Cookstown Vacations from $418

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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.
Revery Toronto Downtown, Curio Collection by Hilton

Revery Toronto Downtown, Curio Collection by Hilton

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $618, price is now $418 per person
$418
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.6/10 Exceptional! (1,008 reviews)
I did not have the breakfast there. Everything else was awesome!

Reviewed on Jan 9, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $809, price is now $448 per person
$448
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.2/10 Wonderful! (451 reviews)
Room very modern and clean. Tons of towels and lovely amenities. Breakfast was incredible. Entire second floor buffet, very fresh and more food than anyone could eat. Will absolutely book here again.

Reviewed on Jan 10, 2026

Spacious 4-Bedroom Retreat

Spacious 4-Bedroom Retreat

3 out of 5
Save 100% on your flight
Price was $1,823, price is now $1,016 per person
$1,016
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
No reviews
1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,296, price is now $861 per person
$861
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.4/10 Exceptional! (632 reviews)
I forgot something in the room and the staff had it saved for me and returned it only if I had my ID. Terrific service I’ve been to places where they would’ve said it’s gone you forgot it but 1 Hotel Toronto cares about their clientele

Reviewed on Jan 2, 2026

Residence Inn by Marriott Toronto Downtown / Entertainment District

Residence Inn by Marriott Toronto Downtown / Entertainment District

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $734, price is now $496 per person
$496
per person
Mar 27 - Mar 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.2/10 Wonderful! (3,171 reviews)
The room is clean.My children enjoyed the pool and the food. We will definitely back someday!

Reviewed on Jan 9, 2026

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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

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

The Point Gallery

You can spend an afternoon browsing the exhibits at The Point Gallery during your trip to Big Bay Point. While in this family-friendly area, you can savor the top-notch restaurants.

The Point Gallery

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
$68 nightly
The price is $81 total per night from Jan 12 to Jan 13
$81 total
Jan 12 - Jan 13
Total with taxes and fees
8/10 Very Good! (2,446 reviews)
The trainee at the desk was excellent. Thank you :)

Reviewed on Jan 10, 2026

Monte Carlo Inn Barrie Suites
Days Inn by Wyndham Barrie

Days Inn by Wyndham Barrie

2.5 out of 5
Hart Drive,55 Barrie ON
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $66 total per night from Feb 1 to Feb 2
$66 total
Feb 1 - Feb 2
Total with taxes and fees
6.8/10 (1,140 reviews)
It was ok

Reviewed on Jan 9, 2026

Days Inn 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
$65 nightly
The price is $78 total per night from Jan 18 to Jan 19
$78 total
Jan 18 - Jan 19
Total with taxes and fees
7.6/10 Good! (1,454 reviews)
Staff

Reviewed on Jan 4, 2026

Super 8 by Wyndham Barrie South
See all 562 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.

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

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Frequently asked questions

How much does a Cookstown vacation package cost?
Offering great value package deals from $418 on Expedia, you'll be thrilled with how little a vacation to Cookstown costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Cookstown?
If you're hoping to snag a cheap Cookstown vacation package, consider visiting in December, January and February. You'll usually find better prices on accommodations and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Cookstown?
Usually, a handful of days is enough to explore the main attractions during your Cookstown vacation. But if you prefer to have more time to relax or go on day tours, think about extending your itinerary.
Is it worth booking a vacation package to Cookstown?
It's easy to see why a Cookstown vacation is on the to-do list of many travelers. Leading attractions like Tanger Outlets are just the start of things to keep you busy here.
How to find the best Cookstown package deals?
Use Expedia's filter tool to find some fabulous Cookstown package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Cookstown package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Cookstown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can customize your Cookstown trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Cookstown?
If you have your Cookstown travel dates finalized, book as soon as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Cookstown vacation packages?
Your Cookstown trip should be an escape from your busy life, not a reason for money worries. So to give you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.