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Cookstown Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Cookstown holiday rentals

A modern living room with a sofa, a TV, and large windows.

1. Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful

Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Bond head
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and the host was very accommodating. One of the best places to stay in the area."
United States
A A.
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
A modern interior with a staircase leading to a dining area, a kitchen with contemporary appliances, and a decorative wall piece.

2. Bright 3BR Home with Balcony & Free Parking

Bright 3BR Home with Balcony & Free Parking
Bradford West Gwillimbury
10.0 out of 10, Exceptional, (1 review)
"Couldn’t have asked for a better place to stay while attending a wedding in Cookstown. The response rate was amazing along with the host who was flexible in accommodatable based off of our requests. 10/10 would stay again!"
Canada
Stephan
Bright 3BR Home with Balcony & Free Parking
A modern living room with a sectional sofa, a round coffee table, and a kitchen in the background.

3. The Scarlet Retreat | Spacious 2BR Suite

The Scarlet Retreat | Spacious 2BR Suite
Bradford West Gwillimbury
The price is AU$369
includes taxes & fees
23 Oct - 24 Oct
The Scarlet Retreat | Spacious 2BR Suite
A cozy living room with a brown sofa, a coffee table, and a TV. There's a kitchen area with a fridge and a sink in the background.

4. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is AU$161
includes taxes & fees
3 Nov - 4 Nov
Crazy Farm C-Can Chalet
A two-story house with a garage, double doors, and a nameplate reading "247 Walter English Drive".

5. The Luxe Haven

The Luxe Haven
East Gwillimbury
The price is AU$367
includes taxes & fees
29 Oct - 30 Oct
The Luxe Haven
A modern kitchen with white cabinets, stainless steel appliances, and a black sink.

6. New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
8.6 out of 10, Excellent, (13 reviews)
"easy to check in and a great place to stay! very helpful hosts."
United States
Kwame A.
New, Clean and Comfortable Apartment with Private Entrance.
A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

7. Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Painswick
9.0 out of 10, Wonderful, (21 reviews)
"Was great!"
Canada
Patrick K.
The price is AU$335
includes taxes & fees
25 Oct - 26 Oct
Modern 4 Bedroom Townhouse in Barrie South
A modern kitchen with a double sink, a dish rack, and a countertop with kitchen essentials.

8. Modern 2BR Smart Home, Designed for Ease—Mins to Shops, Dining & Innisfil Beach!

Modern 2BR Smart Home, Designed for Ease—Mins to Shops, Dining & Innisfil Beach!
Innisfil
9.2 out of 10, Wonderful, (5 reviews)
"We had a great trip! The place was very clean and the host was easy to contact. It was also right next to a plaza with a No Frills and many other places to eat."
Canada
Isabella S.
The price is AU$437
includes taxes & fees
23 Oct - 24 Oct
Modern 2BR Smart Home, Designed for Ease—Mins to Shops, Dining & Innisfil Beach!
A living room with a white sofa, a coffee table with a glass bowl, and a flat-screen TV on a stand.

9. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
Innisfil
8.0 out of 10, Very good, (2 reviews)
"The host is so awesome! They sent me a professional booklet before my stay. All questions answered promptly. I would recommend them again and again!!!"
Canada
Ashna
The price is AU$415
includes taxes & fees
23 Oct - 24 Oct
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
A living room with a sofa, armchair, glass coffee table, and a flat-screen TV.

10. Wonderful place of Lake Simkoe

Wonderful place of Lake Simkoe
Innisfil
8.8 out of 10, Excellent, (8 reviews)
"We only stayed 1 night but it was perfect "
Canada
William O.
The price is AU$373
includes taxes & fees
23 Oct - 24 Oct
Wonderful place of Lake Simkoe
A bedroom with a bed, a flat-screen TV mounted on the wall, and a beach scene painting.

11. Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8

Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
Ardagh Bluffs
The price is AU$331
includes taxes & fees
2 Nov - 3 Nov
Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
A beach with a blue mat leading to the water, clear skies, and a distant pier.

12. ARCA Cozy Cabin-Innisfil Beach

ARCA Cozy Cabin-Innisfil Beach
Innisfil
9.4 out of 10, Exceptional, (18 reviews)
"Our family of 4 really enjoyed our stay! It's a short walk or drive to a private beach. We loved watching the ducks and geese on the water. Wifi worked well and the cabin was well stocked with cooking utensils. I would recommend!"
United States
Joanna H.
The price is AU$392
includes taxes & fees
1 Nov - 2 Nov
ARCA Cozy Cabin-Innisfil Beach
A modern kitchen with stainless steel appliances, a microwave, oven, and a refrigerator.

13. Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400

Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Kettleby, King City
7.0 out of 10, Good, (4 reviews)
"Owners were very nice. Told us to reach out if we needed anything. She offered to help us with our luggage. Very sweet. Even though we were forewarned about the sound of the pump in washroom, we weren’t expecting it to be that loud and running that often. The washroom is right behind the bed, so it will wake you up. The place was pretty clean, except the washroom and the entrance. Bed was comfortable and floors were clean. Location was great for where we needed to be. Beautiful neighbourhood....
Canada
Frank
The price is AU$212
includes taxes & fees
23 Oct - 24 Oct
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
A modern living room with a wooden dining table, a sofa, and a television.

14. Bright 2 Bedroom Entire Basement Apartment

Bright 2 Bedroom Entire Basement Apartment
Angus
9.0 out of 10, Wonderful, (13 reviews)
"Great place"
United States
Adriano A.
The price is AU$311
includes taxes & fees
2 Nov - 3 Nov
Bright 2 Bedroom Entire Basement Apartment
A modern kitchen with stainless steel appliances, white cabinetry, and a central island with bar stools.

15. Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus
Angus
9.0 out of 10, Wonderful, (11 reviews)
"Hassan was a fabulous host and the place was a great stay for our group! Would use again!"
Canada
Jesse
The price is AU$355
includes taxes & fees
25 Oct - 26 Oct
Spacious 4 Bedroom House in Angus
A modern kitchen with dark cabinets, a stainless steel oven, and a granite countertop.

16. Innisfil Getaway

Innisfil Getaway
Innisfil
The price is AU$451
includes taxes & fees
26 Oct - 27 Oct
Innisfil Getaway
A modern lodge with a large glass facade, a waterfall feature, and a covered outdoor seating area.

17. Stylish & Modern House ♥ Walking distance to Barrie Beach!

Stylish & Modern House ♥ Walking distance to Barrie Beach!
Barrie
6.0 out of 10, (1 review)
The price is AU$276
includes taxes & fees
25 Oct - 26 Oct
Stylish & Modern House ♥ Walking distance to Barrie Beach!
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

18. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (4 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
Canada
lisa
The price is AU$308
includes taxes & fees
25 Oct - 26 Oct
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A wooden interior with a high ceiling, a wooden table with two chairs, and a small potted plant.

19. Utopia villa and spa

Utopia villa and spa
Innisfil
10.0 out of 10, Exceptional, (11 reviews)
"The hosts were very accommodating and communication was good. The outside of the property is VERY deceiving but once inside it is beautiful and very cozy."
Canada
Krista K.
The price is AU$658
includes taxes & fees
3 Nov - 4 Nov
Utopia villa and spa
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

20. West Oak @ Barrie H&ME Tech Build

West Oak @ Barrie H&ME Tech Build
Barrie
10.0 out of 10, Exceptional, (1 review)
"We had a group of five staying here, and it was great to have enough bedrooms and bathrooms for everyone. The house was clean, spacious, and comfortable. The owner was very responsive to our messages and answered all of our questions promptly. We would definitely look to book this house again, as it worked very well for our larger group and was conveniently located near the Barrie Ice Arena. Everyone had a great stay!"
United States
Rhea T.
The price is AU$686
includes taxes & fees
26 Oct - 27 Oct
West Oak @ Barrie H&ME Tech Build
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cookstown Hotel Reviews

Travelodge by Wyndham Barrie

Travelodge by Wyndham Barrie

8/10 Good
"The hotel is very central and acess to the 400 perfect. The continental breakfast was well stocked with choices."
David 3-night trip
Posted 15 hours ago
Travelodge by Wyndham Barrie

Find out more about Cookstown

Everything you need to know about Cookstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cookstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cookstown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cookstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cookstown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cookstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cookstown holiday rentals we have selected for you start as low as AU$161 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cookstown rentals

At Expedia, we put the best Cookstown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cookstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cookstown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cookstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cookstown?

Yes, there are holiday rentals close to the most popular sights in Cookstown, or you can select a more secluded option if you're looking for a relaxing stay. Cookstown is known for its golf courses and shopping.

What are some of the best holiday rentals that Cookstown has to offer?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This holiday home rental outside of Cookstown is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What’s there to see and do in Cookstown?

Explore the area and family-friendly sights such as Splashon Water Park Barrie, or get out into nature at a spot like Holland Marsh. Tanger Outlets and Innisfil Creek Golf Course are other places to visit while you're in town.

What’s a holiday rental in Cookstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cookstown. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.