Holiday rentals near Chesswood Arena
We found 3,481 holiday rentals — enter your dates for availability
Find the perfect holiday rental within easy reach of Chesswood Arena. Holiday homes provide the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Chesswood Arena
Showing deals for:26 Sept - 3 Oct
Image gallery for Deluxe Suite, Free Parking, Port Credit Lakeshore
8.08.0 out of 10 rating
Very good
(5 reviews)
Deluxe Suite, Free Parking, Port Credit Lakeshore
Mississauga, ON
8% off
Price is NZ$2,262
NZ$2,262
NZ$323 per night
includes taxes & fees
Image gallery for Walkout Basement with Private Entrance
1010 out of 10 rating
Exceptional
(6 reviews)
Walkout Basement with Private Entrance
Brampton, ON
8% off
Price is NZ$1,828
NZ$1,828
NZ$261 per night
includes taxes & fees
Image gallery for Huge Mansion loaded with all amenities for quiet enjoyment
8.08.0 out of 10 rating
Very good
(6 reviews)
Huge Mansion loaded with all amenities for quiet enjoyment
Richmond Hill, ON
7% off
Price is NZ$10,802
NZ$10,802
NZ$1,543 per night
includes taxes & fees
Image gallery for 5 Bedroom Countryside-Cottage King ON - 35% Winter & Long Stay Discount.
9.69.6 out of 10 rating
Exceptional
(20 reviews)
5 Bedroom Countryside-Cottage King ON - 35% Winter & Long Stay Discount.
King, ON
8% off
Price is NZ$3,687
NZ$3,687
NZ$527 per night
includes taxes & fees
Image gallery for Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
1010 out of 10 rating
Exceptional
(12 reviews)
Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
Aurora, ON
5% off
Price is NZ$1,290
NZ$1,290
NZ$184 per night
includes taxes & fees
Image gallery for Newly Renovated LakeView Retreat
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Newly Renovated LakeView Retreat
Mississauga, ON
8% off
Price is NZ$1,250
NZ$1,250
NZ$179 per night
includes taxes & fees
Image gallery for 2bedrooms minutes walk to Scotiabank arena, MTCC, Rogers centre
8.48.4 out of 10 rating
Very good
(37 reviews)
2bedrooms minutes walk to Scotiabank arena, MTCC, Rogers centre
Toronto, ON
8% off
Price is NZ$6,730
NZ$6,730
NZ$961 per night
includes taxes & fees
Image gallery for Home in Serene Suburbia 905
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Home in Serene Suburbia 905
Mississauga, ON
8% off
Price is NZ$2,852
NZ$2,852
NZ$407 per night
includes taxes & fees
Image gallery for Luxury Apartment Living in an Elite Neighborhood
1010 out of 10 rating
Exceptional
(10 reviews)
Luxury Apartment Living in an Elite Neighborhood
Mississauga, ON
8% off
Price is NZ$1,438
NZ$1,438
NZ$205 per night
includes taxes & fees
Image gallery for Spotless & Spacious 2BR/2BA Comfortably Sleeps 6
1010 out of 10 rating
Exceptional
(16 reviews)
Spotless & Spacious 2BR/2BA Comfortably Sleeps 6
Mississauga, ON
8% off
Price is NZ$2,471
NZ$2,471
NZ$353 per night
includes taxes & fees
Image gallery for Downtown Toronto near CN Tower, MTCC, Rogers Center , Union station
8.68.6 out of 10 rating
Excellent
(40 reviews)
Downtown Toronto near CN Tower, MTCC, Rogers Center , Union station
Toronto, ON
8% off
Price is NZ$4,997
NZ$4,997
NZ$714 per night
includes taxes & fees
Image gallery for 1King 1Queen 1Twin Beds/CN TowerView/Luxury Suite
8.48.4 out of 10 rating
Very good
(37 reviews)
1King 1Queen 1Twin Beds/CN TowerView/Luxury Suite
Toronto, ON
8% off
Price is NZ$3,572
NZ$3,572
NZ$510 per night
includes taxes & fees
Image gallery for New Private Spacious & Modern Apartment near Square One and Downtown Mississauga
1010 out of 10 rating
Exceptional
(5 reviews)
New Private Spacious & Modern Apartment near Square One and Downtown Mississauga
Mississauga, ON
8% off
Price is NZ$2,056
NZ$2,056
NZ$294 per night
includes taxes & fees
Image gallery for Luxury Waterfront Suite
8.68.6 out of 10 rating
Excellent
(24 reviews)
Luxury Waterfront Suite
Toronto, ON
9% off
Price is NZ$5,858
NZ$5,858
NZ$837 per night
includes taxes & fees
Image gallery for Comfy private and quiet retreat in the center of town.
9.09.0 out of 10 rating
Wonderful
(14 reviews)
Comfy private and quiet retreat in the center of town.
Aurora, ON
8% off
Price is NZ$1,097
NZ$1,097
NZ$157 per night
includes taxes & fees
Image gallery for Beautiful, Spacious and Good Location
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Beautiful, Spacious and Good Location
Mississauga, ON
8% off
Price is NZ$3,209
NZ$3,209
NZ$458 per night
includes taxes & fees
Image gallery for Executive 2 Beds by Rogers Centre, Ripley’s Aquarium & Free Parking
8.08.0 out of 10 rating
Very good
(37 reviews)
Executive 2 Beds by Rogers Centre, Ripley’s Aquarium & Free Parking
Toronto, ON
8% off
Price is NZ$4,953
NZ$4,953
NZ$708 per night
includes taxes & fees
Image gallery for Modern Luxury House W/ HOT TUB
8.48.4 out of 10 rating
Very good
(20 reviews)
Modern Luxury House W/ HOT TUB
Richmond Hill, ON
7% off
Price is NZ$4,317
NZ$4,317
NZ$617 per night
includes taxes & fees
Image gallery for Port Credit - Mineola Cottage
1010 out of 10 rating
Exceptional
(15 reviews)
Port Credit - Mineola Cottage
Mississauga, ON
9% off
Price is NZ$2,243
NZ$2,243
NZ$320 per night
includes taxes & fees
Image gallery for Luxury Guest House In King City
9.29.2 out of 10 rating
Wonderful
(22 reviews)
Luxury Guest House In King City
King, ON
8% off
Price is NZ$4,170
NZ$4,170
NZ$596 per night
includes taxes & fees
Image gallery for Dazzling Modern Home Next to Beach & Go Station
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Dazzling Modern Home Next to Beach & Go Station
Pickering, ON
8% off
Price is NZ$4,899
NZ$4,899
NZ$700 per night
includes taxes & fees
Image gallery for 3 BED/2 BATH cozy BUNGALOW in prestigious neighborhood of Richmond Hill- sleep 6
9.69.6 out of 10 rating
Exceptional
(31 reviews)
3 BED/2 BATH cozy BUNGALOW in prestigious neighborhood of Richmond Hill- sleep 6
Richmond Hill, ON
8% off
Price is NZ$3,953
NZ$3,953
NZ$565 per night
includes taxes & fees
Image gallery for #1 Best Deal in Brampton
9.69.6 out of 10 rating
Exceptional
(5 reviews)
#1 Best Deal in Brampton
Caledon, ON
7% off
Price is NZ$3,202
NZ$3,202
NZ$457 per night
includes taxes & fees
Image gallery for Cozy comfort unit in Richmond Hill. Your home away from home!
1010 out of 10 rating
Exceptional
(10 reviews)
Cozy comfort unit in Richmond Hill. Your home away from home!
Richmond Hill, ON
11% off
Price is NZ$1,798
NZ$1,798
NZ$257 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chesswood Arena
GLOBALSTAY. Modern North York Condos
Sleeps 4 · 1 bedroom
7.07.0 out of 10
Goodgood
129 reviews(129 reviews)
Clean 3BR/2BA Apt - Steps to Amenities!
Sleeps 7 · 3 bedrooms · 2 bathrooms
Your cozy home in Richmond Hill downtown!
Sleeps 7 · 3 bedrooms · 1 bathroom
4.04.0 out of 10
1 review(1 review)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value