Wingdale Vacations from $339

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The Latest Wingdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Topping Rose House

Topping Rose House

4.5 out of 5
Price was $735, price is now $339 per person
$339
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,375, price is now $1,783 per person
$1,783
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10

Reviewed on Jan 29, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $2,726, price is now $1,502 per person
$1,502
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby.

Reviewed on Feb 2, 2026

Mountain Springs Lake Resort

Mountain Springs Lake Resort

3.5 out of 5
Price was $727, price is now $403 per person
$403
per person
Mar 15 - Mar 19
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (234 reviews)
The staff was friendly and helpful. They were great!

Reviewed on Feb 2, 2026

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Wingdale Hotel Deals

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Feb 16 to Feb 17
$107 total
Feb 16 - Feb 17
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Clean and good staff

Reviewed on Jan 27, 2026

Courtyard by Marriott Poughkeepsie
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $80 total per night from Feb 9 to Feb 10
$80 total
Feb 9 - Feb 10
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
Clean rooms, hotel could use some updates.

Reviewed on Jan 18, 2026

Best Western Danbury/Bethel
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $174 total per night from Feb 9 to Feb 10
$174 total
Feb 9 - Feb 10
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Excellent all around. Despite several birthday parties and a wedding in the restaurant the room was very quiet.

Reviewed on Feb 2, 2026

Hotel Zero Degrees Danbury
See all 835 properties in Wingdale
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 $339 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.