A lakeside park with autumn foliage, a wooden dock, and a picnic area.

Woodbury 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
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Your Woodbury Vacation

With every last detail organized before you go, our Woodbury vacation packages mean you can focus more on having a good time. Whether you're staying in the neighborhood of Montrose, which is great for walking, or another part of town, this interesting city offers an array of discoveries. You'll want to take in some sights during your trip to Woodbury. Don't miss popular attractions like Woodbury Common Premium Outlets, United States Military Academy and Storm King Art Center. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your Woodbury vacation plans into gear!

Top Woodbury vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Jan 20 - Jan 23

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,832
    CA $1,120
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • Jan 15 - Jan 17

    The St. Regis New York + Flight

    Manhattan
    2 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - JFK • Nonstop JFK - YYZ • 1 stop
    CA $2,682
    CA $1,531
    per traveller
    found 2 days ago
    The St. Regis New York
  • Dec 20 - Dec 24

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (567 reviews)
    "Very convenient location. Good sized rooms."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,020
    CA $1,759
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • Feb 4 - Feb 7

    Mandarin Oriental, New York + Flight

    Manhattan
    3 nights
    5.0 star property
    9.2/10 - Wonderful (677 reviews)
    "Excellent stay"
    Reviewed October 26, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $3,333
    CA $2,079
    per traveller
    found 18 hours ago
    Mandarin Oriental, New York
  • Feb 4 - Feb 7

    The Mark + Flight

    Manhattan
    3 nights
    5.0 star property
    9.6/10 - Exceptional (724 reviews)
    "Fire alarm went off three times in middle of the night and no apology or refund."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $4,235
    CA $2,650
    per traveller
    found 18 hours ago
    The Mark

Discover the most popular places to visit in Woodbury

What to do in Woodbury

Woodbury Hotel Deals

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.

Frequently Asked Questions

How much does a Woodbury vacation package cost?

You'll find cheap prices from CA $1,120 on Expedia for your Woodbury break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Woodbury costs.

What are the cheapest months to go to Woodbury?

If you'd like to snag a cheap Woodbury vacation package, consider visiting in January, February and April. You'll usually find lower rates on airfares and hotels during these months — ideal for a budget-friendly break.

How many days is enough for Woodbury?

We suggest planning a Woodbury vacation for at least 2 days. This will allow you enough time to visit popular sights including Harriman Plaza Shopping Centre and Palaia Vineyards Winery, and explore neighbourhoods like South Blooming Grove and Beaverdam Lake-Salisbury Mills. You might even be able to squeeze in a day trip beyond Woodbury.

How to find the best Woodbury package deals?

Start your search for a Woodbury package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Woodbury package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Woodbury escape off to a flying start.

Is it cheaper to book a Woodbury vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations separately. Better still, you can personalize your Woodbury escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.

When to book a vacation package to Woodbury?

If you have your Woodbury vacation dates confirmed, book early to grab some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.

How to plan a trip to Woodbury?

  1. Pick your dates: The things you'd like to do in Woodbury and your favourite season will help you decide when to get away.
  2. Budget wisely: In addition to the cost of your hotel, you should factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to Woodbury.
  3. Decide how many days away: Start by making a list of all the attractions and activities you want to get to in Woodbury. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: Once you've nailed down your travel dates and duration, book the perfect Woodbury vacation package for you.

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