A cityscape with a mix of historic and modern buildings, a parking lot, and a river in the background.

Orangeville Vacations from $531

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Your Orangeville Vacation

When an adventure in the city is calling, answer it with a vacation package to Orangeville. With all your travel plans worked out before you go, all you have to do here is concentrate on having fun. A trip to Orangeville is a wonderful opportunity to take in the sights. Make sure you visit popular attractions like Hockley Valley Resort, Theatre Orangeville and Island Lake Conservation Area. Don't delay visiting this city any longer. Your dream Orangeville vacation is just a few clicks away with Expedia.

The Latest Orangeville Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern interior with a central fireplace, a dining area with a chair and table, and a hallway with an elevator.
    Jan 29 - Feb 1

    Union Hotel + Flight

    Downtown Toronto
    3 nights
    4.0 star property
    9.2/10 - Wonderful (2,881 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YTZ • Nonstop YTZ - BOS • 1 stop
    $720
    $531
    per traveler
    found 1 day ago
    Union Hotel
  • A modern hotel with a prominent corner entrance, large windows, and a visible street view.
    Dec 23 - Dec 28

    Hotel Riu Plaza Toronto + Flight

    Downtown Toronto
    5 nights
    4.0 star property
    9.4/10 - Exceptional (5,277 reviews)
    "Great location. Room was spacious and breakfast was a nice variety and good."
    Reviewed November 11, 2026
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YYZ • Nonstop YYZ - BOS • Nonstop
    $1,221
    $821
    per traveler
    found 1 day ago
    Hotel Riu Plaza Toronto
  • A modern kitchen with wooden stools, a dining area with a white sofa, and a large window providing a view of the city.
    Jan 14 - Jan 17

    1 Hotel Toronto + Flight

    Downtown Toronto
    3 nights
    5.0 star property
    9.6/10 - Exceptional (867 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YYZ • Nonstop YYZ - BOS • Nonstop
    Save 100% on your flight
    $1,290
    $894
    per traveler
    found 1 day ago
    1 Hotel Toronto
  • A hotel room with a bed, a sofa, a dining table with chairs, and a brick wall.
    Dec 29 - Jan 3

    Cabbagetown Inn + Flight

    Downtown Toronto
    5 nights
    3.0 star property
    8.6/10 - Excellent (109 reviews)
    "Clean, good location friendly staff"
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YYZ • Nonstop YYZ - BOS • Nonstop
    $903
    $662
    per traveler
    found 1 day ago
    Cabbagetown Inn
  • A modern hotel with a glass facade, a visible restaurant area, and a sign indicating it is located in Toronto.
    Dec 23 - Dec 28

    Shangri-La Toronto + Flight

    Downtown Toronto
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,427 reviews)
    Roundtrip • Boston (BOS) - Toronto (YYZ)
    BOS - YYZ • Nonstop YYZ - BOS • Nonstop
    $1,640
    $1,230
    per traveler
    found 1 day ago
    Shangri-La Toronto

Where to stay near Orangeville

Discover the charm of Orangeville, ON, perfect for family travel and outdoor adventures. Explore downtown Orangeville for local shops and eateries, or use an online map to find nearby parks and recreational spots. Plan your next trip to enjoy friendly vibes and eco-friendly experiences!
A wooden staircase leading up a rocky path surrounded by trees.

Mono

Discover Mono, a welcoming destination perfectly suited for families and adventure seekers looking for a memorable trip. This charming city offers access to outdoor activities like skiing at Hockley Valley Provincial Park, exploration at Island Lake Conservation Area, and relaxation by the shores of Sharon Lake. Just about a 6-mile drive from Orangeville, Mono makes it easy to unwind while being close to nature. Choosing Mono for your stay ensures a delightful mix of adventure and comfort.

Alton

Experience the charm of Alton, an excellent hub for adventure travelers and families eager to explore the great outdoors. With attractions like the Alton Mill Arts Centre, the Island Lake Conservation Area, and the Hillsburgh Library nearby, visitors can immerse themselves in nature, art, and local culture. Located about 5 miles by car from Orangeville, Alton offers a smart choice for those seeking a memorable getaway without seasonal constraints.

A field of corn with trees in autumn colors.
Photo by Chantal's Photos
Open Photo by Chantal's Photos

Mono Mills

If you are a nature-loving family or an adventure seeker, look no further than Mono Mills, which features stunning outdoor experiences and activities. Explore the scenic beauty of Hockley Valley Provincial Park, enjoy the tranquility of Glen Haffy Conservation Area, or relax at Victoria Park. Located about 7 miles by car from Orangeville, Mono Mills offers easy access to these attractions, making it a smart choice for your vacation stay.

A terraced landscape with reddish soil, surrounded by green vegetation and trees.

Caledon

Immerse yourself in Caledon, where adventure seekers and families can easily access a wealth of outdoor experiences. This vibrant city offers attractions like the breathtaking Belfountain Conservation Area, perfect for nature lovers, and the Alton Mill Arts Centre, ideal for those who appreciate local art. With popular venues for golf and skiing, Caledon makes for a delightful weekend getaway. It’s about a 12-mile drive from Orangeville, making it a smart choice for your next hotel booking.

A speedboat with a checkered pattern and the text "BASE THIS PACH" on its side, moving through a marina with other boats docked in the background.
Photo by Ontario's Southwest
Open Photo by Ontario's Southwest

Amaranth

Travelers visiting the area often choose Amaranth, especially families and nature enthusiasts seeking close proximity to stunning outdoor experiences. With attractions like the Island Lake Conservation Area and Hockley Valley Provincial Park, visitors can enjoy hiking, skiing, and golfing in beautiful surroundings. Amaranth is about an 8-mile drive from Orangeville, making it easy to access and explore. This charming city offers budget-friendly accommodations, making it a smart choice for your getaway.

Discover the most popular places to visit in Orangeville

Island Lake Conservation Area

8.8/10 (16 reviews)
Explore the great outdoors at Island Lake Conservation Area, a lovely green space in Orangeville. You can seek out the hiking trails while in the area.
See properties

Orangeville Hotel Deals

A spacious lobby with a central staircase, a reception desk, and a modern chandelier.

Best Western Plus Orangeville Inn & Suites

Best Western Plus Orangeville Inn & Suites
2.5 star property
0.7 mi from Orangeville
8.8 out of 10, Excellent, (1,000 reviews)
"Clean, convenient, spacious room, good breakfast."
$149 nightly
The price is $168
Nov 12 - Nov 13
Total with taxes and fees
Best Western Plus Orangeville Inn & Suites
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 Orangeville

Frequently Asked Questions

How much does an Orangeville vacation package cost?

Offering excellent value package deals from $531 on Expedia, you'll be surprised at how little a vacation to Orangeville costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Orangeville?

August, September and December are great times to search for cheap Orangeville vacation packages. Traveling in less busy months means you can usually find better prices on hotels and flights.

How many days is enough for Orangeville?

Usually, a handful of days is enough to go to the main attractions during your Orangeville vacation. But if you want to have some time to chill out or take day tours, think about extending your itinerary.

Is it worth booking a vacation package to Orangeville?

Orangeville offers everything you need for an amazing escape. Begin your Orangeville vacation on a high note by exploring major attractions like Island Lake Conservation Area.

How to find the best Orangeville package deals?

Start your search for an Orangeville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Orangeville package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Orangeville escape off to a flying start.

Is it cheaper to book an Orangeville vacation as a package?

You can enjoy significant savings on your Orangeville retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Orangeville?

If you've got your Orangeville vacation dates locked in, book as early as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.

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

If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Orangeville vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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