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Cookstown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cookstown vacation rentals

A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

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
$170 nightly
The price is $192
Sep 24 - Sep 25
Total with taxes and fees
Clean & Cozy Home Near Downtown
A modern living room with a sofa, a TV, and large windows.

2. 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.
$171 nightly
The price is $194
Sep 30 - Oct 1
Total with taxes and fees
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
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.

3. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.4 out of 10, Very good, (5 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
$112 nightly
The price is $127
Sep 24 - Sep 25
Total with taxes and fees
Crazy Farm C-Can Chalet
A modern living room with a grey sofa, a flat-screen TV mounted on the wall, and a wooden coffee table.

4. 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
$134 nightly
The price is $151
Sep 24 - Sep 25
Total with taxes and fees
The Chieftain Suite
A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

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.
$221 nightly
The price is $250
Sep 24 - Sep 25
Total with taxes and fees
Modern 4 Bedroom Townhouse in Barrie South
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
9.0 out of 10, Wonderful, (12 reviews)
"easy to check in and a great place to stay! very helpful hosts."
United States
Kwame A.
$144 nightly
The price is $162
Sep 26 - Sep 27
Total with taxes and fees
New, Clean and Comfortable Apartment with Private Entrance.
A modern kitchen with white cabinetry, a black refrigerator, a stove, and a microwave.

7. The Allandale Residence

The Allandale Residence
Barrie
9.8 out of 10, Exceptional, (17 reviews)
"Clean and comfortable house."
Canada
Karla
$244 nightly
The price is $276
Sep 29 - Sep 30
Total with taxes and fees
The Allandale Residence
A modern living room with a white sofa, a glass coffee table with wooden blocks, a remote control, and a flat-screen TV displaying various videos.

8. 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
$238 nightly
The price is $269
Sep 24 - Sep 25
Total with taxes and fees
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
A bedroom with a bed, two bedside tables, and a window with blinds.

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

Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Georgina
10.0 out of 10, Exceptional, (1 review)
"The amenities of this property were amazing. The outdoor entertainment area with home theatre, hot tub, sauna and peaceful garden was fantastic It was a true gem, happy that I experienced with my family’s This is perfect for couple getaway or a girls trip! Highly recommend!"
Canada
Sorina
$235 nightly
The price is $266
Sep 24 - Sep 25
Total with taxes and fees
Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
A modern living room with a glass coffee table, two armchairs, a sofa, a wall-mounted neon sign, and a framed picture.

10. Bright 3BR Home with Balcony & Free Parking

Bright 3BR Home with Balcony & Free Parking
Bradford West Gwillimbury
$244 nightly
The price is $275
Sep 28 - Sep 29
Total with taxes and fees
Bright 3BR Home with Balcony & Free Parking
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

11. 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, (3 reviews)
"This place was immaculate. Host was always super responsive. Had everything we needed. Highly recommend. We really enjoyed our stay."
Canada
Jennifer
$191 nightly
The price is $216
Sep 30 - Oct 1
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

12. 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.
$414 nightly
The price is $468
Sep 24 - Sep 25
Total with taxes and fees
West Oak @ Barrie H&ME Tech Build
A living room with a sofa, armchair, glass coffee table, and a flat-screen TV.

13. 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.
$232 nightly
The price is $262
Sep 30 - Oct 1
Total with taxes and fees
Wonderful place of Lake Simkoe
A two-story house with a garage, double doors, and a nameplate reading "247 Walter English Drive".

14. The Luxe Haven

The Luxe Haven
East Gwillimbury
$228 nightly
The price is $257
Sep 24 - Sep 25
Total with taxes and fees
The Luxe Haven
A beach with a clear sky and calm sea.

15. Brand New! Luxury Retreat!

Brand New! Luxury Retreat!
Barrie
10.0 out of 10, Exceptional, (10 reviews)
"It was an excellent place to stay, Hosts are nice and even give us some welcome gifts"
Canada
bob g.
$423 nightly
The price is $478
Sep 30 - Oct 1
Total with taxes and fees
Brand New! Luxury Retreat!
A modern kitchen with dark cabinets, a stainless steel oven, and a granite countertop.

16. Innisfil Getaway

Innisfil Getaway
Innisfil
$282 nightly
The price is $318
Sep 25 - Sep 26
Total with taxes and fees
Innisfil Getaway
A living room with a flat-screen TV mounted on the wall, a black sectional sofa with cushions, a white coffee table with a tray, and a painting of a beach scene.

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

Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
Ardagh Bluffs
$219 nightly
The price is $247
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Parkside End Unit | 3 Bedrooms | Sleeps 8
A modern hotel with a rooftop pool and outdoor seating area.

18. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
$271 nightly
The price is $294
Sep 25 - Sep 26
Total with taxes and fees
Upscale Spa Getaway w/ Private Sauna
A modern lodge with a large glass facade, a waterfall feature, and a covered outdoor seating area.

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

Stylish & Modern House ♥ Walking distance to Barrie Beach!
Barrie
6.0 out of 10, (1 review)
$171 nightly
The price is $193
Sep 29 - Sep 30
Total with taxes and fees
Stylish & Modern House ♥ Walking distance to Barrie Beach!
A modern kitchen with stainless steel appliances, white cabinetry, and a central island with bar stools.

20. Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus
Angus
9.2 out of 10, Wonderful, (9 reviews)
"Hassan was a fabulous host and the place was a great stay for our group! Would use again!"
Canada
Jesse
$226 nightly
The price is $256
Sep 24 - Sep 25
Total with taxes and fees
Spacious 4 Bedroom House in Angus
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

Ramada by Wyndham Jacksons Point

Ramada by Wyndham Jacksons Point

8/10 Good
"The outside facade needs a little TLC but overall very nice. The staff were very helpful getting all our groups needs during the AGM. The rooms were clean and comfortable. The food supplied was good and plentiful. Some folks used the spa for a massage and said it was very good. The pool area was clean and ample towels to use for both the pool and Hot tub. The gym is a little small but sufficed for those who used it."
Brian 2-night trip
Posted 6 hours ago
Ramada by Wyndham Jacksons Point

Find out more about Cookstown

Everything you need to know about Cookstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cookstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cookstown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cookstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $231 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cookstown rentals

At Expedia, we put the best Cookstown vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Cookstown?

Yes, you can find vacation rentals near the most popular attractions in Cookstown, or you can select a more remote option if you're looking for a relaxing stay. Cookstown is known for its golf courses and shopping.

What's the top vacation rental that Cookstown has to offer?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This vacation home near Cookstown is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a 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 vacation rental in Cookstown like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Cookstown. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.