Cookstown Vacations from $539

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Your Cookstown Vacation

The vibrant city of Cookstown is calling. Discover all its secrets with a Cookstown vacation package that's custom made for you. If your trip to Cookstown includes a little sightseeing, hit up well-known attractions like 400 Market, Tanger Outlets and OLG Slots at Georgian Downs. Expedia can help you escape your routine. Tailor your vacation to Cookstown to suit your style of travel, whatever that may be.

The Latest Cookstown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Spacious 4-Bedroom Retreat

Spacious 4-Bedroom Retreat

3 out of 5
Save 100% on your flight
Price was $1,026, price is now $539 per person
$539
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
No reviews
12 York by CN tower

12 York by CN tower

2 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,994, price is now $1,825 per person
$1,825
per person
Dec 22 - Dec 29
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
10/10 Exceptional! (1 review)
Easy key pickup and convient

Reviewed on Oct 4, 2025

GLOBALSTAY Modern Lillian St Apartments

GLOBALSTAY Modern Lillian St Apartments

4.5 out of 5
Old Toronto
Save 100% on your flight
Price was $2,196, price is now $1,366 per person
$1,366
per person
Dec 22 - Dec 29
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
7.2/10 Good! (117 reviews)
Absolutely amazing property, very well furnished and equipped with everything you need. They took care even of the forgotten toothbrush and paste for you - the cupboards were stuffed with everything you need for a great enjoyable stay! Grocery store with delicious ready to eat hot meals righ around the corner, close to subway, landmarks, restaurants, parks, pedestrian areas. We would come back again!

Reviewed on Oct 5, 2025

GLOBALSTAY. Modern North York Condos

GLOBALSTAY. Modern North York Condos

4 out of 5
North York
Save 100% on your flight
Price was $2,158, price is now $1,348 per person
$1,348
per person
Dec 22 - Dec 29
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
6.8/10 (151 reviews)
It is a good place to stay and family friendly.

Reviewed on Sep 17, 2025

Canada Suites on Bay

Canada Suites on Bay

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,347, price is now $1,470 per person
$1,470
per person
Dec 22 - Dec 29
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (304 reviews)
Was a very nice room and easy to come and go. However the fire alarm got pulled at 3am on my second last night there and not because of a fire. I then couldn't go back to bed and was super tired for my meetings the next day.

Reviewed on Jun 9, 2025

Find the Best Cookstown Vacation Packages

Cookstown Essential Information

Language
English
Currency
Canadian dollars
Population
1,200
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
400 Market, OLG Slots at Georgian Downs and Innisfil Creek Golf Course

Cookstown Hotel Deals

Monte Carlo Inn Barrie Suites

Monte Carlo Inn Barrie Suites

3 out of 5
81 Hart Dr, Barrie, ON
Fully refundableReserve now, pay when you stay
8/10 Very Good! (2,213 reviews)
"Have stayed here before and always found it to be clean and convenient to stay"

Reviewed on Oct 1, 2025

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Monte Carlo Inn Barrie Suites
Travelodge by Wyndham Barrie

Travelodge by Wyndham Barrie

2 out of 5
300 Bayfield St, Barrie, ON
Fully refundableReserve now, pay when you stay
7.6/10 Good! (1,842 reviews)
"Good"

Reviewed on Oct 5, 2025

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Travelodge by Wyndham Barrie
Super 8 by Wyndham Barrie South

Super 8 by Wyndham Barrie South

2 out of 5
441 Bryne Drive, Barrie, ON
Fully refundableReserve now, pay when you stay
7.6/10 Good! (1,405 reviews)
"Convenient and easy access"

Reviewed on Sep 30, 2025

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Super 8 by Wyndham Barrie South
See all 548 properties in Cookstown
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cookstown

Georgian Downs Racetrack

You can take time to visit Georgian Downs Racetrack during your travels to Innisfil. While in this family-friendly area, you can savor the top-notch restaurants.

Georgian Downs Racetrack

OLG Slots at Georgian Downs

Why not try your luck with a visit to OLG Slots at Georgian Downs during your time in Innisfil? While in this family-friendly area, you can savor the top-notch restaurants.

OLG Slots at Georgian Downs

Big Cedar Golf Club

Enjoy a round of golf in Innisfil at Big Cedar Golf Club. While in this family-friendly area, you can savor the top-notch restaurants.

Big Cedar Golf Club
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.