Holiday rentals near WinSport

We found 2,495 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

March 2026

April 2026

Find the perfect holiday rental within close proximity to WinSport. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and parking. 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 - WinSport

Showing deals for:19 June - 26 June

Exceptional

(5 reviews)

Stay Together! with Games Room & Yoga Room

Calgary

17% off

for 7 nights, 1 home

AU$630 per night

includes taxes & fees

Very good

(7 reviews)

Private bathroom, living room with projector - Basement Suite for 3

Calgary

12% off

for 7 nights, 1 home

AU$113 per night

includes taxes & fees

Exceptional

(9 reviews)

Cozy and Tastefully Furnished 1BR Guest Suite Close to Spruce Meadows SW Calgary

Calgary

8% off

for 7 nights, 1 home

AU$144 per night

includes taxes & fees

Exceptional

(33 reviews)

EXQUISITE 3BD HOUSE CLOSE TO AIRPORT, PL HOSP, DOWNTOWN, SLEEPS 7

Calgary

7% off

for 7 nights, 1 home

AU$249 per night

includes taxes & fees

Exceptional

(5 reviews)

Newly legal 2BR Basement in Seton, SE Calgary- weekly/monthly discount

Calgary

12% off

for 7 nights, 1 home

AU$108 per night

includes taxes & fees

Bedroom #2: queen bed, with large bright window.

Very good

(23 reviews)

Two bedroom unit for 5 guests in Edgemont North West of Calgary

Calgary

8% off

for 7 nights, 1 home

AU$232 per night

includes taxes & fees

Exceptional

(8 reviews)

Beautiful Calgary Home +Lake Access+BBQ, 2 Luxurious King Beds, 4 Bed+3.5 Baths

Calgary

8% off

for 7 nights, 1 home

AU$572 per night

includes taxes & fees

Exceptional

(6 reviews)

Peaceful and spacious family-friendly basement suite next to Fish Creek Park

Calgary

5% off

for 7 nights, 1 apartment

AU$191 per night

includes taxes & fees

Exceptional

(6 reviews)

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

Calgary

8% off

for 7 nights, 1 apartment

AU$230 per night

includes taxes & fees

Exceptional

(5 reviews)

1 hr to Banff – Convenient for families and group travellers.

Cochrane

8% off

for 7 nights, 1 home

AU$422 per night

includes taxes & fees

Exceptional

(5 reviews)

Southwest Cozy vibes, fast Wi-Fi – your chill Calgary escape starts here!

Calgary

8% off

for 7 nights, 1 home

AU$191 per night

includes taxes & fees

Exceptional

(5 reviews)

Funky House - Private Hot Tub - Walking Distance to Downtown

Calgary

11% off

for 7 nights, 1 home

AU$313 per night

includes taxes & fees

Wonderful

(9 reviews)

Central, Modern and Cozy 1 Bedroom Retreat in the Heart of Tuxedo

Calgary

8% off

for 7 nights, 1 apartment

AU$152 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - WinSport

Premier Host

NEWHiddenGemDiscountMovieTheatreDeckACDowntown 15'Banff 60'*Bedrooms 4x

4 bedrooms · 3 bathrooms

2BR Cozy Suite• Fireplace• Yoga Studio• FREE Banff Pass• Parking• Netflix!

2 bedrooms · 2 bathrooms

Top rated rentals - WinSport

Image of Cosmopolitan Calgary, Modern Loft

Premier Host

Home away from home

This was a lovely place to stay. Everything you could need and a short walk from lots of food options. Great for any length of stay although you’ll definitely want to stay longer.

Michelle E.

Stayed Oct 2024

Image of Creeker’s Loft-peaceful forest retreat

Home from home in an idyllic setting

Just minutes drive from Bragg Creek in the most idyllic and private setting, we couldn’t not relax and switch off! You can’t beat a ‘home from home’ feeling when you’re away, and that’s exactly how it felt. Everything had been provided in the accommodation, was spotlessly clean & a lot of thought had gone into the little touches. We wouldn’t hesitate to recommend and will return, thanks Danielle & John

Nadine D.

Stayed Aug 2023

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

More holiday ideas

Holiday homes

Holiday rentals with weekly discounts - WinSport

Showing deals for:19 June - 26 June

Stay Together! with Games Room & Yoga Room

Very bright walkout basement Close to Mountains

Private bathroom, living room with projector - Basement Suite for 3

Cozy and Tastefully Furnished 1BR Guest Suite Close to Spruce Meadows SW Calgary

Cozy Urban Retreat

EXQUISITE 3BD HOUSE CLOSE TO AIRPORT, PL HOSP, DOWNTOWN, SLEEPS 7

Modern Downtown Calgary Condo

Newly legal 2BR Basement in Seton, SE Calgary- weekly/monthly discount

Two bedroom unit for 5 guests in Edgemont North West of Calgary

Cozy 2 Bedroom Secondary suite ( basement )

Brand new High End Home in Willow Park

Cozy New Suite in South Calgary

Beautiful Calgary Home +Lake Access+BBQ, 2 Luxurious King Beds, 4 Bed+3.5 Baths

Peaceful and spacious family-friendly basement suite next to Fish Creek Park

Guest suite in Northwest Calgary

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

1 hr to Banff – Convenient for families and group travellers.

New Cozy 2 BR suite w/ king bed

Southwest Cozy vibes, fast Wi-Fi – your chill Calgary escape starts here!

Funky House - Private Hot Tub - Walking Distance to Downtown

Central, Modern and Cozy 1 Bedroom Retreat in the Heart of Tuxedo

Find spaces that suit your style

Find the best place to stay - WinSport

NEWHiddenGemDiscountMovieTheatreDeckACDowntown 15'Banff 60'*Bedrooms 4x

2BR Cozy Suite• Fireplace• Yoga Studio• FREE Banff Pass• Parking• Netflix!

The Bow Nest | Fenced Backyard | Fireplace | Pets

2 Bed rooms, 3 beds with garage for a cozy stay in Calgary

Spacious 2BR Suite | Full Kitchen & Laundry | Pet Friendly

2 BR, 2 BA Newly Renovated Condo with Pool

Top rated rentals - WinSport

Home away from home

Home from home in an idyllic setting

Peace of mind

More quality time

All the privacy of home

More for less

More holiday ideas

Holiday rentals near WinSport

Holiday rentals with weekly discounts - WinSport

Showing deals for:19 June - 26 June

Image gallery for Stay Together! with Games Room & Yoga Room

Stay Together! with Games Room & Yoga Room

Find spaces that suit your style

Find the best place to stay - WinSport

*NEW*HiddenGem*Discount*MovieTheatre*Deck*AC*Downtown 15'*Banff 60'*Bedrooms 4x

Top rated rentals - WinSport

Home away from home

Peace of mind

More quality time

All the privacy of home

More for less

More holiday ideas

NEWHiddenGemDiscountMovieTheatreDeckACDowntown 15'Banff 60'*Bedrooms 4x