A tranquil lakeside scene at sunset with a wooden pavilion on stilts and a calm water surface reflecting the sky.

Cumberland Beach Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Cumberland Beach Vacation

The adventure-packed city of Cumberland Beach is calling. Discover all its secrets with a Cumberland Beach vacation package that's custom made for you. If sightseeing is a priority during your trip to Cumberland Beach, make sure you stop by leading attractions like Hawk Ridge Golf and Country Club and Orillia Square Mall. Expedia has what you need to escape the everyday. Tailor your vacation to Cumberland Beach to match your travel style, whatever that may look like.

Top Cumberland Beach vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A cozy interior with a stone fireplace, leather sofas, and large windows offering a view of the outdoors.
    Jan 15 - Jan 17

    Jolly Roger Inn & Resort + Flight

    Seguin
    2 nights
    3.5 star property
    7.8/10 - Good (866 reviews)
    "I love these place"
    Reviewed November 11, 2026
    Roundtrip • Halifax (YHZ) - Muskoka District (YQA)
    YHZ - YQA • 2 stops YQA - YHZ • 1 stop
    CA $642
    CA $598
    per traveller
    found 23 hours ago
    Jolly Roger Inn & Resort
  • A wooden dock extending into calm water with two blue chairs and umbrellas on each side.
    Dec 23 - Dec 28

    Haliburton Post House + Flight

    Minden
    5 nights
    4.0 star property
    10/10 - Exceptional (11 reviews)
    Roundtrip • Fredericton (YFC) - Muskoka District (YQA)
    YFC - YTZ • Nonstop YTZ - YFC • 1 stop
    CA $1,310
    CA $1,008
    per traveller
    found 8 hours ago
    Haliburton Post House
  • An outdoor seating area with chairs arranged around a fire pit, string lights overhead, and a building in the background.
    Jan 15 - Jan 17

    Sunnylea Resort + Flight

    Georgian Bay
    2 nights
    2.5 star property
    8.4/10 - Very good (123 reviews)
    Roundtrip • Halifax (YHZ) - Muskoka District (YQA)
    YHZ - YQA • 2 stops YQA - YHZ • 1 stop
    CA $754
    CA $704
    per traveller
    found 1 day ago
    Sunnylea Resort
  • A hotel room with a large bed, a bench, a bedside table, a nightstand, a mirror, and a window with a view of greenery.
    Jan 15 - Jan 17

    The Dudley Inn + Flight

    Muskoka Lakes
    2 nights
    2.5 star property
    9.8/10 - Exceptional (120 reviews)
    Roundtrip • Halifax (YHZ) - Muskoka District (YQA)
    YHZ - YQA • 2 stops YQA - YHZ • 1 stop
    CA $739
    CA $694
    per traveller
    found 1 day ago
    The Dudley Inn
  • A hotel with a distinctive architectural style, featuring large wooden barrel-shaped structures, a white exterior, and a red roof.
    Jan 15 - Jan 17

    Windermere House + Flight

    Muskoka Lakes
    2 nights
    3.5 star property
    9.4/10 - Exceptional (1,009 reviews)
    "Wonderful helpful staff clean room comfortable bed. Our room was large and bright albeit drab no art and all grey. We loved the hot tub and sauna. We have stayed at the JW Marriot down the street and Windermere House was 1/3 the price and Windermere is a MUCH BETTER HOTEL!!!"
    Reviewed November 10, 2026
    Roundtrip • Halifax (YHZ) - Muskoka District (YQA)
    YHZ - YQA • 2 stops YQA - YHZ • 1 stop
    CA $768
    CA $725
    per traveller
    found 23 hours ago
    Windermere House

Cumberland Beach Hotel Deals

A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a sun umbrella.

Days Inn by Wyndham Orillia

Days Inn by Wyndham Orillia
2.5 star property
7.4 km from Cumberland Beach
8.8 out of 10, Excellent, (1,892 reviews)
The price is CA $128
CA $145 total
includes taxes & fees
Nov 17 - Nov 18
Days Inn by Wyndham Orillia
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 Cumberland Beach

Frequently Asked Questions

How much does a Cumberland Beach vacation package cost?

You can pick up a vacation package to this popular destination from CA $598 on Expedia. But how much your vacation to Cumberland Beach costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Cumberland Beach?

January, February and March are great times to search for cheap Cumberland Beach vacation packages. Travelling in quieter months means you can typically find reduced prices on flights and accommodations.

How many days is enough for Cumberland Beach?

Usually, a handful of days is enough to explore the major sights during your Cumberland Beach vacation. However, if you want to have more time to rest or go on day trips, think about extending your trip.

How to find the best Cumberland Beach package deals?

Use Expedia's filter tool to help you find some of the best Cumberland Beach package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Cumberland Beach package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.

Is it cheaper to book a Cumberland Beach vacation as a package?

Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Cumberland Beach vacation by choosing your favourite airline, accommodation type and car class.

When to book a vacation package to Cumberland Beach?

Score amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Cumberland Beach trip.

How to plan a trip to Cumberland Beach?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Cumberland Beach.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your hotel will probably be the largest expense during your trip to Cumberland Beach.
  3. Work out your trip length: Think about how much time you want to spend discovering Cumberland Beach. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Cumberland Beach vacation package that brings all your bookings together.

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