Holiday houses in Windsor
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness and more.
Stylish South Walkerville Home w Hot-Tub & Firepit
Welcome to this Stylish Home Away From Home! 1 King Bed & Ensuite on the 2nd Floor. 2 Bedrooms (2 Queens+1 Top Twin Bunk) & Full Bath on the Main Floor + 1 Queen Bed in the Basement. Bring Together 1 or 2 Families of up to 9 people for your next visit to Windsor ON. Located in the Very Desirable Neighbourhood of South Walkerville. Enjoy an evening Soak in the Hot-Tub & a Relaxing Experience by the Gas Fire-Pit in the Backyard. Please note the basement has a kitchenette not currently functional.
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!
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
Blue Breeze Cottage Ontario
Tranquil Farmhouse Retreat with a Pet-Friendly Twist Welcome to your picturesque escape in the heart of Amherstburg, Ontario! Nestled on a peaceful street and mins away from Downtwon river front area. Whether you're a nature enthusiast looking to discover the beauty of Canada's southernmost tip, Point Pelee National Park, a wine connoisseur, or simply seeking a tranquil getaway to indulge in golf and visit museums, our Amherstburg retreat offers the perfect blend of relaxation and adventure
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.
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.
Victoria Ave - 1 BR apartment w fireplace
Available for monthly rental. Not 420 friendly. No smoking of any kind in apartment or on property. Private, light filled, warm apt in a character home on prestigious Victoria Ave. Furnished in Mid-century modern and Hollywood Regency decor. Includes a queen bed, gas fire place, modern kitchen with wifi and shared laundry room. Easy free street parking. Quick drive to Detroit Tunnel. Perfect for one or two people. A short walk to Hospital - Ouelette Campus - ideal for a daytime rest.
Beautiful 3Bedroom 2Bath Home free parking&laundry
Welcome to our spacious Midtown home away from home featuring 2 floors of living(main & upper stairs) that have been beautifully updated offering 3 bdrms 2 full baths, 2 living rms w/65”&55” TVs w/Netflix. Full kitchen w/stainless appliances, granite counters, covered front porch for enjoyment, fenced backyard. On a quiet block, close to transit, shopping, restaurants, ECRow, 401&Windsor-Detroit Tunnel. Private drive Ideal for families, out of town workers or large groups. Come & Relax!
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.
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!
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.
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
Other great holiday rentals in Windsor
Lakeshore Park lakeside getaway.
Cozy 1-Bedroom Retreat with Relaxing Sunroom
Luxury South Windsor Home- Gym & Sauna / Arcades
Serene Green 2BR Haven in Little Italy
Executive Condo. 3BR, King Bed w/ Ensuite
Bamoun- New Spacious 2BR+2Bath
Modern & Cozy Home Retreat
Full House - 5 Bed, 2 Bath - East
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $142 NZD | $143 NZD | $150 NZD | $150 NZD | $162 NZD | $154 NZD | $150 NZD | $160 NZD | $148 NZD | $148 NZD | $142 NZD | $143 NZD |
| 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 1,660 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, Ford Field, and Comerica Park
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Chicago Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Indianapolis Holiday rentals
- Pittsburgh Holiday rentals
- Downtown Chicago Holiday rentals
- Detroit Holiday rentals
- Townhouse rentals Windsor
- Rentals with a patio Windsor
- Rentals with lake access Windsor
- Fitness-friendly rentals Windsor
- Private suite rentals Windsor
- Rentals with outdoor seating Windsor
- Rentals with a washing machine and dryer Windsor
- Rentals with a fire pit Windsor
- Rentals with a fireplace Windsor
- House rentals Windsor
- Condo rentals Windsor
- Waterfront rentals Windsor
- Rentals with beach access Windsor
- Loft rentals Windsor
- Rentals with a hot tub Windsor
- Hotel rooms Windsor
- Smoking-friendly rentals Windsor
- Pet-friendly rentals Windsor
- Apartment rentals Windsor
- Rentals with an EV charger Windsor
- Rentals with pools Windsor
- Family-friendly rentals Windsor
- Rentals with breakfast Windsor
- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Michigan Stadium
- Comerica Park
- Detroit Zoo
- University of Michigan Museum of Art
- Mt. Brighton Ski Resort
- Motown Museum
- Alpine Valley Ski Resort
- Maumee Bay State Park
- Oakland Hills Country Club
- University of Windsor
- Forest Lake Country Club
- University of Michigan Historical Marker
- Kensington Metropark
- Huntington Place
- Fox Theatre
- Hollywood Casino at Greektown
- Great Lakes Crossing Outlets
- The Heidelberg Project
- Pine Knob Music Theatre
- Masonic Temple
- Renaissance Center