Vacation rentals in Windsor
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
Lakeview Inn
The Lakeview Inn sits on the North Shore of beautiful Lake Erie. This modern lakehouse is an 8 minute drive to the centre of kingsville where there is multiple breweries and restaurants, a public beach is a 1 minute drive down the road and is right in the centre of Southern Ontario's Wine Country. If you're coming down for a weekend to relax, taste wine or to enjoy the exceptional birding the area has to offer. At the end of your day relax to the sound of the waves brushing up against the shore.
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!
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!
Small lake house on Lake Erie shore
Private Bachelor apartment sized house directly on Lake Erie. ULTRA FAST WI-FI, Private deck, Kayaks. The Cottage is always toasty warm all winter long. Queen bed, bathroom with shower, kitchenette. Great swimming in shallow, sandy waters. Cottage is only a few minutes from many area wineries, breweries, distilleries and fantastic restaurants serving local food. Walking distance to Pelee Island ferry. Want something completely different? This is the place. It's almost like staying on a boat.
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.
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.
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!
Cozy Forest Retreat • Sauna • Hiking • Event Space
Escape to Kings Woods Lodge for a cozy winter getaway! Enjoy hiking in the woods, bird watching, crackling fires, heated blankets, rejuvenating sauna sessions, and nights filled with board games and shuffleboard. Surrounded by peaceful forest views, it’s the perfect spot to relax and reconnect. Hosting an event? Kings Woods Hall, our boutique on-site venue, is just steps away and can host up to 80 guests. Great for Christmas parties, bridal or baby showers or intimate weddings.
Couple's Romantic Retreat with hot tub, fire pit.
Romantic and soothing discreet hideaway. Come to relax, reunite and enjoy the night. This beautiful unit features: -private backyard Oasis with Hot tub, cedar Gazebo, outdoor Tv and sound bar, 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.
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor
JP's Dream House
Luxury South Windsor Home with Private Gym/Sauna
little Belle River home
Serene Green 2BR Haven in Little Italy
Rare find by the Riverside
Watkins Bridge House
Private Clean Suite Getaway |Work & Relax in Style
The Ambassador’s Stay • Bright 3BR Family Retreat
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $82 | $83 | $87 | $87 | $94 | $89 | $87 | $93 | $86 | $94 | $90 | $87 |
| Avg. temp | 26°F | 28°F | 37°F | 49°F | 60°F | 70°F | 74°F | 72°F | 65°F | 53°F | 41°F | 31°F |
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 vacation rentals in Windsor
Total vacation rentals
Explore 1,570 vacation rentals in Windsor
Verified guest reviews
Over 85,620 verified reviews to help you choose
Family-friendly vacation rentals
640 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 380 rentals that welcome pets
Vacation rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
910 properties have a dedicated workspace
Wi-Fi availability
1,530 of Windsor vacation 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
- Greater Toronto and Hamilton Area Vacation rentals
- Chicago Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Downtown Chicago Vacation rentals
- Indianapolis Vacation rentals
- Pittsburgh Vacation rentals
- Detroit Vacation rentals
- Condo rentals Windsor
- Cottage rentals Windsor
- Rentals with a fireplace Windsor
- Rentals with a washer and dryer Windsor
- Waterfront rentals Windsor
- Rentals with breakfast Windsor
- Fitness-friendly rentals Windsor
- Rentals with a fire pit Windsor
- Loft rentals Windsor
- Rentals with beach access Windsor
- Rentals with lake access Windsor
- Rentals with a patio Windsor
- House rentals Windsor
- Rentals with outdoor seating Windsor
- Family-friendly rentals Windsor
- Apartment rentals Windsor
- Smoking-friendly rentals Windsor
- Townhouse rentals Windsor
- Hotel rooms Windsor
- Rentals with pools Windsor
- Rentals with an EV charger Windsor
- Private suite rentals Windsor
- Pet-friendly rentals Windsor
- Rentals with a hot tub Windsor
- Ford Field
- Little Caesars Arena
- Comerica Park
- Point Pelee National Park
- Michigan Stadium
- Detroit Zoo
- University of Michigan Museum of Art
- Detroit Golf Club
- Motown Museum
- Warren Community Center
- Indianwood Golf & Country Club
- Mt. Brighton Ski Resort
- Grosse Ile Golf & Country Club
- Seven Lakes State Park
- Seymour Lake Township Park
- Ambassador Golf Club
- Wesburn Golf & Country Club
- Rolling Hills Water Park
- Oakland Hills Country Club
- Bloomfield Hills Country Club
- Eastern Market
- Seven Lakes Championship Golf & Estates
- Maumee Bay State Park
- South Bass Island State Park
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes