Wingdale Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Wingdale
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
€2,321
per person
5 Dec - 10 Dec
found 1 day ago
Return flight included
Athens (ATH) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
We were expecting a much better room. The room seems outdated, the bedding was really uncomfortable and not cozy. Pillows were uncomfortable and we have to ask for more pillows. The sofa bed where my son slept, was dirty and we had to ask for additional clean sheets and blankets.
The hallways looked like a hospital and just felt not cozy at all.
The staff is amazing and very friendly.
Reviewed on 23 Oct 2026
Ink 48 Hotel
Manhattan
€2,018
per person
5 Dec - 10 Dec
found 1 day ago
Return flight included
Athens (ATH) to New York (JFK)
8.4/10 Very good! (1,813 reviews)
Old and out of date. Drained carpet and stained furniture in the room. AC barely worked. Pictures online don’t match at all what the rooms look like.
Reviewed on 24 Oct 2026
NobleDEN Hotel
Manhattan
€1,907
per person
28 Dec - 3 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (1,661 reviews)
The draft was welcoming , friendly and knowledgeable. They suggested places to try and easy ways to get around the city.
The rooms were clean and our view was great!
The rooftop was especially nice, with ample seating and a 360° view of the entire city.
Complimentary coffee, tea and morning croissants was a nice touch.
Morgan at the front desk was a fountain of information!
We would definitely recommend the Noble DEN for your stay!
Reviewed on 21 Oct 2026
Top hotels in Wingdale
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
€119
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (1,517 reviews)
"Nice hotel"
Reviewed on 24 Oct 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
€105
11 Nov - 12 Nov
includes taxes & fees
Heritage Hotel, Golf & Conference Center
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
€132
3 Nov - 4 Nov
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"A great place for a one-night stop."
Reviewed on 24 Oct 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.
Stay near popular Wingdale attractions
Pawling Nature Reserve
You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
Leather Hill Preserve
You can take time to visit Leather Hill Preserve 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 as part of your travels around Wingdale.
Frequently asked questions
How much does a Wingdale holiday package cost?
Offering excellent value package deals from €1,309 on Expedia, you'll be surprised at how little a holiday to Wingdale costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Wingdale?
January, February and March are the best times to search for cheap Wingdale holiday packages. Choosing to travel in quieter periods means you can usually find lower prices on hotels and flights.
How many days is enough for Wingdale?
The ideal length for your Wingdale holiday depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to check out all the major sights and explore some hidden spots 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 holiday package as early as possible.
Is it cheaper to book a Wingdale holiday as a package?
Expedia holiday 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 holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Wingdale?
If you've got your Wingdale holiday 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.
How to plan a trip to Wingdale?
- Pick your dates: What you want to do in Wingdale and your preferred season will help you decide when to get away.
- Plan your budget wisely: Besides the cost of your accommodation, you should consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Wingdale.
- Decide how long to go away for: Now that you're up to speed on Wingdale, you can figure out the perfect length of your holiday. Pull together a rough plan and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Wingdale holiday 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.
