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.

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Top Guest favourite

Apartment in The Core

4.95 out of 5 average rating, 266 reviews

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.

Top Guest favourite

Home in South Windsor

5 out of 5 average rating, 30 reviews

South Windsor Luxury Home - 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.

Guest favourite

Apartment in Windsor

4.89 out of 5 average rating, 151 reviews

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!

Top Guest favourite

Apartment in The Core

4.97 out of 5 average rating, 33 reviews

Farmer's Market, Balcony, 24/7 Gym, IPTV

Welcome to the beautiful & luxurious Boutique apartment building - The Bitcoin Building - located in the heart of the city. Enjoy a rejuvenating sleep on our BeautyRest hotel style mattresses, TV w/ Amazon fire stick w/ 1000s of channels/Movies. Elegant furniture, a cool LED fireplace & fully stocked kitchen will leave you wanting to stay longer. Includes access to 24/7 Fitness Gym. Perfectly situated on Downtown Windsor's nicest street you are a short walk away from everything the core offers.

Top Guest favourite

Home in Riverside

4.97 out of 5 average rating, 106 reviews

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

Superhost

Home in Riverside

4.81 out of 5 average rating, 181 reviews

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

Guest favourite

Home in The Core

4.94 out of 5 average rating, 159 reviews

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.

Top Guest favourite

Guest suite in Riverside

4.98 out of 5 average rating, 214 reviews

Glenn & Deb’s Place

1100 sq. ft guest suite attached to main residence but completely separate space on quiet residential street. Upper level with two bedrooms, washer/dryer and 1 bathroom with custom shower. Lower level has full kitchen, living room with gas fireplace, 42'' television and high speed internet. Independent heating and cooling. Owners are on site for quick response to all your needs. Close to WFCU, Caesars Windsor and all major arteries. We regret we are unable to accommodate pets.

Guest favourite

Villa in Windsor

4.9 out of 5 average rating, 185 reviews

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Located by the river, a 5 minute drive from the shopping center. This 4-bedroom home is equipped with fully furnished living and dining areas, as well as a backyard spot perfect for fishing, boating, canoeing, and winter ice skating. The yard, among the river, features a fire pit, a tree swing, and multiple sitting areas. You will enjoy traveling downstream by boat into the Detroit River bay, or taking a short drive to nearby attractions, shopping areas, and local restaurants.

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 376 reviews

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.

Top Guest favourite

Farm stay in Essex

4.99 out of 5 average rating, 175 reviews

Luxury Farm Stay - Hot tub - Allow pets - Firepits

-Breathe in the presence of nature- You will quickly fall in love with the quiet pace, beautiful nature, and fabulous food and wine on County Road 50. This luxurious cottage hideaway is surrounded by wildlife and farmland. Private access to idyllic grounds that span over 225 acres of farmland, creeks, and with frontage onto majestic Lake Erie. Bathe in our farm and forests' healing power. Town of Essex License #STR-2022-28

Guest favourite

Home in The Core

4.94 out of 5 average rating, 148 reviews

"The Oasis" a Walkerville dream / 2 Bed - 1 Bath

Kick back and relax in this calm, stylish space. This uniquely renovated century home is located in the heart of Old Walkerville and is just a few steps from all the beauty this area 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

Holiday rentals for every style

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Popular amenities for Windsor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Windsor's top sights

Little Caesars Arena140 locals recommend

Ford Field124 locals recommend

Detroit Institute of Arts203 locals recommend

Eastern Market72 locals recommend

Campus Martius Park District133 locals recommend

Motown Museum140 locals recommend

Other great holiday rentals in Windsor

Superhost

Apartment in The Core

4.77 out of 5 average rating, 95 reviews

luxury 2-Bedroom Apartment In Downtown Windsor

NkemRating, 5 stars3 weeks ago

Unfortunately we couldn't find the dishwasher, but everything else was great.

Guest favourite

Guest suite in Windsor

4.84 out of 5 average rating, 31 reviews

Spacious 1BD Apartment | Prime Location

NicoleRating, 5 stars1 week ago

very friendly and accommodating host, her professionalism really stupid very quick to respond had a peaceful stay here would definitely book again 10/10

Top Guest favourite

Home in The Core

4.96 out of 5 average rating, 47 reviews

Boutique Suite on the River

SuzanneRating, 5 stars2 weeks ago

We really enjoyed our stay in this home, which has a great location near the waterfront. The house itself is cozy and beautifully decorated, perfectly blending charm with modern amenities. I particularly appreciated the comfortable bed, which ensured restful nights after long walks exploring the waterfront and the town of Walkerville. The host is very attentive and friendly, making us feel welcome. Thank you, Michele! If we come back to Windsor, we would look forward to staying here again! Suzanne & Dave

Top Guest favourite

Home in Windsor

5 out of 5 average rating, 92 reviews

Luxurious 3BR, King Bed, Ensuite. Perfect Stay!

ToshaRating, 5 stars3 days ago

In the beginning we had a small issue, Olivia was responsive and quickly resolved it. I was apprehensive about renting a town home, however I was pleasantly surprised. The home is elegant, spacious and well maintained. The neighborhood is really peaceful, and is in a great location. Olivia and her staff were professional and very friendly. We highly recommend and would stay there again for our future visits.

Guest favourite

Apartment in Windsor

4.88 out of 5 average rating, 16 reviews

Luxury Unit Windsor (4-plex)

MohamedRating, 5 stars2 months ago

Great host, great home! The process was very smooth and we felt right at home.

Superhost

Bungalow in Windsor

4.76 out of 5 average rating, 42 reviews

One bed room house with one Qween bed

AndrewRating, 5 stars3 weeks ago

The skylight in the kitchen is very cozy, the bed is comfortable, and the bathroom is clean and spacious. The living room is a bit bland though, so I stayed in the kitchen until bed time.

Guest favourite

Apartment in Windsor

4.89 out of 5 average rating, 44 reviews

Rare find by the Riverside

SheritaRating, 5 stars4 days ago

Very affordable very clean , balcony you can see ambassador bridge loved the home decor everything looked exactly as pictured would recommend and stay again !!!

Guest favourite