We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cookstown Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
49 rentals in Cookstown.
Sort by:
Tripadvisor Sort

**Water Front** Duck Lake Guest House

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection

Rustic-Chic Foxglove Farm only 1hr from Toronto

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Large Estate-Family Vacations, Photo-shoots & Retreats

Rental Home
9 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Peaceful Cottage Close To Innisfil Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

6 Bedroom Executive Cottage near Innisfil Beach

Rental Home
6 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Barrie house close to all amenities

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Dream House by Lake Simcoe beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Luxury Lakeside Executive Suite

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Save time - get the best Cookstown rentals sent straight to your email!

Newly renovated Cozy Cottage with a Condo feel!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

Charlotte's Cottage-Lake Simcoe

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

Barrie. Very very private 4 acres, Whole Property

Rental Home
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Payment Protection

Cottage with hot tub and sauna

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

South Side Bed and Breakfast

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Rental Home
1 bedroom
1 bathroom
Sleeps 50
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection

Tex’s Beautiful Cottage & Private Beach

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection

Country Retreat on Horse Farm

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection

A Luxurious Home Away

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

4 Bedrooms beautiful, elegant house

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Harbour Haven! Waterfront escape at Friday Harbour resort

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Bright and charming family house in Innisfil

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

Unique Zen Den Guest Suite In Alliston

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

1 Bedroom 1 Bathroom

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Bright & Stylish Home in the Heart of Newmarket

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Mediterranean Country Villa

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Peaceful Retreat at Story Book Meadows near Alliston

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

BEAUTIFUL FOUR SEASON WATERFRONT COTTAGE

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Vista Park View House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy 1bedroom basement apartment with seperate entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

3 Bedroom Bungalow With Farm & Pond Near Innisfil Beach

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Unique Country Barn Studio

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

COZY 3 BDR MAIN FLOOR Newmarket

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

NICE BUNGALOW NEAR TORONTO

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

LUXURY NEWLY BUILT BEAUTIFUL HOME

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Comfortable Vacation Getaway in Innisfil Ontario.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection

Cottage in Lake Simcoe/5 Bedrooms/10 Guests

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection

Barrie North Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

Vacation home by Lake Simcoe

Rental Home
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Chalet Ewart by the lake

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy Lakehouse

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Walk to Barrie waterfront trails and downtown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 1
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1
Frequently Asked Questions about Cookstown