Cookstown Vacations from $379

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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.
The Laundry Rooms Station Park Kitchener

The Laundry Rooms Station Park Kitchener

2 out of 5
K-W Hospital
Price was $504, price is now $379 per person
$379
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9.2/10 Wonderful! (367 reviews)
Convenient location...very clean. Great place to stay

Reviewed on Feb 20, 2026

Four Seasons Hotel Toronto

Four Seasons Hotel Toronto

5 out of 5
Old Toronto
Save 100% on your flight
Price was $3,094, price is now $2,027 per person
$2,027
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.6/10 Exceptional! (835 reviews)
Our stay at Four Seasons Toronto was everything you hope for when traveling as a family of five. From the moment we arrived, the team was responsive, warm, and genuinely attentive. The personalized touches made it special. Gifts for the kids, handwritten notes, champagne and chocolate waiting for us, along with fresh fruit and snacks. It truly felt like a home away from home. The chat system and seamless online ordering made everything effortless, and every staff member we encountered was friendly and accommodating. The restaurants were excellent, and the food did not disappoint. We could not have asked for a better experience. Four Seasons continues to be our family’s favorite for a reason.

Reviewed on Feb 22, 2026

The Waterside Inn

The Waterside Inn

3.5 out of 5
Port Credit
Price was $1,081, price is now $765 per person
$765
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.4/10 Very Good! (1,001 reviews)
Amazing little spot!

Reviewed on Feb 27, 2026

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Price was $615, price is now $460 per person
$460
per person
May 10 - May 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (2,077 reviews)
The room was so big, so spacious and very comfortable, the staff was so kind and helpful and the atmosphere was very romantic.

Reviewed on Feb 27, 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

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

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

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
$72 nightly
The price is $87 total per night from Mar 12 to Mar 13
$87 total
Mar 12 - Mar 13
Total with taxes and fees
8/10 Very Good! (2,527 reviews)
We stayed in a suite and it was very clean & spacious. Front desk staff were very courteous and friendly. Would go back.

Reviewed on Feb 27, 2026

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
$58 nightly
The price is $69 total per night from Mar 15 to Mar 16
$69 total
Mar 15 - Mar 16
Total with taxes and fees
7.8/10 Good! (2,051 reviews)
Everything was as I expected. Clean quiet and staff were friendly and helpful

Reviewed on Feb 28, 2026

Travelodge by Wyndham Barrie
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
$60 nightly
The price is $71 total per night from Mar 15 to Mar 16
$71 total
Mar 15 - Mar 16
Total with taxes and fees
7/10 Good! (1,262 reviews)
Courteous staff

Reviewed on Feb 27, 2026

Days Inn by Wyndham Barrie
See all 569 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 $379 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.