Wingdale Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 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 hotels in Wingdale
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
Rp2.203.136
Rp2.533.607 total
20 Sept - 21 Sept
includes taxes & fees
8/10 Very good! (1,435 reviews)
"Left me the wrong clicker for tv so I had to call for a new one. Dirty rugs. Should be cleaned"
Reviewed on 12 Sept 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
Rp1.778.711
Rp2.065.529 total
22 Sept - 23 Sept
includes taxes & fees
9/10 Wonderful! (1,066 reviews)
"Very nice property. Only downside is that you cannot walk anywhere. There are no sidewalks on the main road."
Reviewed on 13 Sept 2026
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
Rp1.571.606
Rp1.760.198 total
20 Sept - 21 Sept
includes taxes & 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.
Stay near popular Wingdale attractions
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.
Leather Hill Preserve
You can take time to visit Leather Hill Preserve during your travels to 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 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.
