Hillsdale Vacations from $462

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    • 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.

    The Latest Hillsdale Vacation Packages

    Price found within the past 48 hours. Click for updated prices.

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    What to do in Hillsdale

    Toronto–Wasaga Beach Self-Guided Smartphone Audio Driving Tour

    Toronto–Wasaga Beach Self-Guided Smartphone Audio Driving Tour

    $6

    per traveler

    0% of travelers recommend

    See all activities in Hillsdale

    Hillsdale Hotel Deals

    Carriage Ridge Resort, an Ascend Collection Resort

    A patio with stone seating and a fire pit, surrounded by a stone wall and greenery.
    • Address: 3303 Line 3 N, Oro-Medonte, ON, L0L 2L0, CA
    • Location: 4.8 mi from Hillsdale
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 1071 reviews)
    • Price: $83 nightly, $94 total, Nov 22 - Nov 23, Total with taxes and fees
    • Review: Clean

    Travelodge by Wyndham Barrie

    Breakfast area
    • Address: 300 Bayfield St, Barrie, ON, L4M3B9, CA
    • Location: 12.8 mi from Hillsdale
    • Star rating: 2/5
    • Guest rating: 7.8/10 (Good, 2347 reviews)
    • Price: $57 nightly, $68 total, Dec 1 - Dec 2, Total with taxes and fees
    • Review: It was okay, the room was clean and its walking distance to a few places to eat

    Fairfield Inn & Suites by Marriott Orillia

    A modern dining area with a long counter, blue chairs, and pendant lighting.
    • Address: 8 MULCAHY COURT, Orillia, ON, L3V 8B3, CA
    • Location: 15.3 mi from Hillsdale
    • Star rating: 3/5
    • Guest rating: 9.8/10 (Exceptional, 968 reviews)
    • Price: $95 nightly, $111 total, Dec 13 - Dec 14, Total with taxes and fees

    Best Western Plus Barrie

    A modern hotel lobby with a seating area, a kitchenette, and a view of the outdoors.
    • Address: 35 Hart Drive, Barrie, ON, L4N 5M3, CA
    • Location: 14 mi from Hillsdale
    • Star rating: 2.5/5
    • Guest rating: 8.4/10 (Very good, 1001 reviews)
    • Price: $77 nightly, $92 total, Nov 29 - Nov 30, Total with taxes and fees

    Quality Inn

    A hotel with a prominent 'Quality Inn' sign, featuring a stone facade and multiple windows.
    • Address: 75 Hart Dr, Barrie, ON, L4N5M3, CA
    • Location: 14.1 mi from Hillsdale
    • Star rating: 2.5/5
    • Guest rating: 8.2/10 (Very good, 1004 reviews)
    • Price: $61 nightly, $73 total, Dec 6 - Dec 7, Total with taxes and fees
    • Review: Breakfast could have been better..sausages were not very good, orange juice was very diluted..

    Comfort Inn Orillia

    A hotel reception area with a red wall, a wooden reception desk, and a grey counter.
    • Address: 75 Progress Dr, Orillia, ON, L3V6H1, CA
    • Location: 16.5 mi from Hillsdale
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 1001 reviews)
    • Price: $76 nightly, $89 total, Dec 13 - Dec 14, Total with taxes and fees
    • Review: Had to request housekeeping for second day. We were not advised of this . At a very early time Sunday morning noisy construction started on hotel sidewalk.

    Monte Carlo Inn Barrie Suites

    A spacious bathroom with a large bathtub, a wooden vanity, and a fireplace.
    • Address: 81 Hart Dr, Barrie, ON, L4N5M3, CA
    • Location: 14.2 mi from Hillsdale
    • Star rating: 3/5
    • Guest rating: 8/10 (Very good, 3119 reviews)
    • Price: $69 nightly, $82 total, Dec 15 - Dec 16, Total with taxes and fees
    • Review: I like Monte Carlo hotels anywhere I go but may I say that the Barrie one was fine but the one in Vaughn Ontario is much better … the Barrie site requires updating and upgrading … also may we have at least 3 bath towels and 2 coffee pods for 2 people … also … Vaughn had everything I asked for … as wine glasses … sorry for being so picky but at the present price of hotel rooms I would like ALL to have the same standards . … thank you for listening !

    Midland Inn & Suites

    A reception area with a wooden reception desk, black leather chairs, a chandelier, a staircase, and framed pictures on the walls.
    • Address: 720 Prospect Blvd, Midland, ON, L4R 4P4, CA
    • Location: 11.5 mi from Hillsdale
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 1000 reviews)
    • Price: $69 nightly, $81 total, Dec 16 - Dec 17, Total with taxes and fees
    • Review: The breakfast needs to be more fresh.

    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.

    See all properties in Hillsdale

    Frequently Asked Questions

    How much does a Hillsdale vacation package cost?

    You can grab a vacation package to this top destination from $462 on Expedia. However, how much your vacation to Hillsdale costs will depend on the length of stay, season and hotel choice.

    What are the cheapest months to go to Hillsdale?

    You can usually find lower prices and greater availability in December, January and February. Explore our cheap Hillsdale vacation packages and you could score some great off-season discounts.

    How many days is enough for Hillsdale?

    Generally, a handful of days is enough to check out the major attractions during your Hillsdale vacation. However, if you'd like to have some time to chill out or go on day trips, think about extending your itinerary.

    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 vacation as a package?

    An Expedia vacation 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 vacation 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.

    Does Expedia offer Book Now, Pay Later Hillsdale vacation packages?

    Jet off on your dream getaway to Hillsdale with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next paycheck — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snag great deals before they disappear.

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