Wingdale Vacation Packages

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Top Wingdale Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 20 - Oct 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Right across from the subway entrance, a Starbucks, and next to a Walgreens. Down the street, McD’s, Subway, Panda, CVS. Blocks away from Rockefeller Center. A block away from police and fire, felt safe the whole time. The property was modern and clean. We used the microwave in the lobby, our room had a fridge. Normal room size and not NY size, bed was comfortable and room was quiet! Definitely want to stay here again on the next trip.

Reviewed on Aug. 3, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,897 reviews)
Great location - courteous staff.

Reviewed on Aug. 1, 2025

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Wingdale Hotel Deals

La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Aug 24 to Aug 25
CA $130
CA $150 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Overall the experience was outstanding"

Reviewed on Aug. 1, 2025

La Quinta Inn & Suites by Wyndham Danbury
Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

2 out of 5
80 Benedict Rd, Bethel, CT
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Aug 5 to Aug 6
CA $121
CA $140 total
Aug 5 - Aug 6
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"We arrived late and nothing around the area was open past 10 to get anything to eat."

Reviewed on Jul. 31, 2025

Microtel Inn & Suites by Wyndham Bethel/Danbury
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $175 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on Aug. 1, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 850 properties in Wingdale
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.
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Frequently asked questions

How much does a Wingdale vacation package cost?
Offering great value package deals from CA $768 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.