Houses Under $500K for Rent in Collingwood, ON | Square Yards Canada

30 Photos

27 Conservation Way, Simcoe, ON , MLS #S13609436 , Image - 1

27 Conservation Way Collingwood, Simcoe, ON MLS® S13609436

Residential Condo & Other (Condo Townhouse)

$16000.0

3 Beds
4 Baths
1200-1399 sq-ft

Price listed of $16,000 is for ski season from December 1, 2026-March 31, 2027. Also available from September 15, 2026 to April 15, 2027. Located in o

26 Photos

6 Alpine Court, Simcoe, ON , MLS #S13175368 , Image - 1

6 Alpine Court Collingwood, Simcoe, ON MLS® S13175368

Residential Freehold (Detached)

$6400.0

Reduced by 14.7%

4 Beds
3 Baths
3500-5000 sq-ft

Nestled on a prestigious cul-de-sac, this beautifully crafted bungalow is a rare blend of luxury, space, and privacy. Surrounded by mature trees, two

15 Photos

107 Ellen Lane, Simcoe, ON , MLS #S13612786 , Image - 1

Unit-4, 107 Ellen Lane Collingwood, Simcoe, ON MLS® S13612786

Residential Condo & Other (Condo Townhouse)

$2800.0

2 Beds
2 Baths
1000-1199 sq-ft

Seasonal Lease Available for Ski Season for $2800/mo + utilities, or starting Oct 1st through Apr 30th. NOTE: Price is reduced to $2500/mo + utilities

26 Photos

316 Hume Street, Simcoe, ON , MLS #S13582888 , Image - 1

316 Hume Street Collingwood, Simcoe, ON MLS® S13582888

Residential Freehold (Detached)

$3500.0

2 Beds
1 Baths
700-1100 sq-ft

3-4 Month Winter Seasonal Lease (Utilities, High-Speed Internet & Snow Removal Included) Enjoy the perfect winter getaway in this newly renovated, ful

40 Photos

5 Harbour Street, Simcoe, ON , MLS #S13570942 , Image - 1

Unit-1, 5 Harbour Street Collingwood, Simcoe, ON MLS® S13570942

Residential Condo & Other (Condo Townhouse)

$2500.0

3 Beds
3 Baths
1400-1599 sq-ft

ANNUAL LEASE. Harbourside IV spacious END UNIT townhome approx. 1500 sq feet with 3 bedrooms and 2.5 bathrooms. Fantastic location in the west end of

15 Photos

4 Kimberly Lane

Unit-325, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® S13605756

Residential Condo & Other (Condo Apartment)

$2250.0

1 +1 Beds
1 Baths
700-799 sq-ft

Welcome to Royal Windsor Condos at Balmoral Village-Collingwood's premier 4-season lifestyle address! This bright and spacious 1+1 Bedroom, 1 Bath Pri

41 Photos

12 Robbie Way, Simcoe, ON , MLS #S13608516 , Image - 1

12 Robbie Way Collingwood, Simcoe, ON MLS® S13608516

Residential Freehold (Att/Row/Townhouse)

$5500.0

2 +1 Beds
4 Baths
2000-2500 sq-ft

Seasonal Furnished Executive Rental. Rate is per month plus deposits. Please contact for availability for the season you wish to stay, in this stunnin

25 Photos

8 Robbie Way, Simcoe, ON , MLS #S12946402 , Image - 1

8 Robbie Way Collingwood, Simcoe, ON MLS® S12946402

Residential Freehold (Att/Row/Townhouse)

$4000.0

Reduced by 11.1%

3 +1 Beds
4 Baths
1500-2000 sq-ft

Set against protected green space and the Cranberry Golf Course, this fully furnished executive townhome showcases designer furnishings, peaceful esca

28 Photos

57 Green Briar Drive, Simcoe, ON , MLS #S13433578 , Image - 1

57 Green Briar Drive Collingwood, Simcoe, ON MLS® S13433578

Residential Condo & Other (Condo Townhouse)

$2500.0

2 Beds
3 Baths
1000-1199 sq-ft

Welcome to 57 Green Briar Drive, a beautifully furnished 2-bedroom, 2.5-bath townhouse in the sought-afterCranberry Golf community. This peaceful, fam

32 Photos

12 MITCHELL Avenue, Simcoe, ON , MLS #S13499736 , Image - 1

12 MITCHELL Avenue Collingwood, Simcoe, ON MLS® S13499736

Residential Freehold (Detached)

$3000.0

3 Beds
3 Baths
1100-1500 sq-ft

This modern yet cozy open-concept home of over 1,300 sq ft has everything you need! An open foyer lets light in on both levels and a grey-stained oak

31 Photos

46 Barker Boulevard, Simcoe, ON , MLS #S13596538 , Image - 1

Unit-13, 46 Barker Boulevard Collingwood, Simcoe, ON MLS® S13596538

Residential Condo & Other (Condo Townhouse)

$2875.0

2 Beds
2 Baths
1200-1399 sq-ft

Ski Season Rental: Located in The Links, this lovely raised bungalow is central to all major Collingwood and area ski clubs. Ski Season rental - Avail

44 Photos

24 Ramblings Way

Unit-905, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S13238946

Residential Condo & Other (Condo Apartment)

$3500.0

Reduced by 6.7%

2 Beds
2 Baths
1000-1199 sq-ft

EXECUTIVE RENTAL WITH GORGEOUS WATER VIEWS located in the Bayview Tower at the gated community of Rupert's Landing. Enjoy stunning views of the Bay a

21 Photos

329 MARINERS Way, Simcoe, ON , MLS #S13603504 , Image - 1

329 MARINERS Way Collingwood, Simcoe, ON MLS® S13603504

Residential Condo & Other (Condo Townhouse)

$3000.0

2 +0 Beds
2 Baths
800-899 sq-ft

Welcome to Lighthouse Point, one of Collingwood's premier waterfront communities, available for the full ski season (flexible dates). Dec-March is $12

29 Photos

398 Mariners Way, Simcoe, ON , MLS #S13602374 , Image - 1

Unit-4, 398 Mariners Way Collingwood, Simcoe, ON MLS® S13602374

Residential Condo & Other (Condo Townhouse)

$12000.0

3 Beds
2 Baths
1200-1399 sq-ft

Lighthouse Point 3 bdrm 2 bath ground floor condo with garage in Collingwood, Ontario, is just minutes to all major ski resorts: Blue Mountains, Osler

23 Photos

5 Spooner Crescent, Simcoe, ON , MLS #S13494610 , Image - 1

Unit-210, 5 Spooner Crescent Collingwood, Simcoe, ON MLS® S13494610

Residential Condo & Other (Condo Apartment)

$2450.0

2 Beds
2 Baths
1000-1199 sq-ft

Discover Your Dream Retreat in Collingwood Near Blue Mountain & Georgian Bay! Nestled in the Scenic Blue Fairview Development on Cranberry Golf Course

20 Photos

871 SUNCREST Circle, Simcoe, ON , MLS #S13596810 , Image - 1

871 SUNCREST Circle Collingwood, Simcoe, ON MLS® S13596810

Residential Condo & Other (Condo Apartment)

$3250.0

3 +0 Beds
2 Baths
1400-1599 sq-ft

FALL AND WINTER SEASON RENTAL IN LIGHTHOUSE POINT! This stunning ground floor waterfront unit in highly sought-after Lighthouse Point checks all the b

30 Photos

7 ANCHORAGE Crescent, Simcoe, ON , MLS #S13593736 , Image - 1

Unit-108, 7 ANCHORAGE Crescent Collingwood, Simcoe, ON MLS® S13593736

Residential Condo & Other (Condo Townhouse)

$2200.0

2 +0 Beds
2 Baths
900-999 sq-ft

ANNUAL LEASE - Beautifully furnished ground floor unit available for annual rental in the Wyldewood Cove. This waterfront community features a year-ro

47 Photos

4 Holly Court, Simcoe, ON , MLS #S13593670 , Image - 1

4 Holly Court Collingwood, Simcoe, ON MLS® S13593670

Residential Freehold (Detached)

$14000.0

3 +2 Beds
4 Baths
2000-2500 sq-ft

Welcome to 4 Holly Court, an exceptional luxury retreat available for the 2026 ski season at $14,000 per month, utilities in addition.Set on a spectac

45 Photos

4 Kimberley Lane

Unit-106, 4 Kimberley Lane Collingwood, Simcoe, ON MLS® S13561390

Residential Condo & Other (Condo Apartment)

$2600.0

2 Beds
2 Baths
1000-1199 sq-ft

Ground Floor of one of Collingwood's newest buildings. Unfurnished annual rental in the Royal Windsor building. Step outside from your private terrace

37 Photos

24 Ramblings Way

Unit-PH 1003, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S13580992

Residential Condo & Other (Condo Apartment)

$13900.0

2 Beds
2 Baths
2000-2249 sq-ft

Arguably THE best view in Collingwood with stunning views toward Collingwood Terminals and beyond as well as toward Blue Mountain and the ski slopes.

25 Photos

7 Willow Street, Simcoe, ON , MLS #S13527298 , Image - 1

7 Willow Street Collingwood, Simcoe, ON MLS® S13527298

Residential Freehold (Detached)

$2000.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to this inviting 2-bedroom, 1-bath basement apartment in the heart of Collingwood. Featuring spacious bedrooms and a functional layout, this p

17 Photos

435 Napier Street, Simcoe, ON , MLS #S13585880 , Image - 1

Unit-B, 435 Napier Street Collingwood, Simcoe, ON MLS® S13585880

Residential Freehold (Detached)

$1950.0

1 Beds
1 Baths
700-1100 sq-ft

Bright and clean one bedroom unit. Fully detached unit with a private hot tub and a large yard. Can be rented in conjunction with a three bedroom home

25 Photos

435 Napier Street, Simcoe, ON , MLS #S13585872 , Image - 1

Unit-A, 435 Napier Street Collingwood, Simcoe, ON MLS® S13585872

Residential Freehold (Detached)

$2600.0

3 Beds
2 Baths
1500-2000 sq-ft

Enjoy your own garden oasis steps from downtown Collingwood. Professionally renovated home features three bedrooms, two full bathrooms, a spacious liv

13 Photos

7708 Poplar Side Road, Simcoe, ON , MLS #S13583260 , Image - 1

Unit-1, 7708 Poplar Side Road Collingwood, Simcoe, ON MLS® S13583260

Residential Freehold (Fourplex)

$2350.0

2 Beds
2 Baths
700-1100 sq-ft

BRAND NEW 4 PLEX UNIT! Be the first to live in this 2-bedroom, 2-bathroom ground-level unit offering a spacious and functional open-concept layout. Fe

21 Photos

550 Oxbow Crescent, Simcoe, ON , MLS #S13576000 , Image - 1

550 Oxbow Crescent Collingwood, Simcoe, ON MLS® S13576000

Residential Condo & Other (Condo Townhouse)

$3500.0

3 Beds
3 Baths
1400-1599 sq-ft

Immaculate and tastefully fully renovated spacious 3 Bed condo for you to enjoy Ski Season including Christmas & New Year close to all private clubs a

36 Photos

4 Kimberly Lane

Unit-515, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® S13550452

Residential Condo & Other (Condo Apartment)

$3000.0

2 Beds
2 Baths
1000-1199 sq-ft

FURNISHED ANNUAL RENTAL - Ready for Immediate Move-In! Welcome to refined living at the Royal Windsor condos in Balmoral Village. This 5th-floor Vicer

37 Photos

89 Georgian Manor Drive, Simcoe, ON , MLS #S12692518 , Image - 1

89 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S12692518

Residential Freehold (Detached)

$5500.0

3 Beds
2 Baths
1100-1500 sq-ft

A rare opportunity to lease a true beachfront retreat on the shores of Georgian Bay! Available for August, September & October 2026, this exceptional

46 Photos

435 Napier Street, Simcoe, ON , MLS #S13501748 , Image - 1

435 Napier Street Collingwood, Simcoe, ON MLS® S13501748

Residential Freehold (Detached)

$3990.0

Reduced by 7.1%

4 Beds
3 Baths
1500-2000 sq-ft

Enjoy your own garden oasis steps from downtown Collingwood. Professionally renovated home features three bedrooms, two full bathrooms, a spacious liv

32 Photos

194 Escarpment Crescent, Simcoe, ON , MLS #S13490408 , Image - 1

194 Escarpment Crescent Collingwood, Simcoe, ON MLS® S13490408

Residential Condo & Other (Condo Townhouse)

$4000.0

3 Beds
2 Baths
1200-1399 sq-ft

SEASONAL FALL/WINTER LEASE - COMPLETELY RENOVATED, ALL INCLUSIVE - 3 Bedroom/2 full bath completely furnished end unit offers exceptional privacy and

35 Photos

679 Johnston Park Avenue, Simcoe, ON , MLS #S13566270 , Image - 1

679 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13566270

Residential Condo & Other (Condo Apartment)

$4000.0

3 Beds
2 Baths
1000-1199 sq-ft

Seasonal winter rental in Lighthouse Point with flexible dates, minimum 4 month rental term. Bright & spacious updated 3 bedroom 2 bath has been fully

Houses for Rent in Collingwood ON Under $500K - P2