
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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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 Luxury 1BR Retreat in Prime Location
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!

Old Hollywood-EM Boutique Suites
Welcome to our Hollywood studio, where the glitz and glamour of Old Hollywood come alive! Perfectly situated in the heart of little Italy, this stylish retreat offers a unique blend of vintage elegance and modern comfort. Step back in time to an era of classic films and iconic stars, all inspired by the golden age of Hollywood. Unit includes: A luxurious king-size bed, large living room & dining space, full kitchen with S/S appliances & island, large bathroom with laundry and private balcony.

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.

Affordable Urban Bachelor
Our goal is to provide high quality accomodation at an affordable price. Welcome to our cozy bachelor unit where up to four guests can sleep comfortably. This stylish and budget-friendly retreat is perfect for solo travelers, couples, or small groups looking for accomodation in Windsor. Nestled in a prime location, you'll have easy access to everything that Windsor has to offer. Whether you're here for business or leisure, our bachelor provides a convenient and affordable home base.

Modern guest suite downtown
Self contained 1 bedroom suite nestled in the heart of downtown Windsor. This thoughtfully designed space combines both modern comfort and old world charm. Perfect for couples or solo travelers this unit features a separate entrance, stainless steel appliances, an oversized shower, spacious bedroom, large windows and laundry access. Relax and unwind in the fenced in backyard or enjoy the convenience of local shops, cafés, restaurants and vibrant nightlife just steps away.

"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

Come and relax at the BlueByU!
Beautifully decorated, blue-themed upper one-bedroom Executive Apartment. Ideal for business travel or romantic getaways. Conveniently located in the heart of Walkersville, the bright unit has a queen-sized bed, a beautiful kitchen and bathroom, a spacious dining area, a stunning living room, and a small office. We are located only 15 minutes from downtown Detroit via the tunnel, 15 minutes from Windsor’s airport, and 5 minutes from the Via train station.
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Private Room in Downtown Windsor w/Free Coffee

Windsor home - Room 2

Beautiful and Cozy Deluxe Ensuite

R14 B#10/6 Shared Basement Hostel Sud Windsor

Near restos, US border, 401, Nextstar, walmart

Private Room. Independent Entrance. #2

Professionals Favorite Place

Quiet and comfortable room #2
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £62 | £62 | £65 | £65 | £71 | £67 | £68 | £71 | £70 | £70 | £68 | £65 |
| 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 & 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
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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
- Motown Museum
- Indianwood Golf & Country Club
- Warren Community Center
- Seven Lakes State Park
- Rolling Hills Water Park
- Bloomfield Hills Country Club
- Oakland Hills Country Club
- Seymour Lake Township Park
- Maumee Bay State Park
- Seven Lakes Championship Golf & Estates
- Wesburn Golf & Country Club
- Mt. Brighton Ski Resort
- Grosse Ile Golf & Country Club
- Ambassador Golf Club
- Country Club of Detroit
- South Bass Island State Park