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Cookstown Holiday Rentals

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49 rentals in Cookstown.
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**Water Front** Duck Lake Guest House, holiday rental in Cookstown

**Water Front** Duck Lake Guest House

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Family-Friendly Cottage on Lake Simcoe with Private Shared Beach Access, holiday rental in Cookstown

Family-Friendly Cottage on Lake Simcoe with Private Shared Beach Access

4 bedrooms
2 bathrooms
Sleeps 8
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Peaceful Cottage Close To Innisfil Beach, holiday rental in Cookstown

Peaceful Cottage Close To Innisfil Beach

4 bedrooms
2 bathrooms
Sleeps 10
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Lakeside getaway on the shores of Lake Simcoe, holiday rental in Cookstown

Lakeside getaway on the shores of Lake Simcoe

1 bedroom
2 bathrooms
Sleeps 2
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Luxury Lakeside Executive Suite, holiday rental in Cookstown

Luxury Lakeside Executive Suite

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Barrie house close to all amenities, holiday rental in Cookstown

Barrie house close to all amenities

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Simcoe Waterfront Getaway, holiday rental in Cookstown

Lake Simcoe Waterfront Getaway

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Country Cabin for Stays - WE ACCEPT BOOKINGS - Near Newmarket Toronto, holiday rental in Cookstown

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Newly renovated Cozy Cottage with a Condo feel!, holiday rental in Cookstown

Newly renovated Cozy Cottage with a Condo feel!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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!!Beautiful Resort Condo * Friday Harbour Resort!!, holiday rental in Cookstown

!!Beautiful Resort Condo * Friday Harbour Resort!!

2 bedrooms
1 bathroom
Sleeps 4
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Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - near Toronto Newmarket, holiday rental in Cookstown

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

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Luxurious Lake front Island Twnhome Friday Harbour, holiday rental in Cookstown

Luxurious Lake front Island Twnhome Friday Harbour

4 bedrooms
5 bathrooms
Sleeps 16
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The North Shore Suite **IR Friendly**, holiday rental in Cookstown

The North Shore Suite **IR Friendly**

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charlotte's Cottage-Lake Simcoe, holiday rental in Cookstown

Charlotte's Cottage-Lake Simcoe

2 bedrooms
2 bathrooms
Sleeps 6
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NEWMARKET - 30 minutes north of Toronto near Ontario's vacationland!, holiday rental in Cookstown

NEWMARKET - 30 minutes north of Toronto near Ontario's vacationland!

1 bedroom
2 bathrooms
Sleeps 9
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Lakefront Cottage 1-hour north of Toronto, holiday rental in Cookstown

Lakefront Cottage 1-hour north of Toronto

3 bedrooms
1 bathroom
Sleeps 6
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Rustic Loft in Working Horse Barn- Laurenwood Farm, holiday rental in Cookstown

Rustic Loft in Working Horse Barn- Laurenwood Farm

1 bedroom
1 bathroom
Sleeps 5
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Alfa getaway (  Best View ), holiday rental in Cookstown

Alfa getaway ( Best View )

1 bedroom
1 bathroom
Sleeps 3
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Barrie. Very very private 4 acres, Whole Property, holiday rental in Cookstown

Barrie. Very very private 4 acres, Whole Property

4 bedrooms
2 bathrooms
Sleeps 16
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Stunning 10 Acre Estate With Pool 1hr from Toronto, holiday rental in Cookstown

Stunning 10 Acre Estate With Pool 1hr from Toronto

5 bedrooms
5 bathrooms
Sleeps 11
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Rustic-Chic Foxglove Farm - 1hr from Toronto, holiday rental in Cookstown

Rustic-Chic Foxglove Farm - 1hr from Toronto

4 bedrooms
3 bathrooms
Sleeps 7
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Cozy Country Getaway or Stay - WE ACCEPT BOOKINGS - Near Toronto Newmarket, holiday rental in Cookstown

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

1 bedroom
1 bathroom
Sleeps 2
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Jecara Farms - Raven Cabin, holiday rental in Cookstown

Jecara Farms - Raven Cabin

1 bedroom
2 bathrooms
Sleeps 2
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Carriage Hills Resort Two-Bedroom Suite, holiday rental in Cookstown

Carriage Hills Resort Two-Bedroom Suite

2 bedrooms
2 bathrooms
Sleeps 8
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Furnished modern 2 bedroom executive lease, holiday rental in Cookstown

Furnished modern 2 bedroom executive lease

2 bedrooms
1 bathroom
Sleeps 3
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Cozy Cottage, holiday rental in Cookstown

Cozy Cottage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Jecara Farms - Bear Cabin, holiday rental in Cookstown

Jecara Farms - Bear Cabin

1 bedroom
1 bathroom
Sleeps 4
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Jecara Farms - Snake Cabin, holiday rental in Cookstown

Jecara Farms - Snake Cabin

1 bedroom
2 bathrooms
Sleeps 2
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3 Bedroom Furnished Apartment, holiday rental in Cookstown

3 Bedroom Furnished Apartment

3 bedrooms
1 bathroom
Sleeps 5
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South Side Bed and Breakfast, holiday rental in Cookstown

South Side Bed and Breakfast

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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SHABBY SHACK ( glamping), holiday rental in Cookstown

SHABBY SHACK ( glamping)

1 bedroom
1 bathroom
Sleeps 2
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Vacation/short/long term rental, holiday rental in Cookstown

Vacation/short/long term rental

5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Luxury Accommodation At A Reasonable Price, holiday rental in Cookstown

Luxury Accommodation At A Reasonable Price

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Camp Site in the GTA w/ Optional Tent / Gear - 1, holiday rental in Cookstown

Camp Site in the GTA w/ Optional Tent / Gear - 1

1 bedroom
1 bathroom
Sleeps 50
Match: Sleeps
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Camp Site in the GTA w/ Optional Tent / Gear - 2, holiday rental in Cookstown

Camp Site in the GTA w/ Optional Tent / Gear - 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Holiday Christmas Event Hosting Space in Country, holiday rental in Cookstown

Holiday Christmas Event Hosting Space in Country

1 bedroom
1 bathroom
Sleeps 40
Match: Sleeps
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Tex’s Beautiful Cottage & Private Beach, holiday rental in Cookstown

Tex’s Beautiful Cottage & Private Beach

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Country Retreat on Horse Farm, holiday rental in Cookstown

Country Retreat on Horse Farm

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bright and charming family house in Innisfil, holiday rental in Cookstown

Bright and charming family house in Innisfil

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Unique Zen Den Guest Suite In Alliston, holiday rental in Cookstown

Unique Zen Den Guest Suite In Alliston

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Unique Country Barn Studio, holiday rental in Cookstown

Unique Country Barn Studio

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Cottage Near Barrie, holiday rental in Cookstown

Lakefront Cottage Near Barrie

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Premium Apartment w/ Kitchen, Garden Views & Off Street Parking!, holiday rental in Cookstown

Premium Apartment w/ Kitchen, Garden Views & Off Street Parking!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy & Bright Suite w/ Heated Floors, Gas Fireplace, and Spacious Backyard!, holiday rental in Cookstown

Cozy & Bright Suite w/ Heated Floors, Gas Fireplace, and Spacious Backyard!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Bright & Airy Second Floor Apartment with Lovely Backyard & Off Street Parking!, holiday rental in Cookstown

Bright & Airy Second Floor Apartment with Lovely Backyard & Off Street Parking!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Garden Suite with Soaker Tub, Spacious Backyard & Off Street Parking!, holiday rental in Cookstown

Luxury Garden Suite with Soaker Tub, Spacious Backyard & Off Street Parking!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage in Lake Simcoe/5 Bedrooms/10 Guests, holiday rental in Cookstown

Cottage in Lake Simcoe/5 Bedrooms/10 Guests

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Barrie North Retreat, holiday rental in Cookstown

Barrie North Retreat

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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★5 Minutes From Beach★ Bungalow+Garden,BBQ,Parking, holiday rental in Cookstown

★5 Minutes From Beach★ Bungalow+Garden,BBQ,Parking

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Brand New Rental Room available in South Barrie, holiday rental in Cookstown

A Brand New Rental Room available in South Barrie

1 bedroom
1 bathroom
Sleeps 1
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