Wingdale Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Wingdale Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Library Hotel by Library Hotel Collection
Manhattan
S$1,623
per person
2 Oct - 3 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.6/10 Exceptional! (1,005 reviews)
Hotel is a little worn. There was ongoing construction on my floor. Minor detail but the remote control for my tv didn’t work.
The complimentary breakfast is pretty slim, basically just coffee and croissants.
Reviewed on 22 Aug, 2026
Top hotels in Wingdale
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
S$156
20 Sept - 21 Sept
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
S$149
8 Sept - 9 Sept
includes taxes & fees
9/10 Wonderful! (1,041 reviews)
"👍"
Reviewed on 28 Aug, 2026
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
S$145
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Clean room; helpful staff and good location. Very accesible to our destinations"
Reviewed on 27 Aug, 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 S$1,623 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
