Cookstown Vacation Rentals from $110: Search Short-Term Rentals

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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

New Tecumseth

Suzanne

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

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

Bond head

A A.

$170 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern living room with a dining area, featuring a green wall with a neon sign, a chandelier, and a view of the city through large windows.

3. Bright 3BR Home with Balcony & Free Parking

Bradford West Gwillimbury

Stephan

$222 nightly

Oct 22 - Oct 23

Total with taxes and fees

A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

4. Modern 4 Bedroom Townhouse in Barrie South

Painswick

Patrick K.

$218 nightly

Oct 19 - Oct 20

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a black sink.

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

East Gwillimbury

Kwame A.

$143 nightly

Oct 18 - Oct 19

Total with taxes and fees

A living room with a white sofa, a coffee table with a glass bowl, and a flat-screen TV on a stand.

6. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Innisfil

Ashna

$237 nightly

Oct 19 - Oct 20

Total with taxes and fees

A two-story house with a garage, double doors, and a nameplate reading "247 Walter English Drive".

7. The Luxe Haven

East Gwillimbury

$229 nightly

Oct 27 - Oct 28

Total with taxes and fees

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.

8. Crazy Farm C-Can Chalet

Innisfil

Hannah

$98 nightly

Nov 1 - Nov 2

Total with taxes and fees

A living room with a sofa, armchair, glass coffee table, and a flat-screen TV.

9. Wonderful place of Lake Simkoe

Innisfil

William O.

$231 nightly

Oct 18 - Oct 19

Total with taxes and fees

A modern kitchen with dark cabinets, a stainless steel oven, and a granite countertop.

10. Innisfil Getaway

Innisfil

$281 nightly

Oct 19 - Oct 20

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

11. West Oak @ Barrie H&ME Tech Build

Barrie

"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!"

Rhea T.

$427 nightly

Oct 21 - Oct 22

Total with taxes and fees

12. Utopia villa and spa

Innisfil

Krista K.

$425 nightly

Oct 21 - Oct 22

Total with taxes and fees

A beach with a blue mat leading to the water, clear skies, and a distant pier.

13. ARCA Cozy Cabin-Innisfil Beach

Innisfil

Joanna H.

$243 nightly

Nov 1 - Nov 2

Total with taxes and fees

14. Brand New! Luxury Retreat!

Barrie

bob g.

$409 nightly

Oct 19 - Oct 20

Total with taxes and fees

A modern kitchen with stainless steel appliances, dark cabinetry, and a wine rack.

15. Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups

Gilford

zeshan r.

$1,437 nightly

Oct 18 - Oct 19

Total with taxes and fees

Sit back and relax in our spacious living room, featuring a 3-seater couch, a solo seat, a coffee table, and a smart TV. This area also features a wide window and a sliding glass door for a bright and refreshing environment.

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

Barrie

Kimberly B.

A bedroom with a bed, a flat-screen TV mounted on the wall, and a beach scene painting.

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

Ardagh Bluffs

$203 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with stainless steel appliances, a microwave, oven, and a refrigerator.

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

Kettleby, King City

"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....

Frank

$129 nightly

Oct 18 - Oct 19

Total with taxes and fees

A modern living room with a wooden dining table, a sofa, and a television.

19. Bright 2 Bedroom Entire Basement Apartment

Angus

Adriano A.

$196 nightly

Oct 18 - Oct 19

Total with taxes and fees

A clear river with visible rocks and trees on the banks.

20. Cozy Cottage Across Lake Simcoe

Innisfil

Michael P.

$348 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Cookstown Hotel Reviews

Holiday Inn Express & Suites Aurora by IHG

10/10 Excellent

"The front desk staff were very nice and helpful. I enjoyed the breakfast as an option instead of going out - although you could have bacon everyday lol! My room was so spacious and very clean. I appreciated the free parking. The location is good as it's right by the highway. I was on the end of the hotel closest to the highway and it was loud however I wore earplugs and I slept well. The blinds are very good for darkening the room. There is ample space for all your belongings. If you have the do not disturb sign on your door all day, they slip a card underneath which shows when they stopped by and if you need anything just ring the front desk. I love that! I would definitely stay here again."

The Postmark Hotel

8/10 Good

"I recently stayed in one of the lower rooms with a patio; unfortunately it was right next to the main fans etc from the restaurant so rather noisy. Parking was rather chaotic, as in first being told to park in a particular spot during my 3-night stay, only to return one evening to find my spot was taken. I was then told to take any of the reserved spots. The hotel was kind enough to reverse any parking charges and I can only assume that this is why. Staff were friendly and accommodating. Wish"

Best Western Plus Barrie

10/10 Excellent

"Fantastic Thanksgiving stay! The room was spotless, the hotel was well-maintained, and the customer service was excellent. The location right off the highway was super convenient, and free parking was great. The complimentary breakfast really stood out—having bacon, omelettes, fresh scrambled eggs, and delicious coffee is a rare treat for a complimentary breakfast. My wife and I thoroughly enjoyed our time here and will definitely return next time we're in the area."

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 $110 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.

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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 rental 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.

Cookstown Vacation Rentals

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Check prices for these dates

Our top choices for Cookstown vacation rentals

1. Clean & Cozy Home Near Downtown

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

3. Bright 3BR Home with Balcony & Free Parking

4. Modern 4 Bedroom Townhouse in Barrie South

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

6. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

7. The Luxe Haven

8. Crazy Farm C-Can Chalet

9. Wonderful place of Lake Simkoe

10. Innisfil Getaway

11. West Oak @ Barrie H&ME Tech Build

12. Utopia villa and spa

13. ARCA Cozy Cabin-Innisfil Beach

14. Brand New! Luxury Retreat!

15. Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups

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

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

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

19. Bright 2 Bedroom Entire Basement Apartment

20. Cozy Cottage Across Lake Simcoe

Find vacation rentals that suit your style

Top Cookstown Hotel Reviews

Holiday Inn Express & Suites Aurora by IHG

Find out more about Cookstown

Explore a world of travel with Expedia

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