Jayne's Cottages

Winter/Ski Season Features

Winter/Ski Season Features

Alternate pricing options are available for some properties. Keep an eye out for clickable prices to see the other options!

Wyndsong Farm

Location: Farmhouse in Creemore

From C$7,000 - C$8,050 /Week
  • C$28,000 /Month
  • C$7,000 /Summer Week
  • C$8,050 /Super Peak Week
( plus taxes and fees )

WYNDSONG FARM AREA Located within walking distance of the well-known hamlet of Creemore. Less than 2 hours from Toronto, 25 mins to downtown Collingwood and 30 mins to Blue Mountain. Perfectly situated to enjoy the many nearby ski and golf facilities including Devils Glen and Mansfield ski clubs (both 15 mins drive), as well as an abundance of outdoor activities and walking trails (both on and off the property!). Less…...

A tranquil farm experience with 150 acres of rolling hills and gorgeous views in every direction! Walk to the charming town of Creemore. The property boasts a 5bdrm farmhouse & separate 2 bdrm apartment, 3.5 baths, swimming pond, trails, etc!

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  • 5
  • 4

Wyndsong Farm

WYNDSONG FARM AREA Located within walking distance of the well-known hamlet of Creemore. Less than 2 hours from Toronto, 25 mins to downtown Collingwood and 30 mins to Blue Mountain. Perfectly situated to enjoy the many nearby ski and golf facilities including Devils Glen and Mansfield ski clubs (both 15 mins drive), as well as an abundance of outdoor activities and walking trails (both on and off the property!). Less…

Bedrooms 5
Bathrooms 4
# of Guests 12
Pet Friendly? Yes

Collingwoodlands Cabin

Location: Chalet in Collingwood

From C$7,000 - C$8,050 /Week
  • C$19,500 /Month
  • C$7,000 /Summer Week
  • C$8,050 /Super Peak Week
( plus taxes and fees )

COLLINGWOODLANDS CABIN AREA Location Location Location! Collingwoodlands Cabin is nestled in the heart of Ontario's four season playground - Collingwood! Only 2 minutes from Osler Bluff Ski Club and 5 minutes from the Blue Mountain Village! PROPERTY COLLINGWOODLANDS CABIN - Nestled on a luxurious cul-de-sac, this property looks every bit like the chalet you want to be renting for the ski season! The warm wood exterior and 5 dormers provide…...

Luxurious 5 bedroom Chalet + Bunkie in the heart of ski country! Only 2 minutes from Osler Bluff and 5 minutes from the Blue Mountain Village!

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  • 5
  • 4

Collingwoodlands Cabin

COLLINGWOODLANDS CABIN AREA Location Location Location! Collingwoodlands Cabin is nestled in the heart of Ontario's four season playground - Collingwood! Only 2 minutes from Osler Bluff Ski Club and 5 minutes from the Blue Mountain Village! PROPERTY COLLINGWOODLANDS CABIN - Nestled on a luxurious cul-de-sac, this property looks every bit like the chalet you want to be renting for the ski season! The warm wood exterior and 5 dormers provide…

Bedrooms 5
Bathrooms 4
# of Guests 14
Pet Friendly? Yes

Bluebird Bungalow

Location: Bungalow in Singhampton

From C$6,000 - C$6,900 /Week
  • C$15,000 /Month
  • C$6,000 /Summer Week
  • C$6,900 /Super Peak Week
( plus taxes and fees )

"BLUEBIRD BUNGLOW" AREA Situated just outside of Singhampton, the Bluebird Bungalow is 1 hour and 30 minutes from Toronto! It is in great proximity to all ski hills including; 15 minutes to Devil's Glen Country Club, 20 minutes to Beaver Valley Ski Club, 20 minutes to the Osler Bluff Ski Club and 30 mins to Blue Mountain Village! In the summer, enjoy golfing at any of the close Golf Courses…...

The beautiful Bluebird Bungalow is awaiting your arrival! Just 30 minutes south of Collingwood and 1.5 hours north of Toronto, it is in great proximity for skiers and outdoor enthusiasts alike! Features a brand new hot tub and mini garage gym!

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  • 5
  • 3

Bluebird Bungalow

"BLUEBIRD BUNGLOW" AREA Situated just outside of Singhampton, the Bluebird Bungalow is 1 hour and 30 minutes from Toronto! It is in great proximity to all ski hills including; 15 minutes to Devil's Glen Country Club, 20 minutes to Beaver Valley Ski Club, 20 minutes to the Osler Bluff Ski Club and 30 mins to Blue Mountain Village! In the summer, enjoy golfing at any of the close Golf Courses…

Bedrooms 5
Bathrooms 3
# of Guests 10
Pet Friendly? Yes

Blue Mountain Cottage

Location: House in Collingwood

From C$5,133 - C$5,903 /Week
  • C$14,500 /Month
  • C$5,133 /Summer Week
  • C$5,903 /Super Peak Week
( plus taxes and fees )

BLUE MOUNTAIN COTTAGE AREA Located only 800 metres from the Blue Mountain Village, in Ontario's four season playground, Blue Mountain Cottage offers proximity to a variety of activities to keep the entire family busy! Peruse the village shops, cafe's and enjoy meals at any of the gourmet restaurants. Nearby golf courses, hiking trails and beautiful Georgian Bay Beaches provide days of relaxation and fun for all! Those seeking a thrill…...

This cozy home is only 800 metres from Blue Mountain Village! Enjoy many outdoor activities including hiking the Bruce Trail, Zip Lines, Mountain biking at Blue, or swimming in nearby Georgian Bay!

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  • 5
  • 3

Blue Mountain Cottage

BLUE MOUNTAIN COTTAGE AREA Located only 800 metres from the Blue Mountain Village, in Ontario's four season playground, Blue Mountain Cottage offers proximity to a variety of activities to keep the entire family busy! Peruse the village shops, cafe's and enjoy meals at any of the gourmet restaurants. Nearby golf courses, hiking trails and beautiful Georgian Bay Beaches provide days of relaxation and fun for all! Those seeking a thrill…

Bedrooms 5
Bathrooms 3
# of Guests 8
Pet Friendly? Yes

Collingwinds

Location: Chalet in The Blue Mountains

From C$5,131 - C$5,901 /Week
  • C$22,000 /Month
  • C$5,131 /Summer Week
  • C$5,901 /Super Peak Week
( plus taxes and fees )

COLLINGWINDS AREA Located in the Windfall Development area at the bottom of Blue Mountain Resort, this unique Chalet offers 5 bedrooms including 2 Primary Suites which makes a perfect location for 2 families to share the beauty of the area all within a 10 minute walk to the village and some of Ontario's premier winter entertainment. COLLINGWINDS PROPERTY Surround yourself in this magnificent property that offers a backyard kidney shaped…...

Charming 5 bed 5 bath chalet including 2 primary suites - a 10 minute walk to the South Chair at Blue Mountain!

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  • 5
  • 5

Collingwinds

COLLINGWINDS AREA Located in the Windfall Development area at the bottom of Blue Mountain Resort, this unique Chalet offers 5 bedrooms including 2 Primary Suites which makes a perfect location for 2 families to share the beauty of the area all within a 10 minute walk to the village and some of Ontario's premier winter entertainment. COLLINGWINDS PROPERTY Surround yourself in this magnificent property that offers a backyard kidney shaped…

Bedrooms 5
Bathrooms 5
# of Guests 10
Pet Friendly? Yes

Century Chic

Location: House in Collingwood

From C$5,040 - C$5,796 /Week
  • C$14,000 /Month
  • C$5,040 /Summer Week
  • C$5,796 /Super Peak Week
( plus taxes and fees )

CENTURY CHIC AREA Welcome to the heart of Southern Georgian Bay! Enjoy four-seasons recreation in the centre of historic Collingwood. Boasting sophisticated charm on a pre-eminent “Tree Street”, this beautifully renovated and designer-decorated property is an ideal retreat for families or those seeking the active Collingwood lifestyle. The region's ski and golf clubs are minutes away, while the town’s best shops, restaurants, weekly Farmers Market, patios (no need for driving…...

Exquisite century home located in charming downtown Collingwood. You will never want to leave this professionally decorated house that features 4bedrooms, 3bathrooms, a spacious games room on the third level equipped with a projector screen!

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  • 4
  • 4

Century Chic

CENTURY CHIC AREA Welcome to the heart of Southern Georgian Bay! Enjoy four-seasons recreation in the centre of historic Collingwood. Boasting sophisticated charm on a pre-eminent “Tree Street”, this beautifully renovated and designer-decorated property is an ideal retreat for families or those seeking the active Collingwood lifestyle. The region's ski and golf clubs are minutes away, while the town’s best shops, restaurants, weekly Farmers Market, patios (no need for driving…

Bedrooms 4
Bathrooms 4
# of Guests 8
Pet Friendly? Yes

Chalet du Mt Tremblant

Location: Chalet in Mont-Tremblant

From C$4,375 /Week
  • C$19,995 /Month
( plus taxes and fees )

CHALET DU MT TREMBLANT AREA Location, location, location! Set in the spectacular Laurentian Mountains, Mont-Tremblant Ski Resort is a year round playground on the shores of Lake Tremblant. Live to Play is the motto here and activities abound in every season. In the winter enjoy skiing/snowboarding, cross-country skiing, ice climbing, ice fishing, fat biking, dog sledding, skating, snow shoeing, hiking, and snowmobiling. In other seasons hit the links at Le…...

This 4,500 sq ft premiere 6 bed, 5 bath chalet with hot tub, games and theatre rooms, is located right on the resort at Mont-Tremblant, a 2 minute free shuttle ride to ski lifts and the pedestrian village. Less than 2 hours from Montreal and Ottawa.

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  • 6
  • 5

Chalet du Mt Tremblant

CHALET DU MT TREMBLANT AREA Location, location, location! Set in the spectacular Laurentian Mountains, Mont-Tremblant Ski Resort is a year round playground on the shores of Lake Tremblant. Live to Play is the motto here and activities abound in every season. In the winter enjoy skiing/snowboarding, cross-country skiing, ice climbing, ice fishing, fat biking, dog sledding, skating, snow shoeing, hiking, and snowmobiling. In other seasons hit the links at Le…

Bedrooms 6
Bathrooms 5
# of Guests 12
Pet Friendly? No
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