Wingdale Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Wingdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
CA $1,322
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
Ready to book your vacation to Wingdale?
Wingdale Hotel Deals
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
CA $134
CA $154 total
Aug 16 - Aug 17
includes taxes & fees
8/10 Very good! (1,390 reviews)
"Very clean and the staff was excellent."
Reviewed on Aug 13, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $153
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
CA $132
CA $154 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"I reserved two rooms. When I returned to my room in the evening I noticed mold on the room and water on the floor. We notified the front desk but they refused to help or even address the matter. We were very disappointed, they didnt even offer to come up and see the room."
Reviewed on Aug 13, 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
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.
Pawling Nature Reserve
You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
Olivet University
Walk around the campus at Olivet University during your stay in Wingdale.
Frequently asked questions
How much does a Wingdale vacation package cost?
Offering great value package deals from CA $1,290 on Expedia, you'll be thrilled with how little a vacation to Wingdale costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Wingdale?
You can generally find lower rates and better availability in January, February and March. Browse our cheap Wingdale vacation packages and you could get some excellent off-season deals.
How many days is enough for Wingdale?
Usually, a handful of days is enough to go to the top sights during your Wingdale vacation. However, if you want to have some time to relax or take day tours, consider extending your itinerary.
How to find the best Wingdale package deals?
Finding a cheap Wingdale package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Wingdale package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Wingdale vacation as a package?
You can enjoy significant savings on your next Wingdale break by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Wingdale?
If you're considering a spur-of-the-moment Wingdale vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Wingdale?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Wingdale.
- Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your accommodations will likely be the biggest expense during your trip to Wingdale.
- Determine how many days away: Start by making a list of all the activities and sights you want to get to in Wingdale. Then, estimate how long you'll need for each, along with any travel time.
- Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the right Wingdale vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
