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Estates in Collingwood and Apartments - Holiday Lettings - Holiday Rentals Collingwood

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72 Holiday homes

Holiday apartment in Collingwood

Collingwood apartment

  • 1 bedroom
  • sleeps 6
  • 2 bathrooms

from £101 / night

£707 / week

1 / 17

Ski apartment to rent in Collingwood

Collingwood apartment

  • 3 bedrooms
  • sleeps 6
  • 1 bathroom
  • Wi-Fi available

from £169 / night

£875 / week

1 / 11

Holiday apartment in Collingwood

Collingwood apartment

  • sleeps 2
  • 1 bathroom

from £114 / night

£797 / week

1 / 25

Holiday apartment rental

Collingwood apartment

  • 3 bedrooms
  • sleeps 8
  • 2 bathrooms

from £101 / night

£707 / week

1 / 26

Collingwood holiday hotel apartment rental

Collingwood hotel apartment

  • 1 bedroom
  • sleeps 4
  • 2 bathrooms
  • Wi-Fi available

from £132 / night

£921 / week

1 / 8

Ski condo to rent in Collingwood

Collingwood condo

  • 1 bedroom
  • sleeps 4
  • 1 bathroom
  • Wi-Fi available

from £152 / night

£808 / week

1 / 16

Holiday condo with shared pool in Collingwood

Collingwood condo

  • 2 bedrooms
  • sleeps 6
  • 2 bathrooms
  • Wi-Fi available

from £148 / night

£1,037 / week

1 / 8

Holiday home letting

Collingwood house

  • 2 bedrooms
  • sleeps 4
  • 2 bathrooms

from £135 / night

£943 / week

1 / 20

Collingwood ski cottage to rent.

Collingwood cottage

  • 1 bedroom
  • sleeps 4
  • 1 bathroom
  • Wi-Fi available

from £105 / night

£741 - £929 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday chalet in Wasaga Beach

Wasaga Beach chalet

  • 5 bedrooms
  • sleeps 10
  • 4 bathrooms
  • Wi-Fi available

from £132 / night

£939 / week

1 / 12

Holiday cottage in Blue Mountains

Blue Mountains cottage

  • 4 bedrooms
  • sleeps 5
  • 5 bathrooms

from £150 / night

£1,047 / week

1 / 10

Penetanguishene holiday cottage rental

Penetanguishene cottage

  • 4 bedrooms
  • sleeps 8
  • 2 bathrooms

from £202 / night

£2,356 / week

1 / 18

Holiday home in Blue Mountains

Blue Mountains house

  • 5 bedrooms
  • sleeps 14
  • 4 bathrooms
  • Wi-Fi available

from £225 / night

£1,571 / week

1 / 45

Wasaga Beach holiday cottage rental

Wasaga Beach cottage

  • 2 bedrooms
  • sleeps 8
  • 1 bathroom
  • Wi-Fi available

from £73 / night

£513 - £635 / week

1 / 16

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 2 bedrooms
  • sleeps 8
  • 1 bathroom
  • Wi-Fi available

from £75 / night

£519 - £691 / week

1 / 11

Holiday chalet in Craigleith

Craigleith chalet

  • 8 bedrooms
  • sleeps 20
  • 2 bathrooms

from £471 / night

£1,683 - £2,625 / week

1 / 8

Tiny holiday cottage rental

Tiny cottage

  • 2 bedrooms
  • sleeps 6
  • 1 bathroom

from £135 / night

£875 - £1,064 / week

1 / 26

Singhampton ski cottage to rent.

Singhampton cottage

  • 3 bedrooms
  • sleeps 15
  • 2 bathrooms
  • Wi-Fi available

from £313 / night

£2,188 - £3,342 / week

1 / 27

Cottage rental in Singhampton

Singhampton cottage

  • 3 bedrooms
  • sleeps 9
  • 2 bathrooms
  • Wi-Fi available

from £336 / night

£1,789 - £1,907 / week

1 / 26

Holiday lodge in Singhampton

Singhampton lodge

  • 1 bedroom
  • sleeps 4

from £80 / night

£457 / week

1 / 16

Holiday townhouse in Blue Mountains

Blue Mountains townhouse

  • 5 bedrooms
  • sleeps 10
  • 3 bathrooms

from £397 / night

£2,019 / week

1 / 15

Log cabin rental in Wasaga Beach

Wasaga Beach log cabin

  • 2 bedrooms
  • sleeps 5
  • 1 bathroom
  • Wi-Fi available

from £194 / night

£875 / week

1 / 13

Holiday home in Wasaga Beach

Wasaga Beach house

  • 4 bedrooms
  • sleeps 10
  • 2 bathrooms
  • Wi-Fi available

from £113 / night

£786 / week

1 / 4

Holiday chalet in Craigleith

Craigleith chalet

  • 3 bedrooms
  • sleeps 8
  • 2 bathrooms
  • Wi-Fi available

from £270 / night

£1,616 / week

1 / 36

Ski chalet to rent in Blue Mountains

Blue Mountains chalet

  • 4 bedrooms
  • sleeps 12
  • 2 bathrooms
  • Wi-Fi available

from £320 / night

£2,019 / week

1 / 24

Holiday home in Thornbury

Thornbury house

  • 6 bedrooms
  • sleeps 15
  • 4 bathrooms
  • Wi-Fi available

from £572 / night

£4,005 / week

1 / 11

Holiday lodge in Singhampton

Singhampton lodge

  • 1 bedroom
  • sleeps 6
  • 1 bathroom

from £87 / night

£562 / week

1 / 18

Ski home to rent in Thornbury

Thornbury house

  • 3 bedrooms
  • sleeps 5
  • 2 bathrooms
  • Wi-Fi available

from £128 / night

£895 / week

1 / 30

Holiday home in Craigleith

Craigleith house

  • 5 bedrooms
  • sleeps 12
  • 3 bathrooms

from £673 / night

£3,029 - £3,264 / week

1 / 9

Craigleith ski bungalow to rent.

Craigleith bungalow

  • 2 bedrooms
  • sleeps 6
  • 2 bathrooms
  • Wi-Fi available

from £202 / night

£1,010 - £1,245 / week

1 / 13

Holiday home in Kimberley

Kimberley house

  • 8 bedrooms
  • sleeps 16
  • 8 bathrooms

from £640 / night

£3,769 - £5,889 / week

1 / 28

Holiday barn in Flesherton

Flesherton barn

  • 3 bedrooms
  • sleeps 6
  • 4 bathrooms

from £461 / night

£2,420 - £2,774 / week

1 / 8

Holiday villa in Flesherton

Flesherton villa

  • 13 bedrooms
  • sleeps 16
  • 11 bathrooms
  • Wi-Fi available

from £2,659 / night

£13,957 - £20,846 / week

1 / 24

Stayner holiday home rental

Stayner house

  • 5 bedrooms
  • sleeps 35
  • 3 bathrooms
  • Wi-Fi available

from £976 / night

£6,831 / week

1 / 53

Wasaga Beach holiday cottage rental

Wasaga Beach cottage

  • 2 bedrooms
  • sleeps 4
  • 1 bathroom
  • Wi-Fi available

from £105 / night

£690 - £1,004 / week

1 / 17

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 2 bedrooms
  • sleeps 4
  • 1 bathroom
  • Wi-Fi available

from £99 / night

£657 - £941 / week

1 / 16

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 1 bedroom
  • sleeps 2
  • 1 bathroom
  • Wi-Fi available

from £72 / night

£478 - £690 / week

1 / 13

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 2 bedrooms
  • sleeps 4
  • 1 bathroom
  • Wi-Fi available

from £99 / night

£657 - £941 / week

1 / 16

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 1 bedroom
  • sleeps 3
  • 1 bathroom
  • Wi-Fi available

from £79 / night

£526 - £758 / week

1 / 13

Holiday cottage in Wasaga Beach

Wasaga Beach cottage

  • 3 bedrooms
  • sleeps 10
  • 1 bathroom
  • Wi-Fi available

from £127 / night

£747 - £1,606 / week

1 / 13

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Collingwood holidays

As the gateway to the Blue Mountain ski resort, Collingwood and its pretty lakeside location has become a mecca for Toronto city dwellers looking to get back to nature.

Once a proud shipbuilding town, Collingwood is the springboard for the Niagara Escarpment where you’ll find outdoor pursuits to keep you busy throughout the year. And the best part? Holiday Lettings has a Collingwood property for your holiday needs!

About Collingwood

Located at the southern end of Georgian Bay in Simcoe County, Ontario, Collingwood was declared a town in 1858 (nine years before it became part of the Dominion of Canada).

Named after Lord Nelson’s second in command during the Battle of Trafalgar, Admiral Lord Cuthbert Collingwood, the area was once home to the Iroquoian Petun nation who built settlements around the Niagara Escarpment.

The first steel-clad ship built in Canada, the Huronic, was launched from Collingwood in 1901 with the shipyards going on to produce ships for the Royal Canadian Navy while employing 10% of the town's population. You can still see remnaants of the ship-building days around the towns.

Today, tourism and recreation are seen as the way forward for Collingwood, with the Ontario Tourist Board going all out to promote the region as a holiday wonderland.

What to do

One of Eastern Canada’s premier all-season resorts, Blue Mountain, is right on your doorstep with its dozens of ski slopes built around a picturesque alpine ski through village. Ontario’s largest ski destination also comes alive in the summer, with a championship golf course, mountain biking, and its own private beach.

For fantastic views, take a walk up to Millennium Overlook Park where you can look down on Collingwood while watching colourful sailboats leaving the historic Harbor.

Visit the nearby Scenic Caves for a day of adventure exploring the ancient cracks and crevices.

Top Collingwood travel tips

If you’re looking to save some money while visiting the Blue Mountain Resort, consider staying in Collingwood where Holiday Lettings has plenty of holiday rentals to match any budget.

For the best beach, head east to the town of Wasaga where you’ll find the world’s longest freshwater beach. The gently sloping sandy beach is perfect for families with young children and an excellent location to go wind or kite surfing.

Collingwood may not be on the mountain or adjacent to the beach, but it does take the sting out of resort prices. With a revitalised historic downtown full of bars, eateries, and trendy shops, there’s always something to do when you’re not on the beach or flying down the slopes.

Pick your Holiday Lettings Collingwood holiday rental today and start your next adventure.

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