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Holiday Homes in Collingwood

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111 rentals in Collingwood.
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Beautiful Log Cabin/chalet perfect for a romantic getaway, holiday rental in Collingwood
Beautiful Log Cabin/chalet perfect for a romantic getaway, holiday rental in Collingwood
Beautiful Log Cabin/chalet perfect for a romantic getaway, holiday rental in Collingwood

Beautiful Log Cabin/chalet perfect for a romantic getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Quiet Retreat - Perfect Couple’s Getaway!, holiday rental in Collingwood
Quiet Retreat - Perfect Couple’s Getaway!, holiday rental in Collingwood
Quiet Retreat - Perfect Couple’s Getaway!, holiday rental in Collingwood

Quiet Retreat - Perfect Couple’s Getaway!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Condo mins to *Lake*Beach*Village*Exterior Access*Free Provincial Parking, holiday rental in Collingwood
Modern Condo mins to *Lake*Beach*Village*Exterior Access*Free Provincial Parking, holiday rental in Collingwood
Modern Condo mins to *Lake*Beach*Village*Exterior Access*Free Provincial Parking, holiday rental in Collingwood

Modern Condo mins to *Lake*Beach*Village*Exterior Access*Free Provincial Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Home Away from Home in Collingwood 2 Bedroom Retreat - Minutes to Blue Mountain, holiday rental in Collingwood
Home Away from Home in Collingwood 2 Bedroom Retreat - Minutes to Blue Mountain, holiday rental in Collingwood
Home Away from Home in Collingwood 2 Bedroom Retreat - Minutes to Blue Mountain, holiday rental in Collingwood

Home Away from Home in Collingwood 2 Bedroom Retreat - Minutes to Blue Mountain

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Family Friendly Modern & Chic Condo - Your Sanctuary Suite. Welcome gift., holiday rental in Collingwood
Family Friendly Modern & Chic Condo - Your Sanctuary Suite. Welcome gift., holiday rental in Collingwood
Family Friendly Modern & Chic Condo - Your Sanctuary Suite. Welcome gift., holiday rental in Collingwood

Family Friendly Modern & Chic Condo - Your Sanctuary Suite. Welcome gift.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Blue Mountain/Collingwood Chalet Retreat, holiday rental in Collingwood
Blue Mountain/Collingwood Chalet Retreat, holiday rental in Collingwood
Blue Mountain/Collingwood Chalet Retreat, holiday rental in Collingwood

Blue Mountain/Collingwood Chalet Retreat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hillside Studio 1 in Blue Mountain, Mountain View, Full Kitchen, Free Parking, holiday rental in Collingwood
Hillside Studio 1 in Blue Mountain, Mountain View, Full Kitchen, Free Parking, holiday rental in Collingwood
Hillside Studio 1 in Blue Mountain, Mountain View, Full Kitchen, Free Parking, holiday rental in Collingwood

Hillside Studio 1 in Blue Mountain, Mountain View, Full Kitchen, Free Parking

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern Condo Steps From Historic Downtown Collingwood Charm, holiday rental in Collingwood
Modern Condo Steps From Historic Downtown Collingwood Charm, holiday rental in Collingwood
Modern Condo Steps From Historic Downtown Collingwood Charm, holiday rental in Collingwood

Modern Condo Steps From Historic Downtown Collingwood Charm

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PER MONTH? 4 MONTH SKI SEASONAL RENTAL? or ANNUALLY ?  furnished & all Inclusive, holiday rental in Collingwood
PER MONTH? 4 MONTH SKI SEASONAL RENTAL? or ANNUALLY ?  furnished & all Inclusive, holiday rental in Collingwood
PER MONTH? 4 MONTH SKI SEASONAL RENTAL? or ANNUALLY ?  furnished & all Inclusive, holiday rental in Collingwood

PER MONTH? 4 MONTH SKI SEASONAL RENTAL? or ANNUALLY ? furnished & all Inclusive

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Modern Condo *COLLINGWOOD *Mins from Lake, Beach, Trails, Spa, Blue M Village , holiday rental in Collingwood
Modern Condo *COLLINGWOOD *Mins from Lake, Beach, Trails, Spa, Blue M Village , holiday rental in Collingwood
Modern Condo *COLLINGWOOD *Mins from Lake, Beach, Trails, Spa, Blue M Village , holiday rental in Collingwood

Modern Condo *COLLINGWOOD *Mins from Lake, Beach, Trails, Spa, Blue M Village

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Lodge Suite Blue Mountain quiet escape, holiday rental in Collingwood
Lodge Suite Blue Mountain quiet escape, holiday rental in Collingwood
Lodge Suite Blue Mountain quiet escape, holiday rental in Collingwood

Lodge Suite Blue Mountain quiet escape

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Gorgeous modern brand new townhouse Sleeps 6-8

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Blue Mountain Slopes, Famous Wasaga Beach, Collingwood Exquisite Downtown are Ri, holiday rental in Collingwood
Blue Mountain Slopes, Famous Wasaga Beach, Collingwood Exquisite Downtown are Ri, holiday rental in Collingwood
Blue Mountain Slopes, Famous Wasaga Beach, Collingwood Exquisite Downtown are Ri, holiday rental in Collingwood

Blue Mountain Slopes, Famous Wasaga Beach, Collingwood Exquisite Downtown are Ri

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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★Core Downtown★Walk to Lake★Minutes from Mountain, holiday rental in Collingwood
★Core Downtown★Walk to Lake★Minutes from Mountain, holiday rental in Collingwood
★Core Downtown★Walk to Lake★Minutes from Mountain, holiday rental in Collingwood

★Core Downtown★Walk to Lake★Minutes from Mountain

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Century Farmhouse set on 2 acres, holiday rental in Collingwood
Century Farmhouse set on 2 acres, holiday rental in Collingwood
Century Farmhouse set on 2 acres, holiday rental in Collingwood

Century Farmhouse set on 2 acres

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski Paradise! Ground flr. Lighthouse Point. Avail March & April 2023., holiday rental in Collingwood
Ski Paradise! Ground flr. Lighthouse Point. Avail March & April 2023., holiday rental in Collingwood
Ski Paradise! Ground flr. Lighthouse Point. Avail March & April 2023., holiday rental in Collingwood

Ski Paradise! Ground flr. Lighthouse Point. Avail March & April 2023.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Seasonal Family Condo Rental near Blue Mountain, holiday rental in Collingwood
Seasonal Family Condo Rental near Blue Mountain, holiday rental in Collingwood
Seasonal Family Condo Rental near Blue Mountain, holiday rental in Collingwood

Seasonal Family Condo Rental near Blue Mountain

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Slope-Side Blue Mountain True Ski In/Ski Out, holiday rental in Collingwood
Slope-Side Blue Mountain True Ski In/Ski Out, holiday rental in Collingwood
Slope-Side Blue Mountain True Ski In/Ski Out, holiday rental in Collingwood

Slope-Side Blue Mountain True Ski In/Ski Out

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water R, holiday rental in Collingwood
1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water R, holiday rental in Collingwood
1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water R, holiday rental in Collingwood

1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water R

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious retreat in beautiful Blue Fairway—minutes from Blue Mountain slopes!, holiday rental in Collingwood
Spacious retreat in beautiful Blue Fairway—minutes from Blue Mountain slopes!, holiday rental in Collingwood
Spacious retreat in beautiful Blue Fairway—minutes from Blue Mountain slopes!, holiday rental in Collingwood

Spacious retreat in beautiful Blue Fairway—minutes from Blue Mountain slopes!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A Grand 3 Bed Room Detached Home in Collingwood for a Relaxed Stay., holiday rental in Collingwood
A Grand 3 Bed Room Detached Home in Collingwood for a Relaxed Stay., holiday rental in Collingwood
A Grand 3 Bed Room Detached Home in Collingwood for a Relaxed Stay., holiday rental in Collingwood

A Grand 3 Bed Room Detached Home in Collingwood for a Relaxed Stay.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Lighthouse Point Waterfront Condo, holiday rental in Collingwood
Spectacular Lighthouse Point Waterfront Condo, holiday rental in Collingwood
Spectacular Lighthouse Point Waterfront Condo, holiday rental in Collingwood

Spectacular Lighthouse Point Waterfront Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 1 Bedroom Condo that Sleeps 6, holiday rental in Collingwood
Spacious 1 Bedroom Condo that Sleeps 6, holiday rental in Collingwood
Spacious 1 Bedroom Condo that Sleeps 6, holiday rental in Collingwood

Spacious 1 Bedroom Condo that Sleeps 6

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Perfect Get Away Retreat Awaits You, holiday rental in Collingwood
Your Perfect Get Away Retreat Awaits You, holiday rental in Collingwood
Your Perfect Get Away Retreat Awaits You, holiday rental in Collingwood

Your Perfect Get Away Retreat Awaits You

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Winter Rental Lighthouse Point, Collingwood, ON, holiday rental in Collingwood
Winter Rental Lighthouse Point, Collingwood, ON, holiday rental in Collingwood
Winter Rental Lighthouse Point, Collingwood, ON, holiday rental in Collingwood

Winter Rental Lighthouse Point, Collingwood, ON

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A Thyme to Rest, holiday rental in Collingwood
A Thyme to Rest, holiday rental in Collingwood
A Thyme to Rest, holiday rental in Collingwood

A Thyme to Rest

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pet friendly ground level one-bedroom on pond and mountainside, holiday rental in Collingwood
Pet friendly ground level one-bedroom on pond and mountainside, holiday rental in Collingwood
Pet friendly ground level one-bedroom on pond and mountainside, holiday rental in Collingwood

Pet friendly ground level one-bedroom on pond and mountainside

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3 BEDROOM WATERFRONT BLUE MOUNTAIN VACATION LOFT, holiday rental in Collingwood
3 BEDROOM WATERFRONT BLUE MOUNTAIN VACATION LOFT, holiday rental in Collingwood
3 BEDROOM WATERFRONT BLUE MOUNTAIN VACATION LOFT, holiday rental in Collingwood

3 BEDROOM WATERFRONT BLUE MOUNTAIN VACATION LOFT

Condo/Apartment
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Two-Bedroom Suite, holiday rental in Collingwood
Two-Bedroom Suite, holiday rental in Collingwood
Two-Bedroom Suite, holiday rental in Collingwood

Two-Bedroom Suite

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Collingwood Resort Sleeps 4-Elvis Presley Festival, holiday rental in Collingwood
Collingwood Resort Sleeps 4-Elvis Presley Festival, holiday rental in Collingwood
Collingwood Resort Sleeps 4-Elvis Presley Festival, holiday rental in Collingwood

Collingwood Resort Sleeps 4-Elvis Presley Festival

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury at Blue Mountain Collingwood, holiday rental in Collingwood
Luxury at Blue Mountain Collingwood, holiday rental in Collingwood
Luxury at Blue Mountain Collingwood, holiday rental in Collingwood

Luxury at Blue Mountain Collingwood

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Mountain 6 Bdrm VERY PRIVATE Cottage on 10 acres, Outdoor Hot Tub, holiday rental in Collingwood
Blue Mountain 6 Bdrm VERY PRIVATE Cottage on 10 acres, Outdoor Hot Tub, holiday rental in Collingwood
Blue Mountain 6 Bdrm VERY PRIVATE Cottage on 10 acres, Outdoor Hot Tub, holiday rental in Collingwood

Blue Mountain 6 Bdrm VERY PRIVATE Cottage on 10 acres, Outdoor Hot Tub

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Centrally Located Chic Collingwood Condo, holiday rental in Collingwood
Centrally Located Chic Collingwood Condo, holiday rental in Collingwood
Centrally Located Chic Collingwood Condo, holiday rental in Collingwood

Centrally Located Chic Collingwood Condo

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Elegant & Updated Century Red Brick in Downtown Collingwood, holiday rental in Collingwood
Elegant & Updated Century Red Brick in Downtown Collingwood, holiday rental in Collingwood
Elegant & Updated Century Red Brick in Downtown Collingwood, holiday rental in Collingwood

Elegant & Updated Century Red Brick in Downtown Collingwood

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Stunning Chalet in the heart of Collingwood! 6 Bed, 5 Bath! 2-Acre Property!, holiday rental in Collingwood
Stunning Chalet in the heart of Collingwood! 6 Bed, 5 Bath! 2-Acre Property!, holiday rental in Collingwood
Stunning Chalet in the heart of Collingwood! 6 Bed, 5 Bath! 2-Acre Property!, holiday rental in Collingwood

Stunning Chalet in the heart of Collingwood! 6 Bed, 5 Bath! 2-Acre Property!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood

Beautiful 2 bedroom unit at resort, sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood

Beautiful 2 bedroom unit at resort, sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood

Beautiful 2 bedroom unit at resort, sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy, refreshing, 6 minutes to Blue Mountain Resort Village, holiday rental in Collingwood
Cozy, refreshing, 6 minutes to Blue Mountain Resort Village, holiday rental in Collingwood
Cozy, refreshing, 6 minutes to Blue Mountain Resort Village, holiday rental in Collingwood

Cozy, refreshing, 6 minutes to Blue Mountain Resort Village

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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A gorgeous Coach House located in the heart of Collingwood, holiday rental in Collingwood
A gorgeous Coach House located in the heart of Collingwood, holiday rental in Collingwood
A gorgeous Coach House located in the heart of Collingwood, holiday rental in Collingwood

A gorgeous Coach House located in the heart of Collingwood

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Paridise Point Ski Rental, holiday rental in Collingwood
Paridise Point Ski Rental, holiday rental in Collingwood
Paridise Point Ski Rental, holiday rental in Collingwood

Paridise Point Ski Rental

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Downtown 4 bedroom house, holiday rental in Collingwood
Downtown 4 bedroom house, holiday rental in Collingwood
Downtown 4 bedroom house, holiday rental in Collingwood

Downtown 4 bedroom house

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bright rennovated 5 Bedroom Townhouse Baking onto Golf Course, holiday rental in Collingwood
Bright rennovated 5 Bedroom Townhouse Baking onto Golf Course, holiday rental in Collingwood
Bright rennovated 5 Bedroom Townhouse Baking onto Golf Course, holiday rental in Collingwood

Bright rennovated 5 Bedroom Townhouse Baking onto Golf Course

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 2 bedroom unit at resort, sleeps 6, holiday rental in Collingwood

Beautiful 2 bedroom unit at resort, sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lux Chalet - high speed internet in highly desired Briarwood - Collingwood, holiday rental in Collingwood
Lux Chalet - high speed internet in highly desired Briarwood - Collingwood, holiday rental in Collingwood
Lux Chalet - high speed internet in highly desired Briarwood - Collingwood, holiday rental in Collingwood

Lux Chalet - high speed internet in highly desired Briarwood - Collingwood

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lighthouse Point, Collingwood.  10 min to ski. 2 min to lake!  Main flr walkout., holiday rental in Collingwood
Lighthouse Point, Collingwood.  10 min to ski. 2 min to lake!  Main flr walkout., holiday rental in Collingwood
Lighthouse Point, Collingwood.  10 min to ski. 2 min to lake!  Main flr walkout., holiday rental in Collingwood

Lighthouse Point, Collingwood. 10 min to ski. 2 min to lake! Main flr walkout.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning, executive 2 bedrooms (2 bath) townhouse, holiday rental in Collingwood
Stunning, executive 2 bedrooms (2 bath) townhouse, holiday rental in Collingwood
Stunning, executive 2 bedrooms (2 bath) townhouse, holiday rental in Collingwood

Stunning, executive 2 bedrooms (2 bath) townhouse

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Awesome Studio Townhouse in Cranberry Village Collingwood!, holiday rental in Collingwood
Awesome Studio Townhouse in Cranberry Village Collingwood!, holiday rental in Collingwood
Awesome Studio Townhouse in Cranberry Village Collingwood!, holiday rental in Collingwood

Awesome Studio Townhouse in Cranberry Village Collingwood!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 1 bedroom unit at resort, sleeps 4, holiday rental in Collingwood
Beautiful 1 bedroom unit at resort, sleeps 4, holiday rental in Collingwood
Beautiful 1 bedroom unit at resort, sleeps 4, holiday rental in Collingwood

Beautiful 1 bedroom unit at resort, sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful 1 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 1 bedroom unit at resort, sleeps 6, holiday rental in Collingwood
Beautiful 1 bedroom unit at resort, sleeps 6, holiday rental in Collingwood

Beautiful 1 bedroom unit at resort, sleeps 6

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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