Holiday rentals near Chesswood Arena
We found 3,509 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:7 Nov - 14 Nov
Image gallery for Superhouse for all!
8.48.4 out of 10 rating
Very good
(5 reviews)
Superhouse for all!
Pickering, ON
15% off
Price is £2,782
£2,782
£397 per night
includes taxes & fees
Image gallery for Walkout Basement with Private Entrance
1010 out of 10 rating
Exceptional
(5 reviews)
Walkout Basement with Private Entrance
Brampton, ON
8% off
Price is £849
£849
£121 per night
includes taxes & fees
Image gallery for Newly renovated 3 bedroom unit Richmond Hill
1010 out of 10 rating
Exceptional
(11 reviews)
Newly renovated 3 bedroom unit Richmond Hill
Richmond Hill, ON
6% off
Price is £732
£732
£105 per night
includes taxes & fees
Image gallery for Beautiful, Spacious and Good Location
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Beautiful, Spacious and Good Location
Mississauga, ON
7% off
Price is £1,488
£1,488
£213 per night
includes taxes & fees
Image gallery for Luxurious 5 bedrooms, 6 bath Custom Home
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Luxurious 5 bedrooms, 6 bath Custom Home
Richmond Hill, ON
8% off
Price is £10,818
£10,818
£1,545 per night
includes taxes & fees
Image gallery for Cottage Vibes, City Convenience
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Cottage Vibes, City Convenience
Caledon, ON
8% off
Price is £2,231
£2,231
£319 per night
includes taxes & fees
Image gallery for A Castle on 3 Acres & 17,000 sq. ft. in Brampton, ON
1010 out of 10 rating
Exceptional
(7 reviews)
A Castle on 3 Acres & 17,000 sq. ft. in Brampton, ON
Brampton, ON
15% off
Price is £9,863
£9,863
£1,409 per night
includes taxes & fees
Image gallery for Upscale Space - 5 min from Square One
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Upscale Space - 5 min from Square One
Mississauga, ON
8% off
Price is £540
£540
£77 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
(22 reviews)
5 Bedroom Countryside-Cottage King ON - 35% Winter & Long Stay Discount.
King, ON
7% off
Price is £1,666
£1,666
£238 per night
includes taxes & fees
Image gallery for 3 Bedrooms Markham Private HOME w Parking 3-6Guests
1010 out of 10 rating
Exceptional
(13 reviews)
3 Bedrooms Markham Private HOME w Parking 3-6Guests
Markham, ON
6% off
Price is £1,025
£1,025
£146 per night
includes taxes & fees
Image gallery for Stylish 2BR: w/free parking & streaming!
8.48.4 out of 10 rating
Very good
(5 reviews)
Stylish 2BR: w/free parking & streaming!
Pickering, ON
11% off
Price is £663
£663
£95 per night
includes taxes & fees
Image gallery for 2B Basement | 20% OFF | 0 Cleaning Fee | Mins to Lake | Free Parking
9.49.4 out of 10 rating
Exceptional
(11 reviews)
2B Basement | 20% OFF | 0 Cleaning Fee | Mins to Lake | Free Parking
Richmond Hill, ON
8% off
Price is £557
£557
£80 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 £578
£578
£83 per night
includes taxes & fees
Image gallery for 2 Bed 2 Bath Apartment in Mississauga near Square One
9.89.8 out of 10 rating
Exceptional
(8 reviews)
2 Bed 2 Bath Apartment in Mississauga near Square One
Mississauga, ON
7% off
Price is £718
£718
£103 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 £1,938
£1,938
£277 per night
includes taxes & fees
Image gallery for Richmond Hill Ravine Retreat
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Richmond Hill Ravine Retreat
Richmond Hill, ON
8% off
Price is £548
£548
£78 per night
includes taxes & fees
Image gallery for RedDore - 2 Bedroom Cozy Basement Suite
1010 out of 10 rating
Exceptional
(27 reviews)
RedDore - 2 Bedroom Cozy Basement Suite
Pickering, ON
7% off
Price is £711
£711
£102 per night
includes taxes & fees
Image gallery for Luxury 5Star Home away from Home
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Luxury 5Star Home away from Home
Brampton, ON
12% off
Price is £1,262
£1,262
£180 per night
includes taxes & fees
Image gallery for Modern Luxury House W/ HOT TUB
8.68.6 out of 10 rating
Excellent
(22 reviews)
Modern Luxury House W/ HOT TUB
Richmond Hill, ON
7% off
Price is £1,495
£1,495
£214 per night
includes taxes & fees
Image gallery for Spacious Beautiful House in Mississauga, 15 minutes from Toronto PRIME LOCATION!
9.49.4 out of 10 rating
Exceptional
(23 reviews)
Spacious Beautiful House in Mississauga, 15 minutes from Toronto PRIME LOCATION!
Mississauga, ON
23% off
Price is £2,111
£2,111
£302 per night
includes taxes & fees
Image gallery for Entire Basement Suite | Private Access | Clean, Comfortable, and Convenient
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Entire Basement Suite | Private Access | Clean, Comfortable, and Convenient
Richmond Hill, ON
8% off
Price is £488
£488
£70 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
(38 reviews)
2bedrooms minutes walk to Scotiabank arena, MTCC, Rogers centre
Toronto, ON
8% off
Price is £2,279
£2,279
£326 per night
includes taxes & fees
Image gallery for Luxurious open concept 2 bedroom apt on ravine, pond, central, airport, shopping
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Luxurious open concept 2 bedroom apt on ravine, pond, central, airport, shopping
Brampton, ON
7% off
Price is £644
£644
£92 per night
includes taxes & fees
Image gallery for Home in Serene Suburbia 905
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Home in Serene Suburbia 905
Mississauga, ON
8% off
Price is £1,326
£1,326
£189 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chesswood Arena
Clean 3BR/2BA Apt - Steps to Amenities!
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
GLOBALSTAY. Modern North York Condos
Sleeps 4 · 1 bedroom
6.86.8 out of 10
136 reviews(136 reviews)
Your cozy home in Richmond Hill downtown!
Sleeps 7 · 3 bedrooms · 1 bathroom
5.05.0 out of 10
2 reviews(2 reviews)
Top rated rentals - Chesswood Arena
Excellent property a short walk from the centre
1010 out of 10
Exceptionalexceptional
169 reviews(169 reviews)
Amazing - perfect honeymoon!
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value