
Holiday houses 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.

Luxury South Windsor Home with Private Gym/Sauna
Come and stay at this 5-star inspired home! Over 3,200 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.

AKSUM- Location! Lovely Studio, Ensuite Shower, AC
We are in Windsor, Canada Enjoy a stylish experience at our centrally located unit of modern elegance and minimalism. Close to many of Windsor's key destinations Aksum is an independent unit with ensuite bathroom (shower) Walk to appointments at City Hall (2min), to the casino or Walkerville or scenic riverfront (5min), Downtown St. Clair and to restaurants You'll be at the Detroit tunnel in 1 min. Bus stop is just outside for easy access to train station and Univ of Windsor No visitors allowed.

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.

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!

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.

Walkerville Loft (Main floor unit)
Welcome to our charming loft nestled in the heart of a Walkerville in Windsor. This thoughtfully designed space combines modern comfort with historical 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 vibrant cafes just steps away. Immerse yourself in the city's rich history during the day and unwind in this stylish retreat at night.

Serene Green 2BR Haven in Little Italy
Welcome to this luxurious 2-bedroom home featuring European designer furniture — family-friendly and work-from-home ready. Enjoy 5-star hotel beds, a renovated kitchen with stainless steel appliances, free laundry, Wifi, standing desks, a plush velvet sofa with a 50" TV, and convenient on-street free parking. Centrally located in Windsor, just a 5–10 min walk to Italian dining and shops, with easy access to Windsor downtown, Detroit border, Highway 401, and Windsor Regional Hospital.

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!

"The Modern Loft" in Walkerville / 2Bed - 1 Bath
Enjoy a luxury modern experience in the heart of Old Walkerville. This modern 2 bedroom loft is newly renovated with luxury finishes while keeping century old details. Restaurants, pubs, cafes, retail all within a minute walk from this superb location. Stay here and get a taste of what Old Walkerville has to offer. DISTANCES TO: Casino - 2 minutes Downtown - 2 minutes Hospital - 5 minutes Detroit - 10 minutes Ford Field - 12 minutes Little Ceasers Arena - 12 minutes

Affordable 3 bedroom apartment
Welcome to your perfect getaway in the vibrant West End, just steps away from the university! Our spacious, fully functional three-bedroom apartment is ideal for larger groups and families looking for comfort and convenience. Enjoy a quiet space to relax, with three well-appointed bedrooms designed to ensure a restful night's sleep. Book your stay today and experience the perfect blend of location and comfort, tailored for memorable moments with your loved ones.
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Cozy & lovely room

Private Room in Downtown Windsor w/Free Coffee

Windsor home - Room 2

R14 B#10/6 Shared Basement Hostel Sud Windsor

Cozy room with dedicated bath!

Near restaurants, 401, Nextstar, walmart, parks

Private Room. Independent Entrance. #2

Professionals Favorite Place
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $143 NZD | $145 NZD | $152 NZD | $152 NZD | $164 NZD | $156 NZD | $159 NZD | $166 NZD | $163 NZD | $163 NZD | $157 NZD | $152 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 | 
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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
1,530 of Windsor holiday rentals include Wi-Fi 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
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- Ford Field
 - Little Caesars Arena
 - Point Pelee National Park
 - Comerica Park
 - Michigan Stadium
 - Detroit Zoo
 - Detroit Golf Club
 - University of Michigan Museum of Art
 - Indianwood Golf & Country Club
 - Motown Museum
 - Warren Community Center
 - Seven Lakes State Park
 - Rolling Hills Water Park
 - Seymour Lake Township Park
 - Bloomfield Hills Country Club
 - Oakland Hills Country Club
 - Wesburn Golf & Country Club
 - Seven Lakes Championship Golf & Estates
 - South Bass Island State Park
 - Maumee Bay State Park
 - Mt. Brighton Ski Resort
 - Ambassador Golf Club
 - Grosse Ile Golf & Country Club
 - Country Club of Detroit