
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.

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.

Ray's iNN Olde Riverside (all private)
PRIVATE GUEST SUITE with OWN ENTRANCE. Boutique Hotel Suite inspired,offering amenities,privacy & charm.50”Samsung TV+Netflix.This Suite has a KITCHENETTE with SINK also mini-fridge,microwave,toaster-oven,slow-cooker, cooktop,coffee maker,kettle.PRIVATE BATHROOM with stand up shower.Includes dishes, glassware,utensils, towels,linens,coffee.Seasonal PATIO & lovely landscaping. Within Olde Riverside,close to shops,restaurants,grocery,parks, WFCU Centre.Short walk to a beautiful riverfront & trail.

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!

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!

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

Luxury South Windsor Home with Private Gym/Sauna

Serene Green 2BR Haven in Little Italy

Rare find by the Riverside

Modern Riverside Escape | Stylish & Cozy Stay

AKSUM- Location! Lovely Studio, Ensuite Shower, AC

Private/Quiet Perfect for professionals!

Affordable Urban Bachelor

Private Guesthouse in South Windsor
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 71 | € 72 | € 75 | € 75 | € 81 | € 77 | € 75 | € 80 | € 74 | € 81 | € 78 | € 75 |
| 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
How is the weather in Windsor?
Windsor has a humid continental climate with four distinct seasons. Summers can be hot, reaching up to 86°F (30°C), while winters are cold with temperatures dropping to around 20°F (-6°C). Snowfall is common in winter, which makes for great winter sports activities.
What are some of the best things to do in Windsor?
In Windsor, you can explore the unique outdoor art at Windsor Sculpture Park, tour the historic Willistead Manor, or enjoy a day of fun at the Adventure Bay Family Water Park. Nature lovers also enjoy hiking the trails in Devonwood Conservation Area.
What is the best time of year to visit Windsor?
The most popular time to visit Windsor is during the summer months from June to August. This is when you can enjoy the Windsor Summer Fest, an annual festival with carnival rides, concerts, and fireworks. The warm weather also allows for exploration of the city's outdoor attractions.
What are the best places to stay in Windsor?
Downtown Windsor is a popular area to stay due to its easy access to restaurants, shops, and attractions like the Art Gallery of Windsor. Walkerville, known for its historic charm, and Riverside, with its waterfront views, are also frequently suggested.
What are the best places to visit in Windsor?
Visitors often enjoy exploring the Windsor Sculpture Park, filled with quirky outdoor art, or touring the historic Willistead Manor. The Adventure Bay Family Water Park is also a frequent favorite, especially for those traveling with children.
What are some hiking trails in Windsor?
Windsor is home to several hiking trails. The Ganatchio Trail, running along the Detroit River, is perfect for waterfront views, while the Little River Extension offers winding paths through lush greenery. For a forested hike, try the Devonwood Conservation Area.
What are some family activities to do in Windsor?
Take the family for a fun-filled day at the Adventure Bay Family Water Park, or explore the exhibits at the Windsor Science Centre. For a more relaxed day, pack a picnic and head to the Peche Island, a 100-acre island with trails, wildlife, and picnic spots.
What are some of the best day trip ideas in Windsor?
You could take a day trip to Point Pelee National Park, an excellent destination for bird watching and hiking, located just 60 minutes (60 miles/97 km) away. Alternatively, visit the Detroit Science Centre, a quick 10 minutes (3 miles/5 km) trip across the Detroit River.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 380 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 910 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Windsor have a gym?
Absolutely! We offer over 60 house rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Windsor?
Windsor has more than 360 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windsor have wifi?
Absolutely! We offer over 720 house rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there Windsor house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Windsor, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Windsor?
Experience the best of Windsor with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Windsor have air conditioning?
Absolutely! We offer over 690 house rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Windsor?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with a bbq area, over 60 homes with a gym, over 720 homes with wifi, over 690 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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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- Ford Field
- Michigan Stadium
- Little Caesars Arena
- Point Pelee National Park
- Comerica Park
- Detroit Zoo
- University of Michigan Museum of Art
- Detroit Golf Club
- Motown Museum
- Indianwood Golf & Country Club
- Warren Community Center
- Seven Lakes State Park
- Grosse Ile Golf & Country Club
- Mt. Brighton Ski Resort
- Rolling Hills Water Park
- Ambassador Golf Club
- Bloomfield Hills Country Club
- Seymour Lake Township Park
- Wesburn Golf & Country Club
- Seven Lakes Championship Golf & Estates
- Oakland Hills Country Club
- Maumee Bay State Park
- South Bass Island State Park
- Country Club of Detroit




