Wingdale Holidays from £948

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Wingdale Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
414 hotel

414 hotel

2 out of 5
Manhattan
Price was £1,458, price is now £948 per person
£948
per person
15 Jan - 21 Jan
found 23 hours ago
Return direct flight included
London (LON) to New York (JFK)
6/10 (276 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was £2,666, price is now £1,658 per person
£1,658
per person
4 Feb - 7 Feb
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on 6 Nov 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,889, price is now £1,830 per person
£1,830
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The bar cafe in the lobby was amazing! Quick check in, clean property and very spacious rooms for this price point in NYC

Reviewed on 13 Nov 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was £1,677, price is now £1,069 per person
£1,069
per person
20 Jan - 25 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,729, price is now £1,750 per person
£1,750
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

Wingdale Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
2ºC
Max Temp Summer
27ºC

Top hotels in Wingdale

Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is £95 per night from 13 Dec to 14 Dec
£95
13 Dec - 14 Dec
includes taxes & fees
8/10 Very good! (1,559 reviews)
"The downstairs was absolutely beautiful. The elevator was disgusting and sticky and gross. The room was just OK, I was actually pretty disappointed. Very out of date, old, dirty carpeting. The furniture needs to be replaced. Which was surprising because it is so beautiful downstairs. It felt like ..."

Reviewed on 12 Nov 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is £84 per night from 30 Nov to 1 Dec
£84
30 Nov - 1 Dec
includes taxes & fees
Best Western Danbury/Bethel
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is £82 per night from 13 Dec to 14 Dec
£82
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,165 reviews)
"Wonderful breakfast! Beautiful, clean room! Will stay here again!!!"

Reviewed on 12 Nov 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 876 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Wingdale attractions

Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
See properties

Frequently asked questions

How much does a Wingdale travel package cost?
We make it simple to travel the world, with Wingdale travel packages starting from as little as £948. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a couple of tours and activities to your travel itinerary?
If I'm not able to travel, can I cancel my Wingdale travel package?
It's hard to predict what the future holds, so it's comforting to know that you can cancel or change your Wingdale travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Wingdale?
You'll save a ton of money if you bundle your car rentals, flights and hotels into a Wingdale travel package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, which means you'll always have plenty of variety to choose from. Eager to save even more? Add some interesting activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Wingdale holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all types of budgets, so you can have that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan from Klarna.

What are the top hotels in Wingdale?
HYATT house Fishkill/Poughkeepsie and Hyatt Place Poughkeepsie are among the most popular properties in Wingdale. Why not look up the rates and facilities at each and then make up your mind?
How far in advance should I book my Wingdale holiday?
Savvy travellers will likely want to book early. You can generally compare international airfares on Expedia up to 12 months before your flight. If you're purchasing tickets last minute, don't stress. Low prices occasionally occur in the last weeks before departure.
What does an Expedia Wingdale travel package include?
Rental cars, hotels and flights — you'll find them all here. With Expedia, you can shape your Wingdale package however you want. All you have to do is determine just what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the more you save!
What should I know before booking a Wingdale travel package?
Whether it's adventure or relaxation you're seeking, a Wingdale travel package lets you plan your escape your way. Plus, you'll score great discounts just for combining your accommodation with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Wingdale Expedia travel package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply select your preferred air carrier and craft the perfect Wingdale holiday.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.