Family-friendly holiday rentals in Chestermere

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chestermere

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

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Guest favourite
Home in Chestermere
5 out of 5 average rating, 10 reviews

Modern 4-Bedroom Retreat – Near the Lake, Sleeps 8

Enjoy a family friendly property with a fully fenced yard in Chestermere. Features include a living room with 58" smart tv, 2 dining areas, laundry room, full kitchen with dishwasher and large pantry, plus 4 bedrooms (2 with ensuites and walk in closets) on the upper floor. The kitchen has a stove, oven, fridge with icemaker, microwave, stocked coffee bar, and large island. Steps from Chestermere Lake, trails, restaurants, & shops. Perfect for families, large groups, & outdoor lovers year-round.

Superhost
Home in Belvedere
5 out of 5 average rating, 3 reviews

Brand New 3BR Modern Duplex | 15 Min DT Calgary

Brand New Modern 3BR Duplex in Belvedere w/ King Master Suite Step into this stylish, freshly built duplex with spacious open living, dining, and kitchen—ideal for families, groups, or professionals. Just 15 min to downtown Calgary, 10-15 min to YYC airport, near East Hills shopping, 90 min to Banff. Sleeps up to 8: King master with ensuite & walk-in closet, two queen bedrooms, plus living room pull-out couch. Fast Wi-Fi, large TV, and dedicated parking pad. Your fresh, comfortable homebase

Top guest favourite
A modern living space is showcased with a stylish white sectional sofa and a glass coffee table featuring decorative elements. A sleek fireplace is framed by a stone wall, while built-in shelves provide storage and display areas. Soft lighting enhances the welcoming atmosphere.
Home in Tuxedo Park
4.82 out of 5 average rating, 193 reviews

Spacious, clean, downtown, cozy home 3Bed + 3Bath

Looking for a beautiful, peaceful and modern place, just outside the heart of downtown Calgary? Enjoy a spacious place kept in mint condition, very clean, quiet neighborhood 2,500 square feet Newly renovated BBQ All amenities Street parking Air conditioning + Heating Car to go zone Bus + transit Full kitchen + utensils 3 min walk to convenience store, 16th Ave and Center street, restaurants, gyms, parks, leisure center etc Family owned. Reserve your dates today, we book up FAST.

Top guest favourite
A spacious lawn extends towards a calm lake, with several docks visible across the water. Two red chairs are positioned near a fire pit, and a zip line is seen in the background. The surroundings are lush and well-maintained, inviting relaxation by the water.
Home in Chestermere
4.9 out of 5 average rating, 86 reviews

Lake front two bedroom walk out basement house

Bring your family to this lakefront walk out lower level of the house with two queen bed . There is wood burning fireplace,a big yard with zip line and play ground perfect for a family with kids getaway . There’s a fire pit out side, the dock to sit and enjoy the lake. The yard is shared with owners (respectful family of 4 and friendly dog) living upstairs. Please park in the driveway. It’s only 20 minutes to downtown Calgary . Your host is Adi and Neil Let us know if you have any questions.

Top guest favourite
The modern kitchen features light grey cabinetry and a central island with red stools. Stainless steel appliances include a refrigerator, oven, and microwave. A window allows natural light, and a vase with flowers adds a touch of color to the countertop.
Home in Tuscany
4.87 out of 5 average rating, 197 reviews

Cozy spacious 4BR home | AC& BBQ | close to Banff

Nice, cozy, and stylish home that is perfect for any stay. Located in the young quiet community of Tuscany, it is surrounded by many amenities. The grocery store and gas station are all within a 10-minute walk and a couple-minute drive. There is a train station located 15 minutes away by foot, connecting you to the whole city. The home has a new fully equipped kitchen, a smart TV in the living room, and a free in-home washer and dryer. Our 4 bedrooms are great and spacious for up to 8 guests.

Guest favourite
A bright living room is characterized by light walls and a spacious layout, featuring a large smart TV on a contemporary media unit. Comfortable white sofas are arranged around a dark coffee table, with decorative plants and art pieces adding subtle charm.
Home in Calgary
4.84 out of 5 average rating, 111 reviews

Newly Near Banff CrossIron Mills entry lux family

This stylish place to stay is perfect for group trips. Less than 15 minutes from the airport. It's in a quiet family neighborhood & is conveniently close to tons of shopping (Costco, Crossiron Mills, T&T supermarket nearby). You'll love the 4 comfortable bedrooms with 1 king bed and 3 queen beds , 2 livingrooms, 3 full bathrooms, bright kitchen and big backyard. Smart TV with Netflix. Fast speed internet. Great view to Rocky Mountain from the upper floor. 1 hour to Banff through Stoney Trail.

Guest favourite
A modern kitchen is highlighted by white cabinetry and a large island with bar seating. Stainless steel appliances include a refrigerator and stove, while natural light floods the space through wide windows. Decorative wall art adds a subtle touch to the contemporary design.
Home in Mahogany
4.89 out of 5 average rating, 142 reviews

~PrivateFencedYard | 2FamilyRms | SunshineYellow

*Private fenced yard* *4 Bedrooms and 2 and half bedrooms* *2 separate family rooms* *Family-friendly space* *Super close to kids Play park* *Calgary's most exclusive and high-end neighbourhood: Mahogany!* Enjoy endless natural spaces, including multiple parks & walking and biking paths, & the Mahogany Wetlands. Close to the South Health Campus! Mahogany has quick access to nearly any place in Calgary owing to its close proximity to both 22x & Deerfoot! Zip anywhere you need super quickly!

Guest favourite
A modern living area is highlighted by a stylish stone fireplace, adorned with a large screen showcasing mountain scenery. Surrounding shelves contain various plants and decor items. A comfortable gray sofa is positioned nearby, with a decorative blue pillow, and a small plant is placed on the dark coffee table.
Home in Glenbrook
4.88 out of 5 average rating, 144 reviews

HotTub, 3 King Beds & Double Car Garage

Experience the pinnacle of comfort in our brand-new 5-bedroom duplex infill in SW Calgary. With 3 opulent king beds, a relaxing hot tub, and a double detached garage, this home redefines luxury. The full basement suite with full-size appliances, indoor fireplace, and top-tier finishings offer an unforgettable stay. Live the high life in Calgary! This spacious retreat is perfect for families or groups seeking comfort and style. Unwind in the private hot tub after a day of exploring the city.

Top guest favourite
The exterior of the residence features a two-story design with a stone façade and a spacious garage. Large windows illuminate the front, while a driveway leads from the street. Greenery is present alongside the home, contributing to the overall inviting appearance.
Guest suite in Aspenwoods
4.97 out of 5 average rating, 395 reviews

NO CLEAN FEE*Modern Basement with own entrance

Relax with the whole family at this peaceful place to stay. Our place has a door separating upstairs and basement and a private entrance and in an affluent area of Calgary. It's quiet, safe and boasts panoramic views of Aspen Woods. Only a 5 minute walk to Aspen Landing and Blush Lane Organic Market where you will find a variety of restaurants, pharmacies, coffee shops, grocery, liquor stores & more. 5min drive to C-train and 15 min drive to downtown. A quick drive to Banff and airport.

Top guest favourite
Home in Edgemont
4.93 out of 5 average rating, 307 reviews

Ravine Retreat, 4000+sqf, Luxury, AC,PoolTable etc

Welcome to beautiful and spacious Ravine Retreat House: - 4000+sqf , walk out to breathtaking ravine, Mountain View - Pool table entertainment - Free parking, Free bath and kitchen essentials, Free WiFi - Fully stocked kitchen; BBQ at balcony - Costco, superstores nearby - City centre, YYC airport 15 mins - Quick access to Banff - 6 bdrm 3.5 bath, - 10 beds: 7 twin +2 queen+1 king - A/C - Pet friendly (fee applied) - Perfect for multi-families, maximum 5 cars or 15 people at any time

Top guest favourite
An outdoor swim spa is situated on a patio, overlooking a well-maintained backyard and Chestermere Lake. Lush greenery surrounds the area, and gentle ripples on the water reflect the warm colors of a sunset in the background.
Home in Chestermere
4.98 out of 5 average rating, 85 reviews

Beautiful Lakefront 5-Bed home w/ outdoor swim spa

Located just 10 minutes outside of Calgary, this beautiful lakefront home is equipped with a full-size outdoor swim spa overlooking Chestermere lake, a massive backyard, pool table, outdoor fire pit, and more. The spacious home is perfect for families and larger groups to enjoy. Parking: Large driveway fits up to 4 vehicles with space for 2 additional cars on the street in front of the house. **Guests must review and acknowledge all house rules prior to booking being confirmed.

Top guest favourite
The spacious living room features large windows that provide natural light and views of the surrounding trees. A mix of comfortable seating options is arranged around a glass coffee table. Vintage decor, including a classic television stand, adds character to the room.
Townhouse in Collingwood
4.94 out of 5 average rating, 251 reviews

Soak Up the Retro-Inspired Vibe at This Inner City Gem

Curl up on the couch and unwind with some board games at this charming retreat on a tree-lined street. This gateway to the mountains combines bright, neutral decor with vintage details and wooden ceilings for a cabin-like feel. A desirable area boasting many paved bike and walking paths running along Confederation Golf Course and only 1 block from Confederation Park. Public transit, Jubilee Auditorium, SAIT, University of Calgary and McMahon Stadium are all nearby.

Popular amenities for Chestermere family-friendly rentals

When is the best time to visit Chestermere?

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Avg. price$132 SGD$132 SGD$117 SGD$122 SGD$138 SGD$186 SGD$208 SGD$173 SGD$145 SGD$141 SGD$136 SGD$153 SGD
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Quick stats about holiday rentals that are family-friendly in Chestermere

  • Total holiday rentals

    Explore 80 holiday rentals in Chestermere

  • Nightly prices starting at

    Chestermere holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,000 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Chestermere holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chestermere rentals

  • 4.8 Average rating

    Chestermere stays are highly rated by guests – averaging 4.8 out of 5!