Hillsdale Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 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
Hillsdale Holiday
Our pick of the best Hillsdale Hotel Deals
Monte Carlo Inn Barrie Suites
81 Hart Dr Barrie ON
Fully refundableReserve now, pay when you stay
NZ$140
1 Oct - 2 Oct
includes taxes & fees
8/10 Very good! (2,950 reviews)
"Our room was clean. The water in the tub was running very brown (once we ran it for several minutes it resolved.) The provided breakfast was very basic, you could pay roughly 8$ to have eggs etc.."
Reviewed on 31 Aug 2026
Carriage Ridge Resort, an Ascend Collection Resort
3303 Line 3 N Oro-Medonte ON
Fully refundableReserve now, pay when you stay
NZ$161
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,021 reviews)
"Loved having a full kichen, private balcony & outdoor new BBQ'S"
Reviewed on 31 Aug 2026
Residence & Conference Centre - Barrie
One Georgian Drive Barrie ON
7.4/10 Good! (882 reviews)
"The room was clean. The staff was very helpful"
Reviewed on 31 Aug 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
NZ$10
per traveller
Frequently asked questions
How much does a Hillsdale holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Hillsdale costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Hillsdale?
You're likely to find reduced prices and greater availability in January, February and April. Browse our cheap Hillsdale holiday packages and you could land some excellent off-season deals.
How many days is enough for Hillsdale?
With a well-organised itinerary, you can easily hit the main Hillsdale sights in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your Hillsdale holiday for longer.
How to find the best Hillsdale package deals?
Start your search for a Hillsdale package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Hillsdale package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillsdale adventure off to a flying start.
Is it cheaper to book a Hillsdale holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Hillsdale getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Hillsdale?
Enjoy incredible discounts by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Hillsdale escape.
How to plan a trip to Hillsdale?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Hillsdale.
- Set your budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Hillsdale. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a more luxurious retreat.
- Work out your trip length: Think about how long you want to spend discovering Hillsdale. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
- Combine your airfare and accommodation: After you've settled on your dates and duration, book the right Hillsdale holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
