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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Top guest favourite
A bright, open space is seen featuring modern wooden cabinetry and a cozy dining area with a multi-stool table. Dark brick accents contrast against light walls, while a glimpse of a comfortable bedroom is visible through the doorway. Natural light filters in through large windows.
Guest suite in Ramsay
4.97 out of 5 average rating, 191 reviews

Craftsman's Loft: Heritage charm with AC, 5 min DT

Welcome to the Craftsman's Loft! Relax and unwind in our sunny and cozy historic loft built in 1911! It has been lovingly modernized while maintaining its old-world charm. Be a part of the vibrant community of Ramsay and Inglewood, Calgary's oldest neighborhoods. Steps away from some of Calgary's finest restaurants, a thriving art and cultural scene, breweries and city life. Enjoy the convenience of a central location yet the comforts of a residential street lined with beautiful character homes.

Top guest favourite
A modern living area features a white sofa adorned with decorative pillows, positioned near large floor-to-ceiling windows that showcase city views. A round wall clock and a small plant add subtle decorative touches, while soft lighting creates a calm ambiance.
Apartment in Beltline
4.88 out of 5 average rating, 155 reviews

Best Location and Best View in all of Calgary

This 1 bed condo with stunning views is located in the heart of the city. You can walk to everything you desire within 15min or even shorter city scooter ride. The Ctrain is also a 5 min walk that opens up the rest of Greater Calgary and the 300 bus that goes straight to and from the Calgary airport YYC. Walking distance to restaurants, bars, casinos, grocery stores and parks. 2 hour drive to Lake Louise, 1.5 hour to Banff. Movies, shows, and over 5000 Nintendo and snes games to keep you happy.

Guest favourite
A modern living room features floor-to-ceiling windows showcasing the city skyline and distant mountains. A comfortable sofa faces a coffee table, with a flat-screen TV positioned nearby. A dedicated work station with a chair is set against the wall, accented by gentle greenery.
Flat in Beltline
4.93 out of 5 average rating, 136 reviews

DT Views |King Bed |Mins to Saddledome |UG Parking

Welcome to our stunning downtown Calgary corner unit condo! This modern retreat offers you the perfect combination of convenience, luxury, and breathtaking views. As you step inside, you'll immediately be captivated by the floor-to-ceiling windows that showcase the stunning city skyline and majestic mountain vistas. Please be aware that the front doors of the building lock at 10 pm. If you book, you'll have to pick up the key/fob in a different location. *** POOL is closed for the winter.

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, 138 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!

Top guest favourite
A cozy bedroom features a queen-sized bed with a soft blanket and a decorative throw. Nightstands with lamps are positioned on either side, and floral wall art adds a colorful touch. Natural light enters through curtained windows, creating a calm atmosphere.
Guest suite in Deer Ridge
4.99 out of 5 average rating, 138 reviews

☆ Private 1BR Suite ♥ Full Kitchen Laundry FP Wifi

Enjoy private separate entry to this clean and well-appointed lower level one bedroom suite. Equipped kitchen, in-suite laundry, private parking and outdoor space. Ideal for longer stays, perfect for one or a couple. → Fully equipped kitchen with dishwasher, stove, microwave, etc. → Cozy bedroom with Serta queen mattress → Gas fireplace, open concept living, TV → Work space + wi-fi → Spacious 4pc bathroom → Laundry → Off-street parking Legal secondary suite has dedicated heat/ventilation.

Guest favourite
Guest suite in Elboya
4.84 out of 5 average rating, 491 reviews

Cozy WindsorPark 1BR suite with separate entry

This is a long-term rental unit with minimum 6 months of stay. We will refund your Airbnb service fee after you checkout. If you need additional months, please send us an inquiry. Our one-bed room suite has separate entrance and a private bathroom. The suite is about 550 sq. feet and located in the inner city of Calgary. Super convenient location for almost everything you need, only 300 meters to grocery stores, restaurants, coffee shops and bus stops, nearby Chinook Mall, Calgary Stampede.

Top guest favourite
A light-filled living area is presented, featuring a spacious sectional sofa adorned with various cushions. A low coffee table is positioned centrally on an area rug, and a wall-mounted television is visible across from the seating. Large windows provide natural light and views of the outdoors.
Guest house in Southwest Calgary
4.98 out of 5 average rating, 213 reviews

Luxury private carriage house with character!

Enjoy a stylish experience in this bright and open carriage house located in a very desirable part of the city. Close to restaurants, shopping, downtown, the Saddledome, Mount Royal University, and much more! The architect-designed suite is one of a kind and full of character and natural light. Relax with a coffee or a glass of wine on the covered private balcony or take a short walk to Marda Loop, one of Calgary's premier dining destinations! Max occupancy is 2 adults & 1 child under 12.

Superhost
A spacious living area is highlighted by a modern sectional couch adorned with colorful throw pillows and a soft throw blanket. A wooden coffee table sits in front, with a lamp beside it. Large windows allow natural light to fill the room, surrounded by plants and a textile wall hanging.
Home in Bridgeland - Riverside
4.89 out of 5 average rating, 157 reviews

Funky 1 BR Century Home-Near DT, C-train

Funky, spacious boutique 1 bedroom home in a top/down duplex nestled in the heart of Bridgeland. Steps away from the trendy 1 avenue street with restaurants and all the amenities you need, and yet in a picturesque and quiet street! A quick drive to the DT core, walking distance to C-train. This elegant home features a 1 bedroom with comfy queen bed, bright, comfortable living spaces, fully equipped kitchen and clean bathroom!! Access to ✔free Wi-Fi ✔coffee ✔free parking ✔netflix ✔Laundry

Guest favourite
A welcoming living room features comfortable seating on a plush rug, with a large television mounted on the wall. A small table displays decorative items, and soft lighting is provided by a floor lamp. A painting of a flower adds a touch of elegance to the space.
Guest suite in Saddle Ridge
4.93 out of 5 average rating, 109 reviews

Charming Guest suite in Northeast Calgary

Our charming legal basement suite, 15 min drive to Calgary international airport offers comfort and tranquility that offers a home away from home experience - tasteful furnishings with WI-FI, washer and dryer, king and queen size beds, baby crib (Available on request) and a well-equipped kitchen. it's also; -6 min to Ctrain station -18 min to Cross Iron Outlet Mall. • 1 hr 30mins to Canmore(Banff)/Drumheller Come and relax in this cozy and peaceful community, book your stay today!

Guest favourite
A bright sleeping area features a spacious bed dressed in soft bedding against an accent wall in a warm hue. A cozy chair provides additional seating. The kitchenette showcases a modern design with essential appliances and a designated coffee area. The bathroom contains a shower stall and essential toiletries.
Guest suite in Banff Trail
4.76 out of 5 average rating, 113 reviews

Entire 1BDR Suite Direct Entrance | Papaya Suite

Welcome to Papaya Suite! Brand new thoughtfully designed 200 SQF suite for only ONE traveller -Ground entrance and entire space all to yourself -Queen size bed with comfortable mattress and bedding -Large solid wood table for working area -Bath with shower stand and toilet -Mini Kitchenette with sink, microwave, fridge, coffee maker, toaster and etc. -2 min walk to Banff Trail LRT station -Free street parking and WIFI -Check in before 9pm and quite time is 10pm to 9am next day

Top guest favourite
The exterior entrance features a welcoming set of steps leading to a dark front door adorned with a seasonal wreath. A wooden deck provides ample space, framed by modern wood paneling. Potted plants with vibrant foliage are positioned on either side, enhancing the outdoor appeal.
Home in Mahogany
4.98 out of 5 average rating, 269 reviews

High ceiling, relaxing and modern 2bdr new build!

Welcome to this beautiful brand new two-bedroom legal basement suite located in the desired community of Mahogany. This unit offers a separate entrance, a fully equipped kitchen with all brand new appliances, and roomy two bedrooms for you to rest and feel at home. The 9ft ceilings throughout the entire unit will leave you feeling spacious and grand. The windows were built strategically and big to maximize the natural light. We look forward to hosting you.

Guest favourite
A well-appointed kitchen features light green cabinetry, a modern white stove, and a silver kettle on the burner. The countertop is grey with subtle patterns, and the backsplash consists of glossy grey tiles. Bottles and kitchen items are neatly arranged on the shelves.
Guest suite in Northwest Calgary
4.89 out of 5 average rating, 248 reviews

Greenview, a Home Away from Home.

This cute apartment is all for you . There is a kitchen, bathroom , bedroom , office and cosy living room with a big screen TV. All designed for you to relax while away from home. Includes wifi. There is a small deck for you to sit outside in the sunshine when the weather is nice. There is a shared utility room with a washer and dryer. It’s easy to order in food or groceries . Restaurants and supermarket close by. There is lots of free street parking.

Popular amenities for Chestermere family-friendly rentals

When is the best time to visit Chestermere?

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Avg. price$134 SGD$134 SGD$118 SGD$124 SGD$139 SGD$188 SGD$210 SGD$175 SGD$147 SGD$140 SGD$124 SGD$135 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!