Kid-friendly holiday rentals in Windsor

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Top-rated family-friendly rentals in Windsor

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Home in Windsor, Canada

4.88 out of 5 average rating, 117 reviews

Stylish South Walkerville Home w Hot-Tub & Firepit

Welcome to this Stylish Home Away From Home! 1 King Bed & Ensuite on the 2nd Floor. 2 Bedrooms (2 Queens+1 Top Twin Bunk) & Full Bath on the Main Floor + 1 Queen Bed in the Basement. Bring Together 1 or 2 Families of up to 9 people for your next visit to Windsor ON. Located in the Very Desirable Neighbourhood of South Walkerville. Enjoy an evening Soak in the Hot-Tub & a Relaxing Experience by the Gas Fire-Pit in the Backyard. Please note the basement has a kitchenette not currently functional.

9–16 Mar

$204 SGD per night

Guest favourite

Flat in Windsor, Canada

4.94 out of 5 average rating, 187 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.

20–27 Sep

$117 SGD per night

Guest favourite

Guest house in Kingsville, Canada

4.98 out of 5 average rating, 598 reviews

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.

31 Oct – 7 Nov

$155 SGD per night

Guest favourite

Home in Windsor, Canada

4.93 out of 5 average rating, 105 reviews

Waterfront Home in Central City -KING BED 4 guests

Unwind in the newly renovated stylish WATERFRONT Home on Riverside Drive St of Windsor. Central City is full of Casino, restaurants, bars, shops, historic landmarks, and attractions. Adventure through Windsor and the region easily from this prime location. Once you are ready to relax, retreat to our comfy Home. ✔ 1.5 Rooms with King - 1 Twin size Beds ✔ Scenic Living room ✔ 2 Full washrooms ✔ Open Concept Living Area ✔ Office Space ✔ High-Speed Wi-Fi ✔ Central AC/HEAT ✔ Parking for 4 cars

9–16 Mar

$246 SGD per night

Guest favourite

Guest house in Essex, Canada

4.99 out of 5 average rating, 296 reviews

Private Wine Route Getaway with Hot Tub

The heart behind The Vineyard Retreat is to help our guests relax, restore, and reconnect. Located on County Road 50 we're conveniently placed on the wine route between Kingsville, Colchester, and Harrow. Our guest house is steps away from Lake Erie and close by to wineries, breweries, restaurants, tours, fruit stands, national parks, conservation areas, beaches, orchards, golf courses, bike paths, and more. Read more about what our guest house has to offer in the detailed description below.

28 Dec – 4 Jan

$232 SGD per night

Guest favourite

Guest suite in Windsor, Canada

4.92 out of 5 average rating, 105 reviews

Covid Clean 2 bdrm Entire Lower Level Sport Themed

This private spacious 2 bedroom lower level sport themed/sport pool backyard getaway is nestled in the heart of South Windsor, ON Canada. This space is unique, clean and well maintained and is sure to exceed your expectations! This quiet and safe neighborhood is conveniently centered near everything -International bridge, major roads highways & expressway, shopping, restaurants & casino. Ideal for workers, couples, business traveller’s. Come enjoy the space but absolutely NO CRAZY PARTIES

30 Aug – 6 Sep

$85 SGD per night

Guest favourite

Home in Kingsville, Canada

4.96 out of 5 average rating, 157 reviews

Heritage Lakehouse

Unwind at this modern lake house situated right on Lake Erie. The house was built with high ceilings and exposed raw steel accents throughout. Enjoy a stunning view of lake Erie from both bedrooms or through the 14 ft glass wall in the living room. The kitchen boasts all new appliances, quartz countertops and all of the cooking supplies needed. The house is located in between two public beaches and offers its own access into the lake. Wineries, Pelee Island, restaurants and golf courses.

15–22 Oct

$215 SGD per night

Guest favourite

Cottage in Lakeshore, Canada

5.0 out of 5 average rating, 116 reviews

Beau Chalet de Pointe-aux-Roches (No Cleaning Fee)

Bienvenue / Welcome to the village of Pointe-aux-Roches / Stoney Point in Lakeshore, Ontario. Available May thru October, this cozy lakefront cottage-home is fully furnished for your comfort on the southeastern shore of Lake St. Clair, offering beautiful summer sunrises and sunsets. Shallow and warm Lake St. Clair, part of the Great Lakes system, is the connector lake between Lakes Huron and Erie, and has among the largest variety of fresh-water fish and aquatic species in the world.

1–8 Oct

$221 SGD per night

Guest favourite

Guest suite in Windsor, Canada

4.98 out of 5 average rating, 160 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.

20–27 Sep

$116 SGD per night

Guest favourite

Guest suite in Windsor, Canada

4.92 out of 5 average rating, 309 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 late March to early November at 32°C (90°F). The hot tub is open year round.

17–24 Dec

$159 SGD per night

Guest favourite

Guest house in Flat Rock, Michigan, US

4.98 out of 5 average rating, 138 reviews

Steve’s Barn Lodge, Detroit River/Erie fishing

Beautiful and fun family-friendly retreat! Close to Metro Airport! Pet friendly. Perfect for out of town Detroit River/Lake Erie fisherman. Very private rural location with private access to Metro Park. An “Up North feel”. Lots of safe parking for your boat(s). 10 miles from Lake Erie Metro Park boat launch to fish the river or Erie. Quick 16 mile drive to Sterling State Park. Close to restaurants. Full kitchen and bathroom.

22–29 Sep

$176 SGD per night

Guest favourite

Farm stay in Amherstburg, Canada

4.98 out of 5 average rating, 171 reviews

MK Getaway

Escape from reality to MK Getaway, a modern one bedroom farmhouse located in Amherstburg. Amherstburg is a historic town with a beautiful waterfront and the most beautiful sunsets. We are located at the beginning of epic wine country. Our cottage offers one bedroom, one bath, a kitchenette and wifi.

5–12 Jul

$174 SGD per night