Oak Point Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Oak Point vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 13 - Jan 16

    Canad Inns Destination Centre Transcona + Flight

    Transcona
    3 nights
    3.0 star property
    8.4/10 - Very good (1,000 reviews)
    "The staff are very professional. Room was very clean. Food was good. Our checkin was for 4 o'clock but we waited just over an hour to get checked in because room wasn't ready. That was a bit of a drag. Everything else was awesome. Great pool and waterside."
    Reviewed November 4, 2026
    Roundtrip • Edmonton (YEG) - Winnipeg (YWG)
    YEG - YWG • Nonstop YWG - YEG • Nonstop
    CA $675
    CA $519
    per traveller
    found 1 day ago
    Canad Inns Destination Centre Transcona
  • Jan 13 - Jan 16

    Sandman Hotel & Suites Winnipeg Airport + Flight

    St. James
    3 nights
    3.0 star property
    8.2/10 - Very good (1,771 reviews)
    Roundtrip • Edmonton (YEG) - Winnipeg (YWG)
    YEG - YWG • Nonstop YWG - YEG • Nonstop
    CA $821
    CA $614
    per traveller
    found 1 day ago
    Sandman Hotel & Suites Winnipeg Airport
  • Jan 13 - Jan 16

    Humphry Inn & Suites + Flight

    Downtown Winnipeg
    3 nights
    2.5 star property
    8.4/10 - Very good (1,770 reviews)
    "The Humphry Inn is located within walking distance of Union station and the VIA rail. The complementary breakfast is cereal, breads and a few hot items. The room was very quiet and faced the parking lot. I would stay at the Humphrey Inn again!"
    Reviewed November 6, 2026
    Roundtrip • Edmonton (YEG) - Winnipeg (YWG)
    YEG - YWG • Nonstop YWG - YEG • Nonstop
    CA $733
    CA $571
    per traveller
    found 1 day ago
    Humphry Inn & Suites
  • Jan 13 - Jan 16

    Victoria Inn Hotel and Convention Centre Winnipeg + Flight

    St. James
    3 nights
    3.0 star property
    8.4/10 - Very good (3,335 reviews)
    Roundtrip • Edmonton (YEG) - Winnipeg (YWG)
    YEG - YWG • Nonstop YWG - YEG • Nonstop
    CA $661
    CA $544
    per traveller
    found 1 day ago
    Victoria Inn Hotel and Convention Centre Winnipeg
  • Jan 13 - Jan 16

    Canad Inns Destination Centre Polo Park + Flight

    Polo Park
    3 nights
    3.0 star property
    8.0/10 - Very good (1,010 reviews)
    "Nice clean rooms , food poisoning from the restaurant though"
    Reviewed November 6, 2026
    Roundtrip • Edmonton (YEG) - Winnipeg (YWG)
    YEG - YWG • Nonstop YWG - YEG • Nonstop
    CA $736
    CA $610
    per traveller
    found 1 day ago
    Canad Inns Destination Centre Polo Park

Frequently Asked Questions

How much does an Oak Point vacation package cost?

You'll find cheap prices from CA $519 on Expedia for your Oak Point getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oak Point costs.

What are the cheapest months to go to Oak Point?

If you're hoping to score a cheap Oak Point vacation package, consider visiting in January, February and November. You're likely to find lower rates on flights and accommodations during these months — perfect for budget-conscious travellers.

How many days is enough for Oak Point?

The ideal duration for your Oak Point vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to go to all the main attractions and discover some hidden treasures along the way.

How to find the best Oak Point package deals?

Use Expedia's filters to find some of the best Oak Point package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Oak Point package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book an Oak Point vacation as a package?

An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can personalize your Oak Point getaway to match your exact style. Choose 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 Oak Point?

Land incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Oak Point getaway.

How to plan a trip to Oak Point?

  1. Choose your dates: What you want to do in Oak Point and your preferred season can help you decide when to go.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Oak Point. Then, select a hotel that matches your budget, whether that's a low-cost option or a swankier retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Oak Point. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find an Oak Point 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.