Holiday rentals in Windsor
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Windsor
Total holiday rentals
Explore 1,540 holiday rentals in Windsor
Nightly prices starting at
Windsor holiday rentals start at $13 SGD per night before taxes and fees
Verified guest reviews
Over 92,160 verified reviews to help you choose
Family-friendly holiday rentals
690 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 410 rentals that welcome pets
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
970 properties have a dedicated workspace
Wifi availability
1,510 of Windsor holiday rentals include wifi 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
Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
5 Star Hotel Inspired Home | Gym • Sauna • Arcades
Come and stay at this 5-star inspired home! Over 3,400 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.
Walkerville Urban Oasis, Exec. King 2BR W/Parking
Keep it simple at this peaceful, centrally located place. Our unit boasts modern furniture, super comfy king size bedroom and another cozy full size bedroom with feather duvet and fluffy pillows also blackout blinds /drapes for a good nights rest. Modern kitchen with stainless steel appliances and washer/dryer, there’s a great dining nook to enjoy a wholesome meal as our kitchen comes fully stalked with anything you might need to cook with . Enjoy our large shower with soft XL bath towels.
Windsor Perfect Stay
Welcome to modern 1BR suite in Windsor’s safest area! Relax in a queen bed, stream on Amazon FireTV, and cook in a sleek kitchen with new appliances. Spa-style bath with glass shower and pebble floor. Pot lights throughout. Free parking for 2 cars, self check-in, and outdoor security cameras. Just 3 mins to Devonshire Mall & Walmart, 2 min walk to Tim Hortons, Gas Station, 10 mins drive to downtown Windsor & close to restaurants & other big shopping centers. Stylish, secure, & super convenient!
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
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.
Modern guest suite downtown
Self contained 1 bedroom suite in the heart of downtown Windsor. This thoughtfully designed space combines both modern comfort and old world charm. Perfect for working professionals, couples or solo travelers. This unit features a separate entrance, stainless steel appliances, an oversized shower, spacious bedroom, a work space, large windows and laundry access. Relax and unwind in the backyard or enjoy the convenience of local shops, cafés, restaurants and vibrant nightlife just steps away.
The Emerald Chandelier Room
Experience living in a modern glamorous emerald green & chandelier themed room hosted by EM Boutique Suites. This spacious 2 bedroom 2 bathroom condo boasts large bedrooms with 2 full bathrooms, full kitchen with an island & stainless steel appliances, full living room & large dining room table. Enjoy a view of Erie st from the unit's private balcony. Our location is surrounded by many restaurants, cafes and boutique shopping right outside our doorstep with Casino & waterfront 5 min drive.
Serene Green 2BR Haven in Little Italy w/ Parking
Welcome to this stylish 2-bedroom unit, thoughtfully designed for families, business travelers, and vacation stays. Enjoy premium hotel-quality beds, a newly renovated kitchen, in-suite laundry, smart TV, electric fireplace, Wi-Fi, free on-site parking for a comfortable stay. This is a main-floor unit in a duplex conveniently located in central Windsor, you're a short walk from Italian restaurants, cafés, and shops, and an easy drive to downtown Windsor, Detroit, and Quellette Hospital.
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.
Modern Walkerville Gem | HotTub & Cozy Backyard
This beautifully renovated townhome combines upscale 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. At night, rest easy on two plush queen size beds and comfy queen pillows.
Windsor Casino and International Swim Meet AirBnb
Complete New Renovation to the whole house: 1st floor has 2 bedrooms, and a massive spacious 2nd floor(700 sqft, 3x other rooms sizes, perfect for meetings, study, full bathroom suite. coming from the US for nightlife. This stylish/unique place is perfect for group trips. Casino, Riverside, Swim Meet, restaurants, easily fit for 2 families(2 TVs). Provide free parking at the Airbnb, then walk 1 minute to the Casino. 5 minutes walk to all the bars and restaurants in Ouellette.
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!
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Stylish Loft w/ River View Balcony in Walkerville.
Trendy Walkerville Distillery Home & Garden
Entire Home in Quiet Area: 3 Bed 2 Bath
Modern 1 BR Granite Counters near Casino & Tunnel
Modern Luxury Home with Patio & Stylish Interior
1 BR Modern Loft Windsor (WEST) by the Bridge
Bright 2 BDRM | Near Casino, Border & UWindsor
The Boho Oasis: Deluxe Apartment
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $102 SGD | $106 SGD | $110 SGD | $112 SGD | $121 SGD | $115 SGD | $112 SGD | $120 SGD | $111 SGD | $111 SGD | $106 SGD | $107 SGD |
| Avg. temp | -3°C | -2°C | 3°C | 9°C | 16°C | 21°C | 23°C | 22°C | 18°C | 12°C | 5°C | 0°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.
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- Point Pelee National Park
- Ford Field
- Little Caesars Arena
- Michigan Stadium
- Comerica Park
- Detroit Zoo
- Mt. Brighton Ski Resort
- University of Michigan Historical Marker
- University of Michigan Museum of Art
- Pine Knob Music Theatre
- University of Windsor
- Maumee Bay State Park
- Motown Museum
- Lake St. Clair Metropark
- Huntington Place
- The Heidelberg Project
- Hollywood Casino at Greektown
- Fox Theatre
- Kensington Metropark
- Wayne State University
- Renaissance Center
- The Ark
- Hart Plaza
- Detroit Historical Museum