deck, hot tub, natural gas BBQ, patio furniture, and beautiful lighting. Rest easy on two plush queen beds in this stunning retreat.

Popular amenities for Windsor holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Windsor's top sights

Little Caesars Arena

311 locals recommend

Ford Field

299 locals recommend

Hart Plaza

106 locals recommend

Detroit Institute of Arts

757 locals recommend

Belle Isle

176 locals recommend

Eastern Market

374 locals recommend

Other great holiday rentals in Windsor

Top guest favourite
A modern kitchen features sleek white cabinets and quartz countertops. Stainless steel appliances are neatly arranged, with barstools positioned at a large island. Natural light streams through multiple windows, highlighting the clean lines and minimalist design of the space.
Private room in South Windsor
4.97 out of 5 average rating, 68 reviews

Near restos, parks, plazas, Walmart, 401

Superhost
Private room in Walkerville
5 out of 5 average rating, 3 reviews

Room 2 - Atlas and Rachel Home

Top guest favourite
A bright living room features deep blue walls with elegant window treatments. A polished wooden table sits at the center, surrounded by light-colored armchairs. A piano is positioned against one wall, while a decorative floral arrangement adds a touch of warmth.
Private room in Windsor
5 out of 5 average rating, 85 reviews

Beautiful and Cozy Deluxe Ensuite

Guest favourite
A modern bedroom features a spacious bed with soft bedding and decorative pillows. A large mirror reflects the light from the window, which is adorned with dark blinds. A stylish desk with an office chair and a lamp complements the room's decor.
Private room in Riverside
5 out of 5 average rating, 5 reviews

Cozy room with dedicated bath!

Guest favourite
Private room in Windsor
5 out of 5 average rating, 9 reviews

Professionals Favorite Place

Guest favourite
The exterior of a two-story brick house is showcased, featuring a stately entrance with double doors and a wide staircase. Well-maintained shrubs and small trees frame the front, while a paved driveway leads up to the entrance. Neutral-colored walls and dark accents complement the inviting facade.
Private room in South Windsor
4.92 out of 5 average rating, 60 reviews

Quiet and comfortable room #2

Guest favourite
A cozy room features a metal bed with a floral-patterned bedspread. Natural light enters through a window dressed with floral curtains. A small table with a glass top is paired with a chair, while a white dresser is positioned nearby, adorned with neatly folded items.
Private room in Downtown Windsor
4.87 out of 5 average rating, 46 reviews

#2 Comfy Room in Downtown near UoW/Tunnel

Superhost
A spacious bedroom features a comfortable bed with a gray and green comforter. A modern desk and chair are positioned against one wall. A flat-screen TV is mounted on another wall, while natural light filters in through a window, enhancing the calming atmosphere.
Private room in Downtown Windsor
4.86 out of 5 average rating, 58 reviews

Cozy Suite with Private bathroom

When is the best time to visit Windsor?

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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 1,570 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    1,530 of Windsor holiday rentals include wifi 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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