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Cookstown Family & Kid Friendly Rentals

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41 rentals in Cookstown.
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**Water Front** Duck Lake Guest House, vacation rental in Cookstown
**Water Front** Duck Lake Guest House, vacation rental in Cookstown
**Water Front** Duck Lake Guest House, vacation rental in Cookstown

**Water Front** Duck Lake Guest House

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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Country Cabin for Stays - WE ACCEPT BOOKINGS - Near Newmarket Toronto, vacation rental in Cookstown
Country Cabin for Stays - WE ACCEPT BOOKINGS - Near Newmarket Toronto, vacation rental in Cookstown
Country Cabin for Stays - WE ACCEPT BOOKINGS - Near Newmarket Toronto, vacation rental in Cookstown

Country Cabin for Stays - WE ACCEPT BOOKINGS - Near Newmarket Toronto

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - near Toronto Newmarket, vacation rental in Cookstown
Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - near Toronto Newmarket, vacation rental in Cookstown
Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - near Toronto Newmarket, vacation rental in Cookstown

Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - near Toronto Newmarket

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Unique Country Barn Studio, vacation rental in Cookstown
Unique Country Barn Studio, vacation rental in Cookstown
Unique Country Barn Studio, vacation rental in Cookstown

Unique Country Barn Studio

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Waterfront cottage on Lake Simcoe/Innisfil, vacation rental in Cookstown
Waterfront cottage on Lake Simcoe/Innisfil, vacation rental in Cookstown
Waterfront cottage on Lake Simcoe/Innisfil, vacation rental in Cookstown

Waterfront cottage on Lake Simcoe/Innisfil

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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Stylish, Modern 2nd Floor Private Apt. In Quiet Area, Close To Lake Simcoe, vacation rental in Cookstown
Stylish, Modern 2nd Floor Private Apt. In Quiet Area, Close To Lake Simcoe, vacation rental in Cookstown
Stylish, Modern 2nd Floor Private Apt. In Quiet Area, Close To Lake Simcoe, vacation rental in Cookstown

Stylish, Modern 2nd Floor Private Apt. In Quiet Area, Close To Lake Simcoe

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Waterfront Cottage On Lake Simcoe, vacation rental in Cookstown
Waterfront Cottage On Lake Simcoe, vacation rental in Cookstown
Waterfront Cottage On Lake Simcoe, vacation rental in Cookstown

Waterfront Cottage On Lake Simcoe

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - Near Toronto Newmarket, vacation rental in Cookstown
Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - Near Toronto Newmarket, vacation rental in Cookstown
Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - Near Toronto Newmarket, vacation rental in Cookstown

Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - Near Toronto Newmarket

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Executive Villa - Year Round Swim Spa & Game Room, vacation rental in Cookstown
Executive Villa - Year Round Swim Spa & Game Room, vacation rental in Cookstown
Executive Villa - Year Round Swim Spa & Game Room, vacation rental in Cookstown

Executive Villa - Year Round Swim Spa & Game Room

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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2 beds 2 baths bungalow near school, grocery and highway 400, vacation rental in Cookstown
2 beds 2 baths bungalow near school, grocery and highway 400, vacation rental in Cookstown
2 beds 2 baths bungalow near school, grocery and highway 400, vacation rental in Cookstown

2 beds 2 baths bungalow near school, grocery and highway 400

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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Adorable and spacious 3 bedrooms house close to all amenities/quite neighborhood, vacation rental in Cookstown
Adorable and spacious 3 bedrooms house close to all amenities/quite neighborhood, vacation rental in Cookstown
Adorable and spacious 3 bedrooms house close to all amenities/quite neighborhood, vacation rental in Cookstown

Adorable and spacious 3 bedrooms house close to all amenities/quite neighborhood

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Kid friendly
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Affordable and Spacious 2 bedroom house in a quite neighborhood and all amenties, vacation rental in Cookstown
Affordable and Spacious 2 bedroom house in a quite neighborhood and all amenties, vacation rental in Cookstown
Affordable and Spacious 2 bedroom house in a quite neighborhood and all amenties, vacation rental in Cookstown

Affordable and Spacious 2 bedroom house in a quite neighborhood and all amenties

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Chalet Ewart by the lake, vacation rental in Cookstown
Chalet Ewart by the lake, vacation rental in Cookstown
Chalet Ewart by the lake, vacation rental in Cookstown

Chalet Ewart by the lake

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
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Cozy & Private 1-BR Basement Suite w/Free Parking, vacation rental in Cookstown
Cozy & Private 1-BR Basement Suite w/Free Parking, vacation rental in Cookstown
Cozy & Private 1-BR Basement Suite w/Free Parking, vacation rental in Cookstown

Cozy & Private 1-BR Basement Suite w/Free Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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3 Bedroom Bungalow With Farm & Pond Near Innisfil Beach, vacation rental in Cookstown
3 Bedroom Bungalow With Farm & Pond Near Innisfil Beach, vacation rental in Cookstown
3 Bedroom Bungalow With Farm & Pond Near Innisfil Beach, vacation rental in Cookstown

3 Bedroom Bungalow With Farm & Pond Near Innisfil Beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Kid friendly
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Unique Country Barn Studio, vacation rental in Cookstown
Unique Country Barn Studio, vacation rental in Cookstown
Unique Country Barn Studio, vacation rental in Cookstown

Unique Country Barn Studio

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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1BDR Apartment in Cottage with 13-Acre Farm & Pond, vacation rental in Cookstown
1BDR Apartment in Cottage with 13-Acre Farm & Pond, vacation rental in Cookstown
1BDR Apartment in Cottage with 13-Acre Farm & Pond, vacation rental in Cookstown

1BDR Apartment in Cottage with 13-Acre Farm & Pond

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Cozy Lakehouse, vacation rental in Cookstown
Cozy Lakehouse, vacation rental in Cookstown
Cozy Lakehouse, vacation rental in Cookstown

Cozy Lakehouse

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Private and spacious 1 bedroom suite with hot tub, vacation rental in Cookstown
Private and spacious 1 bedroom suite with hot tub, vacation rental in Cookstown
Private and spacious 1 bedroom suite with hot tub, vacation rental in Cookstown

Private and spacious 1 bedroom suite with hot tub

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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City living in Cottage Country with all season activities, vacation rental in Cookstown
City living in Cottage Country with all season activities, vacation rental in Cookstown
City living in Cottage Country with all season activities, vacation rental in Cookstown

City living in Cottage Country with all season activities

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, Kid friendly
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Cozy Cottage Close to Lake Simcoe, vacation rental in Cookstown
Cozy Cottage Close to Lake Simcoe, vacation rental in Cookstown
Cozy Cottage Close to Lake Simcoe, vacation rental in Cookstown

Cozy Cottage Close to Lake Simcoe

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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CASA THE BEAR, Modern 2 Bedroom Condo South Barrie, vacation rental in Cookstown
CASA THE BEAR, Modern 2 Bedroom Condo South Barrie, vacation rental in Cookstown
CASA THE BEAR, Modern 2 Bedroom Condo South Barrie, vacation rental in Cookstown

CASA THE BEAR, Modern 2 Bedroom Condo South Barrie

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Brand new lavish home nearby Innisfil's Friday Harbour & Beach Park, vacation rental in Cookstown
Brand new lavish home nearby Innisfil's Friday Harbour & Beach Park, vacation rental in Cookstown
Brand new lavish home nearby Innisfil's Friday Harbour & Beach Park, vacation rental in Cookstown

Brand new lavish home nearby Innisfil's Friday Harbour & Beach Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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*Luxury* 4 Bdrm Home w/5 Bath & Fast Internet, vacation rental in Cookstown
*Luxury* 4 Bdrm Home w/5 Bath & Fast Internet, vacation rental in Cookstown
*Luxury* 4 Bdrm Home w/5 Bath & Fast Internet, vacation rental in Cookstown

*Luxury* 4 Bdrm Home w/5 Bath & Fast Internet

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Private lakefront gateway on Lake Simcoe, vacation rental in Cookstown
Private lakefront gateway on Lake Simcoe, vacation rental in Cookstown
Private lakefront gateway on Lake Simcoe, vacation rental in Cookstown

Private lakefront gateway on Lake Simcoe

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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House w/Barn from 1867, vacation rental in Cookstown
House w/Barn from 1867, vacation rental in Cookstown
House w/Barn from 1867, vacation rental in Cookstown

House w/Barn from 1867

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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The Mansion, Wasaga beach, Blue mountain, vacation rental in Cookstown
The Mansion, Wasaga beach, Blue mountain, vacation rental in Cookstown
The Mansion, Wasaga beach, Blue mountain, vacation rental in Cookstown

The Mansion, Wasaga beach, Blue mountain

Rental Home
6 bedrooms
6 bathrooms
Sleeps 25
Match: Sleeps, Kid friendly
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10 Acre Private Cottage + Hot-tub + Firepit, vacation rental in Cookstown
10 Acre Private Cottage + Hot-tub + Firepit, vacation rental in Cookstown
10 Acre Private Cottage + Hot-tub + Firepit, vacation rental in Cookstown

10 Acre Private Cottage + Hot-tub + Firepit

Rental Home
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps, Kid friendly
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Vacation Property, Cooks Bay,  Lake Simcoe., vacation rental in Cookstown
Vacation Property, Cooks Bay,  Lake Simcoe., vacation rental in Cookstown
Vacation Property, Cooks Bay,  Lake Simcoe., vacation rental in Cookstown

Vacation Property, Cooks Bay, Lake Simcoe.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Lake Simcoe Cottage. Winter Fishing Paradise, vacation rental in Cookstown
Lake Simcoe Cottage. Winter Fishing Paradise, vacation rental in Cookstown
Lake Simcoe Cottage. Winter Fishing Paradise, vacation rental in Cookstown

Lake Simcoe Cottage. Winter Fishing Paradise

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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Outdoor Life at Lake Simcoe, vacation rental in Cookstown
Outdoor Life at Lake Simcoe, vacation rental in Cookstown
Outdoor Life at Lake Simcoe, vacation rental in Cookstown

Outdoor Life at Lake Simcoe

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake., vacation rental in Cookstown
Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake., vacation rental in Cookstown
Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake., vacation rental in Cookstown

Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Cottage/Lake Simcoe/Innisfil/5 Bedrooms/10 Guests, vacation rental in Cookstown
Cottage/Lake Simcoe/Innisfil/5 Bedrooms/10 Guests, vacation rental in Cookstown
Cottage/Lake Simcoe/Innisfil/5 Bedrooms/10 Guests, vacation rental in Cookstown

Cottage/Lake Simcoe/Innisfil/5 Bedrooms/10 Guests

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Cody and warm house for family gathering and friends,12 mins away from beaches a, vacation rental in Cookstown
Cody and warm house for family gathering and friends,12 mins away from beaches a, vacation rental in Cookstown
Cody and warm house for family gathering and friends,12 mins away from beaches a, vacation rental in Cookstown

Cody and warm house for family gathering and friends,12 mins away from beaches a

Rental Home
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Lakefront Cottage with Amazing Views, Fishing, Activities Ideal for Families, vacation rental in Cookstown
Lakefront Cottage with Amazing Views, Fishing, Activities Ideal for Families, vacation rental in Cookstown
Lakefront Cottage with Amazing Views, Fishing, Activities Ideal for Families, vacation rental in Cookstown

Lakefront Cottage with Amazing Views, Fishing, Activities Ideal for Families

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Beautiful Lake Simcoe Cottage

Rental Home
6 bedrooms
1 bathroom
Sleeps 14
Match: Sleeps, Kid friendly
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Perfectly private⭐Perfectly Private & Cozy⭐ Kitchen☆Patio☆Netflx☆, vacation rental in Cookstown
Perfectly private⭐Perfectly Private & Cozy⭐ Kitchen☆Patio☆Netflx☆, vacation rental in Cookstown
Perfectly private⭐Perfectly Private & Cozy⭐ Kitchen☆Patio☆Netflx☆, vacation rental in Cookstown

Perfectly private⭐Perfectly Private & Cozy⭐ Kitchen☆Patio☆Netflx☆

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Home away from home, vacation rental in Cookstown
Home away from home, vacation rental in Cookstown
Home away from home, vacation rental in Cookstown

Home away from home

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps, Kid friendly
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House located on beautiful horse farm, vacation rental in Cookstown
House located on beautiful horse farm, vacation rental in Cookstown
House located on beautiful horse farm, vacation rental in Cookstown

House located on beautiful horse farm

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Spacious House near Lake Simcoe, vacation rental in Cookstown
Spacious House near Lake Simcoe, vacation rental in Cookstown
Spacious House near Lake Simcoe, vacation rental in Cookstown

Spacious House near Lake Simcoe

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Kid friendly
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Luxurious and spacious waterfront townhouse, vacation rental in Cookstown
Luxurious and spacious waterfront townhouse, vacation rental in Cookstown
Luxurious and spacious waterfront townhouse, vacation rental in Cookstown

Luxurious and spacious waterfront townhouse

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps, Kid friendly
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Alfa getaway (  Best View ), vacation rental in Cookstown
Alfa getaway (  Best View ), vacation rental in Cookstown
Alfa getaway (  Best View ), vacation rental in Cookstown

Alfa getaway ( Best View )

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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SHABBY SHACK ( glamping), vacation rental in Cookstown
SHABBY SHACK ( glamping), vacation rental in Cookstown
SHABBY SHACK ( glamping), vacation rental in Cookstown

SHABBY SHACK ( glamping)

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, vacation rental in Cookstown
Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, vacation rental in Cookstown
Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, vacation rental in Cookstown

Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Harbour Haven! Waterfront escape at Friday Harbour resort, vacation rental in Cookstown
Harbour Haven! Waterfront escape at Friday Harbour resort, vacation rental in Cookstown
Harbour Haven! Waterfront escape at Friday Harbour resort, vacation rental in Cookstown

Harbour Haven! Waterfront escape at Friday Harbour resort

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bright and charming rooms in a family house in Innisfil, vacation rental in Cookstown
Bright and charming rooms in a family house in Innisfil, vacation rental in Cookstown
Bright and charming rooms in a family house in Innisfil, vacation rental in Cookstown

Bright and charming rooms in a family house in Innisfil

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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1 Bedroom 1 Bathroom, vacation rental in Cookstown
1 Bedroom 1 Bathroom, vacation rental in Cookstown
1 Bedroom 1 Bathroom, vacation rental in Cookstown

1 Bedroom 1 Bathroom

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, vacation rental in Cookstown
PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, vacation rental in Cookstown
PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, vacation rental in Cookstown

PREMIUM LIVING PLACE / 2 BEDROOMS SUIT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy 1 bedroom 1 Bath in Beach Town, vacation rental in Cookstown
Cozy 1 bedroom 1 Bath in Beach Town, vacation rental in Cookstown
Cozy 1 bedroom 1 Bath in Beach Town, vacation rental in Cookstown

Cozy 1 bedroom 1 Bath in Beach Town

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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- Home away from home a place you don't want to leave  - Unit# 2, vacation rental in Cookstown
- Home away from home a place you don't want to leave  - Unit# 2, vacation rental in Cookstown
- Home away from home a place you don't want to leave  - Unit# 2, vacation rental in Cookstown

- Home away from home a place you don't want to leave - Unit# 2

Rental Home
1 bedroom
1 bathroom
Sleeps 1
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