Chestermere holiday rentals

We found 1,046 holiday rentals — enter your dates for availability
Discover a selection of 43 homes, 11 apartments and other holiday rentals in Chestermere that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include air conditioning and a pool. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Chestermere

Showing deals for:25 Dec - 1 Jan

Living area
Dining
Room
Private kitchen
Wonderful
(5 reviews)

Bright & Cozy 2-Bedroom Basement Suite

Conrich

7% off
S$1,104
for 7 nights, 1 home
S$158 per night
includes taxes & fees
Bright & Cozy 2-Bedroom Basement Suite
Living area
Private kitchen
Room
Dining
Exceptional
(6 reviews)

Renovated 3BR Home | A/C | Double Garage | 10 Min to Spruce Meadows

Calgary

8% off
S$3,598
for 7 nights, 1 home
S$514 per night
includes taxes & fees
Renovated 3BR Home | A/C | Double Garage | 10 Min to Spruce Meadows
Interior
Private kitchen
Living area
Property grounds
Wonderful
(5 reviews)

Cozy Pet Friendly Apartment in SE Calgary - Near South Health Campus!

Calgary

8% off
S$1,012
for 7 nights, 1 apartment
S$145 per night
includes taxes & fees
Cozy Pet Friendly Apartment in SE Calgary - Near South Health Campus!
Living area
Interior
Private kitchen
Room
Exceptional
(11 reviews)

Cozy entire 2 bedroom apartment located in the heart of Mahogany. Pet friendly.

Calgary

7% off
S$958
for 7 nights, 1 apartment
S$137 per night
includes taxes & fees
Cozy entire 2 bedroom apartment located in the heart of Mahogany. Pet friendly.
Interior
Private kitchen
Interior
Interior
Exceptional
(10 reviews)

Cozy 2 bedroom suite

Calgary

8% off
S$1,155
for 7 nights, 1 home
S$165 per night
includes taxes & fees
Cozy 2 bedroom suite
Dining
Interior
Living area
Interior
Exceptional
(9 reviews)

City Views | Walk to Calgary Tower & Stampede

Calgary

8% off
S$1,218
for 7 nights, 1 apartment
S$174 per night
includes taxes & fees
City Views | Walk to Calgary Tower & Stampede
Private entrance at the back for easy and secure access
Spacious living area with smart TV and seating
Dining and workspace area perfect for meals or work
DSC_0931
Excellent
(6 reviews)

2 BR Suite YYC Airport & Downtown, UofC, SAIT - 4324 – DN

Calgary

7% off
S$829
for 7 nights, 1 home
S$118 per night
includes taxes & fees
2 BR Suite YYC Airport & Downtown, UofC, SAIT - 4324 – DN
Room
Take a nice stroll around the block and see all the beautiful gardens :)
Interior
Your own private parking space with sitting area
Exceptional
(72 reviews)

Cozy Apartment Above Garage in Calgary SE

Calgary

8% off
S$889
for 7 nights, 1 apartment
S$127 per night
includes taxes & fees
Cozy Apartment Above Garage in Calgary SE
Living Room
Living Room
Bedroom
Miscellaneous
Exceptional
(7 reviews)

1 Bed + 1 Bath Riverside Bliss Condo In Downtown

Calgary

14% off
S$1,390
for 7 nights, 1 apartment
S$199 per night
includes taxes & fees
1 Bed + 1 Bath Riverside Bliss Condo In Downtown
Outdoor spa tub
Living area
Exterior
Room
Exceptional
(6 reviews)

Funky House - Private Hot Tub - Walking Distance to Downtown

Calgary

11% off
S$1,936
for 7 nights, 1 home
S$277 per night
includes taxes & fees
Funky House - Private Hot Tub - Walking Distance to Downtown
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting friendly Chestermere

The lake and beaches create a pretty picture of Chestermere. This welcoming and walkable city entices travellers with its restaurants and shopping. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Chestermere

Are you hoping to find attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Chestermere a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Calgary Zoo (8.9 mi / 14.3 km)
  • Stampede Park (10.1 mi / 16.2 km)
  • Heritage Park Historical Village (12.9 mi / 20.8 km)
  • Heritage Pointe Golf Course (16.1 mi / 25.9 km)
  • Canada Olympic Park (17.2 mi / 27.7 km)
  • Fox Hollow Golf Course (9.4 mi / 15.2 km)

Exploring the natural landscape of Chestermere

Whether you're an outdoor enthusiast or just want to take in the scenery, Chestermere is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Bow River (10 mi / 16 km)
  • Prince's Island Park (10.7 mi / 17.3 km)
  • Stanley Park (11 mi / 17.6 km)
  • Sandy Beach Park (11.9 mi / 19.2 km)
  • Nose Hill Park (13.2 mi / 21.3 km)
  • Bowness Park (17.9 mi / 28.8 km)

Transport options to and around Chestermere

The nearest airport is in Calgary International Airport (YYC), located 9.8 mi (15.8 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Chestermere?
The most in-demand types of holiday rentals in Chestermere are houses. Looking for something different? Vrbo has a variety of options to match the diverse needs of our guests, so you'll see holiday homes in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — find yours today.
How much does it cost to rent a holiday rental in Chestermere?
The average price for a holiday home in Chestermere can vary based on factors including season, length of stay and property type. Whether you'd like a sprawling villa with lots of space or an apartment ideal for just you and the kids, just add your travel dates to find some great-value stays.
How much does it cost to rent a beach house in Chestermere?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Enter your Chestermere travel dates to view your available options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday rentals in Chestermere?
With nine properties that welcome four-legged guests, your furry best friend can join in the fun on your Chestermere break. Use our filter tool to browse our pet-friendly holiday rentals and find a pad that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Chestermere?
Mark the "pool" box in our handy filter tool and take your pick of three houses with private pools in Chestermere on Vrbo. Gentle soak, ball games or noodle joust? How you spend your leisure time is up to you when your holiday home has its own pool.
What are popular rental amenities in Chestermere?
The most popular rental amenities people look for in Chestermere include a beach view, a lake view and mountain views. Whether you're hitting the road with family, pals or even pets, Vrbo holiday rentals include the best amenities for making new memories with your loved ones.
Are there large group holiday rentals in Chestermere?
You'll discover two properties in Chestermere that can accommodate a group of 10 or more guests. Whether you're organising a trip with the family or a special event like a birthday party, there's enough space to get your group together under one roof.
Are there holiday rentals in Chestermere that welcome kids?
Gather the whole crew for the adventure of a lifetime in Chestermere at one of our nine family-friendly holiday homes. Many of these stays offer conveniences that are ideal for trips with the kids, including laundry facilities, bunk beds and swimming pools. Simply check the "Properties good for families" filter and select your favourite.
What are the top attractions for families in Chestermere?
Keeping the kids entertained during your stay in Chestermere is a cinch with these family-friendly attractions:
  • Calgary Zoo
  • Aero Space Museum of Calgary
  • Inglewood Bird Sanctuary
Are there holiday rentals with WiFi in Chestermere?
Whether you'd like to keep up to date with the news, send a few emails or update your social media, there are five holiday homes with WiFi in Chestermere. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Chestermere?
Chestermere has five holiday rentals where you'll be able to relax in air-conditioned comfort. To locate a stay on Vrbo that comes with this amenity, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Chestermere?
The minimum required age is usually 16, 18 or 21. It can differ across properties on Vrbo, so check the rules of your chosen Chestermere holiday home before booking.
How long can I rent a holiday rental in Chestermere for?
It's really down to the Chestermere property. To see all available options offering extended stays, simply enter your dates and number of people into the Vrbo search page. Enjoy having the entire property to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and outdoor spaces where the kids can play. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.

More holiday ideas