Wingdale Vacations from $835
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The Latest Wingdale vacation packages
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
$2,227
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,013 reviews)
This was my first time to New York. I paid extra and booked the Statue of Liberty Suite to have a good view of the Statue of Liberty. I am 72 and will probably never get to New York again. We were on the 5th floor and only had a view of the tree tops. No view at all. When I asked why we didn’t have a view of the Statue of Liberty I was told that we were on the correct side to have a view but weren’t on a high enough floor to see it. I asked for a refund and was told I could get a hotel credit. Since we were leaving and only there for one night that didn’t correct the issue. I think this is a form of fraud.
Reviewed on Sep 4, 2026
Stay near popular Wingdale attractions
Leather Hill Preserve
You can take time to visit Leather Hill Preserve during your travels to Wingdale.
Pawling Nature Reserve
You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
Dover Veterans Memorial Library
After visiting Dover Veterans Memorial Library, make a plan to see the other sights and activities in Wingdale.
Olivet University
Walk around the campus at Olivet University during your stay in Wingdale.
Wingdale Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$110 nightly
$127 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
$97 nightly
$113 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
"Hotel is in good shape with a good breakfast."
Reviewed on Sep 4, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$101 nightly
$117 total
Sep 20 - Sep 21
Total with taxes and fees
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 Wingdale Vacation Packages
Wingdale Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | James Baird State Park, Stormville Airport Antique Show & Flea Market and Whaley Lake |
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Frequently asked questions
How much does a Wingdale vacation package cost?
Offering excellent value package deals from $835 on Expedia, you'll be surprised at how little a vacation to Wingdale costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Wingdale?
If you're hoping to book a cheap Wingdale vacation package, consider planning a trip in December, January and February. You'll usually find lower rates on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Wingdale?
The ideal length of your Wingdale vacation depends on what you'd like to see. Usually, a handful of days to a week will give you time to tick off all the top attractions and explore some hidden gems along the way.
How to find the best Wingdale package deals?
Use Expedia's filter tool to help you find some great Wingdale package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Wingdale package deals in the off-peak season. Switch up 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 as early as possible.
Is it cheaper to book a Wingdale vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Wingdale vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Wingdale?
If you've got your Wingdale vacation dates finalized, book early to bag some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Wingdale vacation packages?
Your Wingdale trip is meant to be a relaxing escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
