Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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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.
Walkerville Charm Home
This stunning 4 bedroom, 6 bed home is dressed to impress! We have spared no detail to ensure your comfort, including: *4 Casper queen beds; * 2 Casper full beds; * a Weber gas BBQ; * lightning fast WIFI connection; * a 50-inch smart Samsung TV in the living room; * a 55-inch smart Samsung TV on the upper floor; * a large formal dining room; * an open concept dining/living/sitting space which can comfortably seat 10 people; * a kids' korner for playtime; * and+++ *Note: Hot tub not available
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.
Serene Green 2BR Haven in Little Italy w/ Parking
Welcome to this luxurious 2-bedroom unit featuring European designer furniture — family-friendly and work-from-home ready. Enjoy hotel-quality beds, a newly renovated kitchen with stainless steel appliances, complimentary laundry and Wi-Fi, a plush velvet sofa, a 50" TV, and free on-site parking. Centrally located in Windsor, just a 5min walk to Italian dining and shops, with easy access to downtown, Detroit border, and Windsor Regional Hospital. This is the main-floor unit of a duplex.
Couple's Romantic Retreat with hot tub, fire pit.
Romantic & soothing discreet hideaway. Relax, reunite & enjoy the night. Complementary Bathrobe for Sunday to Thursday bookings. 1 for return guests. -private backyard Oasis with Hot tub, Gazebo, outdoor Tv, accent lighting, BBQ and fire pit. -king size bed; -couple's spa shower; -massage table -fully stocked chef's kitchen; -private garage parking; -nearby parks and trails; -plus all of the comforts of being in the city. Everything you need to enjoy a restful and relaxing weekend away.
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.
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!
Architectural Gem | Direct-Entry Pool
Welcome to Windsor’s hidden gem. This modern 2-bedroom retreat features a sunken living room, soaring patio doors, and a heated pool steps away. The pool is open year-round at 70°F; warmer settings available for an additional cost. The main floor offers an open layout with a sleek kitchen and tree-top terrace. Upstairs, unwind in a spa-inspired bedroom with a soaker tub, rainfall shower, and rooftop retreat. Two private terraces and unforgettable design, complete the experience.
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
Walkerville Loft - Exclusive Main floor unit
Welcome to our charming main floor private loft in the heart of a Walkerville, Windsor. This space combines modern comfort with some abstract 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 cafes just steps away. Enjoy the city's historic areas during the day and unwind in the unique loft at night.
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor
Clean 4 BR Home with Karaoke and Arcades
Serenity Waterside Retreat!
Modern guest suite downtown
Walkerville Urban Oasis, Exec. King 2BR W/Parking
Cozy, Modern 2BR w/ Remote Workspace, Patio & Gym
The Boho Oasis: Deluxe Apartment
The Walkerville Hidden Gem · Distillery District
Executive 2BR Lower Suite · Private & Spacious
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £59 | £61 | £63 | £65 | £70 | £66 | £65 | £69 | £64 | £64 | £61 | £62 |
| 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.
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 £7 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
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- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Michigan Stadium
- Comerica Park
- Detroit Zoo
- Mt. Brighton Ski Resort
- University of Michigan Museum of Art
- University of Michigan Historical Marker
- Motown Museum
- University of Windsor
- Maumee Bay State Park
- Hollywood Casino at Greektown
- The Heidelberg Project
- Lake St. Clair Metropark
- Kensington Metropark
- Fox Theatre
- Pine Knob Music Theatre
- The Ark
- Renaissance Center
- Huntington Place
- Dequindre Cut
- Great Lakes Crossing Outlets
- University of Michigan Nichols Arboretum