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Cookstown Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
45 rentals in Cookstown.
John Wayne Cedar Oasis, holiday rental in Cookstown
John Wayne Cedar Oasis, holiday rental in Cookstown
John Wayne Cedar Oasis, holiday rental in Cookstown

John Wayne Cedar Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Cookstown match all your filters:
La Datcha Cottage Hot Tub, Sauna & Pool 
20 Wooded Acres of Grassland, holiday rental in Cookstown
La Datcha Cottage Hot Tub, Sauna & Pool 
20 Wooded Acres of Grassland, holiday rental in Cookstown
La Datcha Cottage Hot Tub, Sauna & Pool 
20 Wooded Acres of Grassland, holiday rental in Cookstown

La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Executive Villa - Year Round Swim Spa & Game Room, holiday rental in Cookstown
Executive Villa - Year Round Swim Spa & Game Room, holiday rental in Cookstown
Executive Villa - Year Round Swim Spa & Game Room, holiday rental in Cookstown

Executive Villa - Year Round Swim Spa & Game Room

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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✦9 Bedrooms ✦8,400 sqft Farm House ✦28 Acres ✦1 Hr from Toronto, holiday rental in Cookstown
✦9 Bedrooms ✦8,400 sqft Farm House ✦28 Acres ✦1 Hr from Toronto, holiday rental in Cookstown
✦9 Bedrooms ✦8,400 sqft Farm House ✦28 Acres ✦1 Hr from Toronto, holiday rental in Cookstown

✦9 Bedrooms ✦8,400 sqft Farm House ✦28 Acres ✦1 Hr from Toronto

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 22
Match: Sleeps
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3Bedroom 3bath &Office, kids party, playground, onsite storage/opt, pet, holiday rental in Cookstown
3Bedroom 3bath &Office, kids party, playground, onsite storage/opt, pet, holiday rental in Cookstown
3Bedroom 3bath &Office, kids party, playground, onsite storage/opt, pet, holiday rental in Cookstown

3Bedroom 3bath &Office, kids party, playground, onsite storage/opt, pet

Holiday Rental House
8 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Live large in a cozy space, holiday rental in Cookstown
Live large in a cozy space, holiday rental in Cookstown
Live large in a cozy space, holiday rental in Cookstown

Live large in a cozy space

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Private Suite in Bradford, holiday rental in Cookstown
Quiet Private Suite in Bradford, holiday rental in Cookstown
Quiet Private Suite in Bradford, holiday rental in Cookstown

Quiet Private Suite in Bradford

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stylish and Cozy Suite, holiday rental in Cookstown
Stylish and Cozy Suite, holiday rental in Cookstown
Stylish and Cozy Suite, holiday rental in Cookstown

Stylish and Cozy Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peaceful - 4 bdrm home with fast WIFI free parking, holiday rental in Cookstown
Peaceful - 4 bdrm home with fast WIFI free parking, holiday rental in Cookstown
Peaceful - 4 bdrm home with fast WIFI free parking, holiday rental in Cookstown

Peaceful - 4 bdrm home with fast WIFI free parking

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Master Bedroom Suite, holiday rental in Cookstown
Elegant Master Bedroom Suite, holiday rental in Cookstown
Elegant Master Bedroom Suite, holiday rental in Cookstown

Elegant Master Bedroom Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Experience Luxury Living-Minutes from Canada's Wonderland, holiday rental in Cookstown
Experience Luxury Living-Minutes from Canada's Wonderland, holiday rental in Cookstown
Experience Luxury Living-Minutes from Canada's Wonderland, holiday rental in Cookstown

Experience Luxury Living-Minutes from Canada's Wonderland

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Retreat with Outdoor Jacuzzi, holiday rental in Cookstown
Luxury Retreat with Outdoor Jacuzzi, holiday rental in Cookstown
Luxury Retreat with Outdoor Jacuzzi, holiday rental in Cookstown

Luxury Retreat with Outdoor Jacuzzi

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Guest House Bradford, holiday rental in Cookstown
Luxury Guest House Bradford, holiday rental in Cookstown
Luxury Guest House Bradford, holiday rental in Cookstown

Luxury Guest House Bradford

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Waterfront Lakehouse on Lake Simcoe. Great For Family Stays!, holiday rental in Cookstown
Stunning Waterfront Lakehouse on Lake Simcoe. Great For Family Stays!, holiday rental in Cookstown
Stunning Waterfront Lakehouse on Lake Simcoe. Great For Family Stays!, holiday rental in Cookstown

Stunning Waterfront Lakehouse on Lake Simcoe. Great For Family Stays!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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THE WHITE HOUSE ON THE HILL - Beautiful Country Home, holiday rental in Cookstown
THE WHITE HOUSE ON THE HILL - Beautiful Country Home, holiday rental in Cookstown
THE WHITE HOUSE ON THE HILL - Beautiful Country Home, holiday rental in Cookstown

THE WHITE HOUSE ON THE HILL - Beautiful Country Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking, holiday rental in Cookstown
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking, holiday rental in Cookstown
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking, holiday rental in Cookstown

House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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4 Bedrooms beautiful, elegant house, holiday rental in Cookstown
4 Bedrooms beautiful, elegant house, holiday rental in Cookstown
4 Bedrooms beautiful, elegant house, holiday rental in Cookstown

4 Bedrooms beautiful, elegant house

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful country escape 5 min. from beach, holiday rental in Cookstown
Beautiful country escape 5 min. from beach, holiday rental in Cookstown
Beautiful country escape 5 min. from beach, holiday rental in Cookstown

Beautiful country escape 5 min. from beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Blue House - 4 Bedrooms + Pool - Perfect for the Whole Family!, holiday rental in Cookstown
The Blue House - 4 Bedrooms + Pool - Perfect for the Whole Family!, holiday rental in Cookstown
The Blue House - 4 Bedrooms + Pool - Perfect for the Whole Family!, holiday rental in Cookstown

The Blue House - 4 Bedrooms + Pool - Perfect for the Whole Family!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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2 Bedroom Basement With Separate Entrance Family-friendly, holiday rental in Cookstown
2 Bedroom Basement With Separate Entrance Family-friendly, holiday rental in Cookstown
2 Bedroom Basement With Separate Entrance Family-friendly, holiday rental in Cookstown

2 Bedroom Basement With Separate Entrance Family-friendly

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Waterfront Lakehouse Innisfil Cooks Bay 45 min from GTA !, holiday rental in Cookstown
Charming Waterfront Lakehouse Innisfil Cooks Bay 45 min from GTA !, holiday rental in Cookstown
Charming Waterfront Lakehouse Innisfil Cooks Bay 45 min from GTA !, holiday rental in Cookstown

Charming Waterfront Lakehouse Innisfil Cooks Bay 45 min from GTA !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Simcoe County Cottage ★ Woodland Private Retreat ★ Hot Tub ★ Riverfront, holiday rental in Cookstown
Simcoe County Cottage ★ Woodland Private Retreat ★ Hot Tub ★ Riverfront, holiday rental in Cookstown
Simcoe County Cottage ★ Woodland Private Retreat ★ Hot Tub ★ Riverfront, holiday rental in Cookstown

Simcoe County Cottage ★ Woodland Private Retreat ★ Hot Tub ★ Riverfront

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, holiday rental in Cookstown
PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, holiday rental in Cookstown
PREMIUM LIVING PLACE / 2 BEDROOMS SUIT, holiday rental in Cookstown

PREMIUM LIVING PLACE / 2 BEDROOMS SUIT

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Mansion, Wasaga beach, Blue mountain, holiday rental in Cookstown
The Mansion, Wasaga beach, Blue mountain, holiday rental in Cookstown
The Mansion, Wasaga beach, Blue mountain, holiday rental in Cookstown

The Mansion, Wasaga beach, Blue mountain

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 25
Match: Sleeps
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Sunrise Villa on the Lake, holiday rental in Cookstown
Sunrise Villa on the Lake, holiday rental in Cookstown
Sunrise Villa on the Lake, holiday rental in Cookstown

Sunrise Villa on the Lake

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Brand new cozy 2 Bdrms Suite, holiday rental in Cookstown
Brand new cozy 2 Bdrms Suite, holiday rental in Cookstown
Brand new cozy 2 Bdrms Suite, holiday rental in Cookstown

Brand new cozy 2 Bdrms Suite

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Luxury|Games room, Steam rooms,Lake toys, holiday rental in Cookstown
Lakefront Luxury|Games room, Steam rooms,Lake toys, holiday rental in Cookstown
Lakefront Luxury|Games room, Steam rooms,Lake toys, holiday rental in Cookstown

Lakefront Luxury|Games room, Steam rooms,Lake toys

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lovely basement apartment in the heart of Bradford, holiday rental in Cookstown
Lovely basement apartment in the heart of Bradford, holiday rental in Cookstown
Lovely basement apartment in the heart of Bradford, holiday rental in Cookstown

Lovely basement apartment in the heart of Bradford

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Welcome to Lake House by Lis, where stunning lake views and serene sunsets await, holiday rental in Cookstown
Welcome to Lake House by Lis, where stunning lake views and serene sunsets await, holiday rental in Cookstown
Welcome to Lake House by Lis, where stunning lake views and serene sunsets await, holiday rental in Cookstown

Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sweet Deal! Spacious 4bd Home Comfortably Sleeps 10., holiday rental in Cookstown
Sweet Deal! Spacious 4bd Home Comfortably Sleeps 10., holiday rental in Cookstown
Sweet Deal! Spacious 4bd Home Comfortably Sleeps 10., holiday rental in Cookstown

Sweet Deal! Spacious 4bd Home Comfortably Sleeps 10.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Bradford Home - 4 Bedroom House, holiday rental in Cookstown
Luxury Bradford Home - 4 Bedroom House, holiday rental in Cookstown
Luxury Bradford Home - 4 Bedroom House, holiday rental in Cookstown

Luxury Bradford Home - 4 Bedroom House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy & Clean upper unit, holiday rental in Cookstown
Cozy & Clean upper unit, holiday rental in Cookstown
Cozy & Clean upper unit, holiday rental in Cookstown

Cozy & Clean upper unit

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Fully Furnished Home Exclude Basement, holiday rental in Cookstown
Cozy Fully Furnished Home Exclude Basement, holiday rental in Cookstown
Cozy Fully Furnished Home Exclude Basement, holiday rental in Cookstown

Cozy Fully Furnished Home Exclude Basement

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, holiday rental in Cookstown
Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, holiday rental in Cookstown
Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto, holiday rental in Cookstown

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Oake Room - Modern Convenience, holiday rental in Cookstown
The Oake Room - Modern Convenience, holiday rental in Cookstown
The Oake Room - Modern Convenience, holiday rental in Cookstown

The Oake Room - Modern Convenience

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cottage Close to Lake Simcoe, holiday rental in Cookstown
Cozy Cottage Close to Lake Simcoe, holiday rental in Cookstown
Cozy Cottage Close to Lake Simcoe, holiday rental in Cookstown

Cozy Cottage Close to Lake Simcoe

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious family friendly home, game room, 5 minutes from Lake Simcoe, holiday rental in Cookstown
Spacious family friendly home, game room, 5 minutes from Lake Simcoe, holiday rental in Cookstown
Spacious family friendly home, game room, 5 minutes from Lake Simcoe, holiday rental in Cookstown

Spacious family friendly home, game room, 5 minutes from Lake Simcoe

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private and spacious 1 bedroom suite with hot tub, holiday rental in Cookstown
Private and spacious 1 bedroom suite with hot tub, holiday rental in Cookstown
Private and spacious 1 bedroom suite with hot tub, holiday rental in Cookstown

Private and spacious 1 bedroom suite with hot tub

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Innisfil Adventure: Your Cozy Camper Van Getaway!, holiday rental in Cookstown
Innisfil Adventure: Your Cozy Camper Van Getaway!, holiday rental in Cookstown
Innisfil Adventure: Your Cozy Camper Van Getaway!, holiday rental in Cookstown

Innisfil Adventure: Your Cozy Camper Van Getaway!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy and Relax. A perfect place for a weekend escape from city., holiday rental in Cookstown
Cozy and Relax. A perfect place for a weekend escape from city., holiday rental in Cookstown
Cozy and Relax. A perfect place for a weekend escape from city., holiday rental in Cookstown

Cozy and Relax. A perfect place for a weekend escape from city.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Boyne River Cottage- steps to great fishing, holiday rental in Cookstown
Private Boyne River Cottage- steps to great fishing, holiday rental in Cookstown
Private Boyne River Cottage- steps to great fishing, holiday rental in Cookstown

Private Boyne River Cottage- steps to great fishing

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private farmhouse w/claw foot tubs, firepit and walking trails, holiday rental in Cookstown
Private farmhouse w/claw foot tubs, firepit and walking trails, holiday rental in Cookstown
Private farmhouse w/claw foot tubs, firepit and walking trails, holiday rental in Cookstown

Private farmhouse w/claw foot tubs, firepit and walking trails

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing cottage  very close to beautiful Simcoe Lake, holiday rental in Cookstown
Amazing cottage  very close to beautiful Simcoe Lake, holiday rental in Cookstown
Amazing cottage  very close to beautiful Simcoe Lake, holiday rental in Cookstown

Amazing cottage very close to beautiful Simcoe Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Mansion in Bradford, holiday rental in Cookstown
Luxury Mansion in Bradford, holiday rental in Cookstown
Luxury Mansion in Bradford, holiday rental in Cookstown

Luxury Mansion in Bradford

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful unique and exceptional house., holiday rental in Cookstown
Beautiful unique and exceptional house., holiday rental in Cookstown
Beautiful unique and exceptional house., holiday rental in Cookstown

Beautiful unique and exceptional house.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-45 of 45
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