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Cookstown Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Cookstown holiday rentals

Interior

1. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.4 out of 10, Very good, (6 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is HK$643
HK$1,523 total
includes taxes & fees
1 Sept - 2 Sept
Clean & Cozy Home Near Downtown
TV, fireplace

2. The Chieftain Suite

The Chieftain Suite
Barrie
9.6 out of 10, Exceptional, (17 reviews)
"Very clean and quiet place to stay! Communication was great and I was able to check in an hour early."
Canada
Kaitlyn
The price is HK$620
HK$1,198 total
includes taxes & fees
1 Sept - 2 Sept
The Chieftain Suite
TV

3. 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.
The price is HK$852
HK$1,536 total
includes taxes & fees
7 Sept - 8 Sept
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Iron/ironing board, WiFi, bed sheets

4. Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!

Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Georgina
The price is HK$1,050
HK$1,506 total
includes taxes & fees
14 Sept - 15 Sept
Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Terrace/patio

5. 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 HK$691
HK$1,902 total
includes taxes & fees
2 Sept - 3 Sept
Modern 4 Bedroom Townhouse in Barrie South
Coffee/tea maker, fridge, microwave, oven

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

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
9.0 out of 10, Wonderful, (12 reviews)
"Clean apartment, spacious, nice neighbourhood"
Canada
Peter v.
The price is HK$812
HK$1,287 total
includes taxes & fees
1 Sept - 2 Sept
New, Clean and Comfortable Apartment with Private Entrance.
Private kitchen

7. The Allandale Residence

The Allandale Residence
Barrie
9.8 out of 10, Exceptional, (16 reviews)
"Clean and comfortable house."
Canada
Karla
The price is HK$846
HK$2,179 total
includes taxes & fees
1 Sept - 2 Sept
The Allandale Residence
Living area

8. Warm & Cozy 3BR Retreat!

Warm & Cozy 3BR Retreat!
Bradford West Gwillimbury
10.0 out of 10, Exceptional, (1 review)
"Clean. As described. Perfect for what we needed.There were people outside at neighboring houses in the evening (not loud just enjoying the evening). You could not hear them inside.Know that there is one set of steps to get to the main floor and another set of steps to get to the bedroom level. Great for most people but it would be hard for some.We would stay again."
United States
Erica L.
The price is HK$1,240
HK$2,326 total
includes taxes & fees
1 Sept - 2 Sept
Warm & Cozy 3BR Retreat!
Exterior detail

9. The Luxe Haven

The Luxe Haven
East Gwillimbury
The price is HK$538
HK$2,150 total
includes taxes & fees
14 Sept - 15 Sept
The Luxe Haven
Interior

10. 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 HK$1,173
HK$2,561 total
includes taxes & fees
1 Sept - 2 Sept
Modern 2BR Smart Home, Designed for Ease—Mins to Shops, Dining & Innisfil Beach!
Beach

11. ARCA Cozy Cabin-Innisfil Beach

ARCA Cozy Cabin-Innisfil Beach
Innisfil
9.8 out of 10, Exceptional, (14 reviews)
"Great spot for families"
Canada
Lesa W.
The price is HK$1,128
HK$2,542 total
includes taxes & fees
3 Sept - 4 Sept
ARCA Cozy Cabin-Innisfil Beach
Living area

12. Family/Group: Cozy 3BR Entire Home

Family/Group: Cozy 3BR Entire Home
Bradford West Gwillimbury
The price is HK$1,663
HK$2,874 total
includes taxes & fees
12 Sept - 13 Sept
Family/Group: Cozy 3BR Entire Home
Living area

13. Cozy 3BR Cottage Near Lake Simcoe

Cozy 3BR Cottage Near Lake Simcoe
2.0 star property
Georgina
10.0 out of 10, Exceptional, (2 reviews)
"It was comfortable and cozy felt like home. Alot of beaches ,trails and shopping around."
Canada
Corinne
The price is HK$730
HK$825 total
includes taxes & fees
2 Sept - 3 Sept
Cozy 3BR Cottage Near Lake Simcoe
1 bedroom, travel cot, free WiFi, bed sheets

14. Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking

Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
Aurora
10.0 out of 10, Exceptional, (15 reviews)
"My daughter and I stayed here for one week and we had the most amazing time. The owner answered all our questions so that everything went smoothly - from the moment of check-in to how to get to the neighbourhood grocery shop. This area was very safe and quiet and most of all, this very well-kept and welcoming place made our trip so memorable and pleasurable. She even shared her fresh baked croissants with us!! We are so satisfied to be able to stay here."
Canada
Hitomi
The price is HK$677
HK$1,198 total
includes taxes & fees
9 Sept - 10 Sept
Stylish Main Level Suite with Separate Entrance, Private Patio and 2 Car Parking
Exterior

15. Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower

Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Sutton
9.6 out of 10, Exceptional, (155 reviews)
"Great get-away. The cabin was super relaxing and very private."
Canada
Jason
The price is HK$1,040
HK$1,927 total
includes taxes & fees
1 Sept - 2 Sept
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Coffee/tea maker, fridge, microwave, oven

16. 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
10.0 out of 10, Exceptional, (2 reviews)
"Nice place"
Canada
mike
The price is HK$564
HK$1,134 total
includes taxes & fees
1 Oct - 2 Oct
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Interior

17. Stylish 4BR Getaway. Family Friendly. Mins to Hwy

Stylish 4BR Getaway. Family Friendly. Mins to Hwy
Barrie
7.2 out of 10, Good, (7 reviews)
"Conveniently close to hwy, spacious but ad does not match the property. Cleanliness was not to expectations, bath towels were not fresh, amenities weren't all there (something as simple as garbage bags and dish towels) responsiveness was slow although friendly. It has such great potential if improvements are made."
United States
Kimberly B.
The price is HK$1,347
HK$3,006 total
includes taxes & fees
1 Sept - 2 Sept
Stylish 4BR Getaway. Family Friendly. Mins to Hwy
Smart TV, fireplace

18. Modern 5-bedroom house close to Ski and Forest Trails

Modern 5-bedroom house close to Ski and Forest Trails
Ardagh Bluffs
10.0 out of 10, Exceptional, (28 reviews)
"Perfect for a work crew Or a couple families for vacation"
Canada
John V.
The price is HK$1,776
HK$3,593 total
includes taxes & fees
9 Sept - 10 Sept
Modern 5-bedroom house close to Ski and Forest Trails
Smart TV

19. 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.
Wonderful place of Lake Simkoe
Terrace/patio

20. Spacious | Private | Quiet | 2 BR Walkout Suite

Spacious | Private | Quiet | 2 BR Walkout Suite
Aurora
10.0 out of 10, Exceptional, (1 review)
"This property is an amazing, family-friendly retreat located in a peaceful, quiet neighborhood. The spacious unit is impeccably clean and features a fully equipped kitchen. The host provides outstanding, responsive service, making this an ideal choice for both short-term and long-term stays. Highly recommended."
Canada
Ayla
The price is HK$558
HK$1,803 total
includes taxes & fees
2 Sept - 3 Sept
Spacious | Private | Quiet | 2 BR Walkout Suite
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

Days Inn by Wyndham Barrie

Days Inn by Wyndham Barrie

10/10 Excellent
"The room was kept clean. Just next time more shampoo and body wash. The wallpaper in the bathroom was lifted, the shower curtain looked dirty. But all, in all it was a great room and another great stay. Will definitely come back, and recommend it to my friends and family"
Rebecca 3-night trip
Posted 7 hours ago
Days Inn by Wyndham Barrie

Find out more about Cookstown

Search for holiday rentals in Cookstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Cookstown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cookstown!

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?

The Mansion, Wasaga beach, Blue mountain: This holiday home rental outside of Cookstown is located next to a golf course, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and an arcade/games room so that you can immerse yourself in your holiday.

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.