Woodbury Vacations from $607
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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!
The Latest Woodbury vacation packages
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
$1,150
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
33 Hotel, New York City, Seaport
Manhattan
$1,374
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,005 reviews)
When checking in the front desk informed me that I had $42 to spend in room order including patronage at the restaurant on site. They did not mention that the spend doesn’t include or cannot apply to gratuity. I spent $40 on the entire bill at the restaurant and the hotel only took off the portion without the gratuity. The toilet was not flushing well and toward the end of my stay the water never stopped running so I had to call the front desk at 10pm. The elevator was not working but the technician appeared to not communicate to hotel guests by just standing there. I had to carry 3 bags and took a few steps down to another elevator.
Reviewed on Aug 11, 2026
Stay near popular Woodbury attractions
Woodbury Common Premium Outlets
8.8/10 (1,317 reviews)
You can find the perfect gifts to bring home with a trip to Woodbury Common Premium Outlets, a favorite shopping spot in Woodbury. While you're in the area, stroll along the lakeside.
Lake Tiorati Beach
If a restful vacation is part of your travel plans, Lake Tiorati Beach might be the perfect place to seek out during your trip to Woodbury. While you're in the area, find time to visit its shops.
Old Glory Mall Shopping Center
During your trip to Woodbury, you can search for that perfect souvenir at Old Glory Mall Shopping Center. While you're in the area, stroll along the riverfront.
Palaia Vineyards Winery
You can enjoy a tasting or tour at Palaia Vineyards Winery during your travels to Woodbury. Discover the mountain views and shops in this family-friendly area.
What to do in Woodbury
Guided Shared Group Forest Bathing Session in Serene Woodland Park
$55
per adult
Woodbury Hotel Deals
Hampton Inn Harriman Woodbury
60 Centre Dr Central Valley NY
Fully refundableReserve now, pay when you stay
$122 nightly
$150 total
Sep 1 - Sep 2
Total with taxes and fees
Comfort Suites Central Valley - Woodbury
100 Estrada Road Central Valley NY
Fully refundable
$110 nightly
$136 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (115 reviews)
"The location was convenient for Woodbury commons outlet but the cleanliness of the bathroom, specifically the bathtub left a lot to be desired also the lobby and elevator floors were very dirty"
Reviewed on Aug 13, 2026
Americas Best Value Inn at Central Valley-Woodbury
139 Route 32 Central Valley NY
Fully refundableReserve now, pay when you stay
$99 nightly
$122 total
Aug 16 - Aug 17
Total with taxes and fees
7.2/10 Good! (1,008 reviews)
"Room was clean. Beds clean."
Reviewed on Aug 11, 2026
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.
Find the Best Woodbury Vacation Packages
Woodbury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Westchester County Airport (HPN) |
Population | 10,900 |
Top Sights | Brotherhood Winery, Castle Fun Center and Palaia Vineyards Winery |
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Frequently asked questions
How much does a Woodbury vacation package cost?
You'll find cheap prices from $607 on Expedia for your Woodbury getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Woodbury costs.
What are the cheapest months to go to Woodbury?
You're likely to find lower rates and better availability in December, January and February. Browse our cheap Woodbury vacation packages and you could score some excellent off-season deals.
How many days is enough for Woodbury?
Generally, a handful of days is enough to visit the top attractions during your Woodbury vacation. However, if you prefer to have more time to chill out or take day trips, consider extending your itinerary.
How to find the best Woodbury package deals?
Finding a cheap Woodbury package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Woodbury package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Woodbury vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Woodbury getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Woodbury?
If you've got your Woodbury travel dates locked in, book as soon as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Woodbury?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Woodbury.
- Set a budget: Factor in costs like food, flights and transportation when calculating how much to save for your trip to Woodbury. Then, pick a property that fits your budget, whether that's a low-cost stay or a deluxe getaway.
- Use our trip planning tool to explore Woodbury: Research every part of your trip to Woodbury with this comprehensive planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings.
- Decide how many days away: Start by compiling a list of the attractions you want to get to in Woodbury. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Woodbury vacation package that brings all your bookings together.
- Book any excursions or activities: Now to the fun part — locking in everything you want to do and see. Browse some of the best things to do in Woodbury and reserve your tickets in advance to save time (and maybe some spending money too!).
Does Expedia offer Book Now, Pay Later Woodbury vacation packages?
Your Woodbury break should be a relaxing escape from your busy life, not a reason for money worries. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
