Holiday houses in Chestermere

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Top-rated holiday rentals in Chestermere

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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.

Top Guest favourite
A modern living area features floor-to-ceiling glass windows offering views of downtown Calgary. A sleek black sofa is positioned on an area rug, accompanied by a glass coffee table. The open kitchen area is visible, highlighting contemporary appliances and cabinetry.
Condo in Beltline
4.97 out of 5 average rating, 157 reviews

City Views on 13th Ave

Welcome to one of a kind corner unit 2b+2b, 886 SQFT, with extraordinary views of downtown Calgary. This corner unit boasts floor to ceiling glass windows facing N and W facing the iconic Calgary Tower. Within walking distance to 17th, Saddle-dome. and downtown. Steps away from Calgary's trendiest restaurants and best nightlife, St James corner Pub, Proof, Ten Foot Henry, Native Tongues, Two Penny, endless pubs,17th Ave SW, Also Starbucks and yoga. studio a stone throw from front entrance.

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
A bright living area features a sectional sofa adorned with decorative pillows, complemented by a rounded coffee table. Sunlight streams through large windows, illuminating the space. A modern kitchen with bar seating is visible in the background, creating an open and inviting layout.
Condo in Beltline
4.97 out of 5 average rating, 154 reviews

BEST *Stampede* Location 1B Condo+FREE Parking!

FREE UG Secured Parking - 1 spot ***Walk Score 96*** Welcome to our modern downtown condo situated just above the famed 17th Avenue in downtown core! This stunning one-bedroom condo is absolutely perfect for working travelling people or couples seeking adventure in the heart of the city. Whether you're here to explore the city, business trip, attend the famous Stampede festival, or simply relax with someone special, this charming place has everything you need for an amazing stay! BL266105

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.

Superhost
A tranquil lake view showcases calm waters reflecting the sky with soft hues. Boats can be seen gliding across the surface, while a shoreline lined with docks and greenery provides a serene backdrop. The expansive scene highlights the peaceful atmosphere of the area.
Guest suite in Chestermere
4.8 out of 5 average rating, 76 reviews

Entire Basement suite

Welcome to our inviting 2-bedroom basement suite, ideally located just a 5-minute stroll from the glistening lakefront. Tucked away in a peaceful and serene neighborhood, this hidden gem offers the perfect blend of comfort and convenience. The suite boasts a well-appointed living area, ensuring a homely atmosphere for your stay. Whether you're here for a weekend getaway or an extended stay, our prime location ensures easy access to water activities, trails, and local eateries.

Top Guest favourite
The glamping tent is set in a forested area, featuring a wooden deck with seating arrangements. A lantern hangs from the frame, illuminating the tent's entrance. Surrounding greenery includes trees and potted plants, contributing to a serene outdoor ambiance.
Tent in Priddis
4.93 out of 5 average rating, 151 reviews

Braided Creek Luxury Glamping

Indoor - Outdoor Living at its finest. Feel at home in the luxuriously appointed glamping tent just 12 minutes from South Calgary. Private, secluded tent located on a creek with tranquil views boasting a toasty furnace, mini fridge, outdoor kitchen, hot shower, flushing toilet, power outlets. Plenty do to or nothing at all from exploring the nearby 166km of maintained trails in Bragg Creek, fishing the creek from your deck, to playing lawn games in your private 1 acre area.

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, 283 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.

Top Guest favourite
An open-concept living area is highlighted by an island kitchen featuring stainless steel appliances. A dining table is set near a window, while a comfortable seating arrangement is visible, with light fixtures illuminating the space. Decorated walls enhance the modern design.
Guesthouse in Silver Springs
5 out of 5 average rating, 329 reviews

NW ..Carriage House 800 sq ft of private luxury

Welcome to HORSEMEN HOUSE. This carriage house is detached from the main house and features high end features and fixtures for the short and longer term traveller. The 10 ft ceiling give this 800 sq ft a very spacious feeling. Located close to the U of C / Children's & Foothills hospital, and Canada Olympic Park. Very quiet neighbourhood, close to transit and includes off street parking. Easy access to Banff via the NW ring road ( Stoney Trail).

Top Guest favourite
Condo in Inglewood
4.93 out of 5 average rating, 152 reviews

Amazing View, King Bed, Trendy Neighbourhood

- Spacious 1-bedroom condo with tall ceilings - King size bed with lots of pillows - 55" TV with Apple play - Fast Wifi - Fully equipped kitchen - Underground Parking - Beautiful view of the Calgary city skyline. - Located in Inglewood, you will find local breweries, coffee shops, top restaurants, live music, and shopping - The Bow river, steps from your door! - Walking Distance to Stampede grounds - Watch the fireworks from the patio

Top Guest favourite
A modern kitchen features sleek white cabinetry and stainless-steel appliances. An expansive island with a contrasting dark base is complemented by simple bar stools. A glass light fixture hangs above, illuminating the work surfaces and the earthy tones of the wood flooring.
Condo in Inglewood
4.95 out of 5 average rating, 148 reviews

Condo in heart of Inglewood walk to DT or Stampede

This condo with a backyard is located one block from Calgary’s Riverwalk. Take a 10 minute walk to East Village to explore Calgary’s downtown or walk 15 minutes to the Stampede grounds and The Saddledome. Through the back alley, find yourself on Inglewood’s famous 9th Ave surrounded by the some of the best restaurants and breweries the city has to offer. We welcome you to use our backyard space, BBQ and propane fire pit.

Popular amenities for Chestermere holiday rentals

When is the best time to visit Chestermere?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$116 NZD$114 NZD$113 NZD$111 NZD$125 NZD$154 NZD$174 NZD$149 NZD$126 NZD$123 NZD$123 NZD$128 NZD
Avg. temp-8°C-7°C-2°C3°C7°C11°C15°C14°C9°C3°C-4°C-9°C

Frequently Asked Questions

  • What are the best places to stay in Chestermere?

    Stays near Chestermere Lake are frequently suggested for scenic views and easy access to waterfront activities. Accommodations around local parks and quiet neighborhoods also appeal to those seeking a relaxed atmosphere.

  • What are the best things to do in Chestermere with kids?

    Kids enjoy building sandcastles at lakeside beaches, playing in community parks, and trying family-friendly watersports. Seasonal events often feature crafts, games, and outdoor movie nights for young visitors.

  • What are some of the best things to do in Chestermere?

    Explore Chestermere Lake for watersports and picnicking, stroll the pathways at Anniversary Park, or tee off at Chestermere's golf course. Local shops and cafes provide a relaxed way to experience the town's atmosphere.

  • How is the weather in Chestermere?

    Chestermere experiences cold winters with temperatures around 8–31°F (-14–-1°C), and summers that range from 44–73°F (7–23°C) with moderate rainfall. Pack clothing for layering, as weather can shift quickly, especially in spring and autumn.

  • When is the best time to visit Chestermere?

    Late spring through early fall is often recommended, with milder temperatures and outdoor festivals around the lake. Winter provides opportunities for skating and other cold-weather activities if you prefer snowy landscapes.

  • What are the best places to visit in Chestermere?

    Chestermere Lake is frequently suggested for water activities and scenic sunsets, while Anniversary Park is popular for picnics and playgrounds. The local golf course draws those interested in a leisurely round amid prairie views.

  • What are some hiking trails in Chestermere?

    Chestermere has paved pathways along the lake, as well as scenic routes in Anniversary Park and within natural green areas. These trails are often used for walking, cycling, and enjoying prairie views.

  • What are some family activities we can do in Chestermere?

    Families can explore lakeside beaches, try paddleboarding, or visit local playgrounds and parks. Community centers sometimes host indoor recreation and creative programming for all ages.

  • What are some of the best day trip ideas from Chestermere?

    Explore nearby prairies, regional parks, or bustling city neighborhoods for art and shopping. Visitors sometimes head toward the Rocky Mountains or local ranches for hiking, horseback riding, or scenic drives.

  • Are there any pet friendly accommodations available in Chestermere?

    Many accommodations in Chestermere welcome pets, especially in areas near parks and walking trails. It is a good idea to check each listing’s policies to ensure your pet’s needs are met.

  • What are some local tips for visiting Chestermere?

    Locals often suggest arriving early during summer weekends to find peaceful lakeside spots. Bringing bicycles or renting paddleboards can help you enjoy the town’s trails and the water, while supporting local cafes is a favorite community tradition.

  • What is Chestermere known for?

    Chestermere is known for its large recreational lake, close-knit community, and lakeside lifestyle. The area combines water activities, outdoor trails, and a relaxed pace distinct from nearby urban centers.

  • What are the best hidden gems to explore in Chestermere?

    Explore quiet green spaces tucked behind neighborhoods, local farmers' markets, or small art installations scattered around town. Some visitors enjoy discovering lesser-known lakeshore spots perfect for early morning walks.

  • What are the best foods to try in Chestermere?

    Chestermere features locally owned restaurants with Canadian classics, international cuisine, and comforting baked goods. Popular choices often include Alberta beef dishes, fresh lake-inspired plates, and seasonal produce from nearby farms.

  • What should I bring for a trip to Chestermere?

    Pack layers for changing weather and a waterproof jacket, especially in spring or fall. Swimwear and sunscreen are useful for lake activities in summer, while winter brings a need for insulated coats, hats, and gloves.

  • What is the nightlife in Chestermere like?

    Chestermere's nightlife centers on casual pubs, local bars, and occasional live music venues. Evenings often revolve around social dining and relaxed community gatherings rather than a bustling club scene.

  • What are the most popular events or festivals in Chestermere?

    Chestermere hosts a summer water festival with boating and fireworks, as well as winter celebrations that feature skating and community gatherings. Canada Day festivities around the lake are another vibrant annual tradition.

  • Are there family friendly vacation rentals in Chestermere?

    Chestermere has a variety of vacation rentals, including homes and suites often suited for families. Look for listings with spacious living areas, kitchens, and access to parks or the lake, which can make trips with children more comfortable.

Quick stats about holiday rentals in Chestermere

  • Total holiday rentals

    Explore 120 holiday rentals in Chestermere

  • Nightly prices starting at

    Chestermere holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Chestermere holiday rentals include Wi-Fi 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!

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