Hillsdale Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Hillsdale Vacation
History, cuisine, art and more … There's a whole lot to discover with a Hillsdale vacation package. And with the ability to customize your city break, it's guaranteed to be one that's memorable. Any trip to Hillsdale has to include a little sightseeing. Elmvale Jungle Zoo is a great place to start your exploring. Expedia can help you escape your daily routine. Tailor your vacation to Hillsdale to suit your style of travel, whatever that may be.
Top Hillsdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Windermere House
CA $1,088
per person
Oct 14 - Oct 17
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Muskoka (YQA)
9.2/10 Wonderful! (1,019 reviews)
Everything was perfect.
The only complaint was the pressure of the shower in room 309 was way to weak. Needs to be fixed.
Reviewed on Aug 30, 2026
Ready to book your vacation to Hillsdale?
Hillsdale Hotel Deals
Monte Carlo Inn Barrie Suites
81 Hart Dr Barrie ON
Fully refundableReserve now, pay when you stay
CA $95
CA $114 total
Oct 1 - Oct 2
includes taxes & fees
Carriage Ridge Resort, an Ascend Collection Resort
3303 Line 3 N Oro-Medonte ON
Fully refundable
CA $114
CA $133 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,021 reviews)
"Loved having a full kichen, private balcony & outdoor new BBQ'S"
Reviewed on Aug 31, 2026
Residence & Conference Centre - Barrie
One Georgian Drive Barrie ON
7.4/10 Good! (883 reviews)
"The room and bathroom was clean and comfortable. The stafff are friendly and efficient. Slept well and left in the a,m."
Reviewed on Sep 1, 2026
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.
What to do in Hillsdale
Smartphone Audio Driving Tour between Wasaga Beach and Toronto
CA $8
per traveller
Frequently asked questions
How much does a Hillsdale vacation package cost?
Offering excellent value package deals from CA $689 on Expedia, you'll be thrilled with how little a vacation to Hillsdale costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Hillsdale?
You're likely to find reduced prices and greater availability in January, February and April. Take a look at our cheap Hillsdale vacation packages and you could get some great off-season discounts.
How many days is enough for Hillsdale?
The ideal duration of your Hillsdale vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to hit all the major attractions and discover some hidden treasures along the way.
How to find the best Hillsdale package deals?
Landing a cheap Hillsdale package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Hillsdale package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Hillsdale vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can tailor your Hillsdale escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
How to plan a trip to Hillsdale?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Hillsdale.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and flights. Your accommodations will probably be the largest expense during your trip to Hillsdale.
- Decide how long to go away for: Now that you're more familiar with Hillsdale, you can figure out the ideal length of your vacation. Pull together a draft plan and allocate enough time to cover everything you want to see.
- Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the right Hillsdale vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
