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.
Night Hotel Broadway
Manhattan
CA $1,304
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,693 reviews)
AWFUL beds, awful pillows. The mattress was lumpy, the pillows were lumpy and thin, felt like they were filled with bits of trash. The interior of the rooms are extremely dated and worn down, looks more like a motel on the side of the road in the middle of nowhere than a three star hotel. Typical in NYC because they know they'll still make money. For the amount of money for a night, just embarrassing.
Reviewed on Sep 29, 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 $160
CA $184 total
Oct 4 - Oct 5
includes taxes & fees
8/10 Very good! (1,468 reviews)
"Perfect location for us and right near highway."
Reviewed on Sep 28, 2026
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
CA $137
CA $159 total
Oct 21 - Oct 22
includes taxes & fees
7.6/10 Good! (594 reviews)
"The room was decent. Clean and comfortable bed. Quiet. Rusty, leaning floor lamp in corner of bedroom. Decent value. The bathroom was not in great condition. Damaged ceiling tile over the shower from second floor. Empty shampoo conditioner mounted on shower wall. Very sparce continental ..."
Reviewed on Sep 29, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $156
CA $181 total
Oct 21 - Oct 22
includes taxes & fees
9/10 Wonderful! (1,089 reviews)
"Staff was very helpful..Room was clean and spacious..amenities great and good breakfast.bar was a plus"
Reviewed on Sep 28, 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
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 during your stay in Wingdale.
Pawling Nature Reserve
You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
Frequently asked questions
How much does a Wingdale vacation package cost?
Offering great value package deals from CA $1,304 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.
