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Holiday Rentals in Collingwood

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125 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
Match: Sleeps
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308, Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
308, Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
308, Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

308, Studio - Downtown Collingwood, Luxury Boutique Hotel.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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FALL SPECIAL *Modern Condo*Mins from Lake, Beach, Trails, Spa, Blue M Village, holiday rental in Collingwood
FALL SPECIAL *Modern Condo*Mins from Lake, Beach, Trails, Spa, Blue M Village, holiday rental in Collingwood
FALL SPECIAL *Modern Condo*Mins from Lake, Beach, Trails, Spa, Blue M Village, holiday rental in Collingwood

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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102, Deluxe Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
102, Deluxe Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
102, Deluxe Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

102, Deluxe Studio - Downtown Collingwood, Luxury Boutique Hotel.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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206, Premium Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
206, Premium Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
206, Premium Studio - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

206, Premium Studio - Downtown Collingwood, Luxury Boutique Hotel.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Collingwood Contemporary Studio Apartment (97039), holiday rental in Collingwood
Downtown Collingwood Contemporary Studio Apartment (97039), holiday rental in Collingwood
Downtown Collingwood Contemporary Studio Apartment (97039), holiday rental in Collingwood

Downtown Collingwood Contemporary Studio Apartment (97039)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 9 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 9 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 9 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 9 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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205, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
205, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
205, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

205, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 10 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 10 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 10 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 10 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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103, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
103, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
103, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

103, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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
More info
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Room 11 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 11 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 11 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 11 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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 2
Match: Sleeps
More info
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1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water, holiday rental in Collingwood
1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water, holiday rental in Collingwood
1 Bedroom condo at Living Water Resort & Spa - 1 Bedroom condo at Living Water, holiday rental in Collingwood

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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204, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
204, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
204, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

204, 1 Bedroom - Downtown Collingwood, Luxury Boutique Hotel.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy Apartment in Thriving Downtown Collingwood (97038), holiday rental in Collingwood
Cozy Apartment in Thriving Downtown Collingwood (97038), holiday rental in Collingwood
Cozy Apartment in Thriving Downtown Collingwood (97038), holiday rental in Collingwood

Cozy Apartment in Thriving Downtown Collingwood (97038)

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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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
Match: Sleeps
More info
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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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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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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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
More info
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Room 7 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 7 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 7 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 7 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Beautifully renovated Suite in Collingwood!, holiday rental in Collingwood
Beautifully renovated Suite in Collingwood!, holiday rental in Collingwood
Beautifully renovated Suite in Collingwood!, holiday rental in Collingwood

Beautifully renovated Suite in Collingwood!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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
More info
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Room 1 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 1 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 1 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 1 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Room 6 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 6 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 6 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 6 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Luxury Contemporary Condo in Downtown Collingwood (97044), holiday rental in Collingwood
Luxury Contemporary Condo in Downtown Collingwood (97044), holiday rental in Collingwood
Luxury Contemporary Condo in Downtown Collingwood (97044), holiday rental in Collingwood

Luxury Contemporary Condo in Downtown Collingwood (97044)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful studio unit at resort, sleeps 2, holiday rental in Collingwood
Beautiful studio unit at resort, sleeps 2, holiday rental in Collingwood
Beautiful studio unit at resort, sleeps 2, holiday rental in Collingwood

Beautiful studio unit at resort, sleeps 2

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Stunning 2 bedroom home, heart of Downtown Collingwood, holiday rental in Collingwood
Stunning 2 bedroom home, heart of Downtown Collingwood, holiday rental in Collingwood
Stunning 2 bedroom home, heart of Downtown Collingwood, holiday rental in Collingwood

Stunning 2 bedroom home, heart of Downtown Collingwood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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B-1, 2 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
B-1, 2 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood
B-1, 2 Bedroom - Downtown Collingwood, Luxury Boutique Hotel., holiday rental in Collingwood

B-1, 2 Bedroom - Downtown Collingwood, Luxury Boutique Hotel.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Beautiful 3 Bdrm Upper Unit on 1.5 acres - Steps to Beach, holiday rental in Collingwood
Beautiful 3 Bdrm Upper Unit on 1.5 acres - Steps to Beach, holiday rental in Collingwood
Beautiful 3 Bdrm Upper Unit on 1.5 acres - Steps to Beach, holiday rental in Collingwood

Beautiful 3 Bdrm Upper Unit on 1.5 acres - Steps to Beach

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
More info
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Modern Condo in Cranberry Village *Exterior Access * Mins to Ski Hills Spa Lake, holiday rental in Collingwood
Modern Condo in Cranberry Village *Exterior Access * Mins to Ski Hills Spa Lake, holiday rental in Collingwood
Modern Condo in Cranberry Village *Exterior Access * Mins to Ski Hills Spa Lake, holiday rental in Collingwood

Modern Condo in Cranberry Village *Exterior Access * Mins to Ski Hills Spa Lake

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Bright and Spacious Condo in Downtown Collingwood (97043), holiday rental in Collingwood
Bright and Spacious Condo in Downtown Collingwood (97043), holiday rental in Collingwood
Bright and Spacious Condo in Downtown Collingwood (97043), holiday rental in Collingwood

Bright and Spacious Condo in Downtown Collingwood (97043)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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 2
Match: Sleeps
More info
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Beautiful, new, private apartment in Downtown Collingwood. Walk to all amenities, holiday rental in Collingwood
Beautiful, new, private apartment in Downtown Collingwood. Walk to all amenities, holiday rental in Collingwood
Beautiful, new, private apartment in Downtown Collingwood. Walk to all amenities, holiday rental in Collingwood

Beautiful, new, private apartment in Downtown Collingwood. Walk to all amenities

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Room 4 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 4 - 11 Rooms Boutique Hotel, holiday rental in Collingwood
Room 4 - 11 Rooms Boutique Hotel, holiday rental in Collingwood

Room 4 - 11 Rooms Boutique Hotel

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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4 month SKI SEASON $9800 no tax to pay All Inclusive” Or 1 month $2900, holiday rental in Collingwood
4 month SKI SEASON $9800 no tax to pay All Inclusive” Or 1 month $2900, holiday rental in Collingwood
4 month SKI SEASON $9800 no tax to pay All Inclusive” Or 1 month $2900, holiday rental in Collingwood

4 month SKI SEASON $9800 no tax to pay All Inclusive” Or 1 month $2900

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Recently renovated Regency in downtown Collingwood, holiday rental in Collingwood
Recently renovated Regency in downtown Collingwood, holiday rental in Collingwood
Recently renovated Regency in downtown Collingwood, holiday rental in Collingwood

Recently renovated Regency in downtown Collingwood

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Collingwood Downtown 2000ft2 with parking & private backyard, holiday rental in Collingwood
Collingwood Downtown 2000ft2 with parking & private backyard, holiday rental in Collingwood
Collingwood Downtown 2000ft2 with parking & private backyard, holiday rental in Collingwood

Collingwood Downtown 2000ft2 with parking & private backyard

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous Fully renovated 2 bedroom turn key suite, holiday rental in Collingwood
Gorgeous Fully renovated 2 bedroom turn key suite, holiday rental in Collingwood
Gorgeous Fully renovated 2 bedroom turn key suite, holiday rental in Collingwood

Gorgeous Fully renovated 2 bedroom turn key suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Stanley House - Upscale 2 Bedroom Gem - New Listing, holiday rental in Collingwood
Stanley House - Upscale 2 Bedroom Gem - New Listing, holiday rental in Collingwood
Stanley House - Upscale 2 Bedroom Gem - New Listing, holiday rental in Collingwood

Stanley House - Upscale 2 Bedroom Gem - New Listing

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful Waterfront Chalet, holiday rental in Collingwood
Beautiful Waterfront Chalet, holiday rental in Collingwood
Beautiful Waterfront Chalet, holiday rental in Collingwood

Beautiful Waterfront Chalet

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Ski Chalet by the Beach, holiday rental in Collingwood
Ski Chalet by the Beach, holiday rental in Collingwood
Ski Chalet by the Beach, holiday rental in Collingwood

Ski Chalet by the Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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19th century school house, modernized to a family home. Mins from Blue Mountain, holiday rental in Collingwood
19th century school house, modernized to a family home. Mins from Blue Mountain, holiday rental in Collingwood
19th century school house, modernized to a family home. Mins from Blue Mountain, holiday rental in Collingwood

19th century school house, modernized to a family home. Mins from Blue Mountain

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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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
More info
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Home Away From Home (83135), holiday rental in Collingwood
Home Away From Home (83135), holiday rental in Collingwood
Home Away From Home (83135), holiday rental in Collingwood

Home Away From Home (83135)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Secluded Simcoe St. Treasure (91600), holiday rental in Collingwood
Secluded Simcoe St. Treasure (91600), holiday rental in Collingwood
Secluded Simcoe St. Treasure (91600), holiday rental in Collingwood

Secluded Simcoe St. Treasure (91600)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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REDUCED!!!, holiday rental in Collingwood
REDUCED!!!, holiday rental in Collingwood
REDUCED!!!, holiday rental in Collingwood

REDUCED!!!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about Collingwood