Deals on vacations and trips to Wingdale

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Wingdale flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $564, price is now $307 per person
$307
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and rooftop terrace.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,054, price is now $447 per person
$447
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.
Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was $1,149, price is now $569 per person
$569
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $877, price is now $447 per person
$447
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,551, price is now $843 per person
$843
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the steam room, bar/lounge, and concierge services.

Top Wingdale hotels deals

Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $106 total per night
$106 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free train station pick-up. Enjoy the seasonal outdoor pool and perks like free self parking.
Pool
Pet friendly
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $194 total per night
$194 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a terrace, and dry cleaning are also offered.
Pet friendly
Parking included
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $118 total per night
$118 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $137 total per night
$137 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $103 total per night
$103 total
Dec 26 - Dec 27
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Free WiFi
Restaurant
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $108 total per night
$108 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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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.

Popular places to visit

Olivet University

Walk around the campus at Olivet University during your stay in Wingdale.

Olivet University

Dover Veterans Memorial Library

After visiting Dover Veterans Memorial Library, make a plan to see the other sights and activities in Wingdale.

Dover Veterans Memorial Library

Leather Hill Preserve

You can take time to visit Leather Hill Preserve during your travels to Wingdale.

Leather Hill Preserve

Frequently asked questions

How much are vacation packages to Wingdale?
Your travel dreams can come to life in Wingdale from as little as $307. Our packages include flights and hotels, so you'll find booking is a cinch. All you'll have to focus on is having an incredible time.
Where can I get the best vacation package deals for Wingdale?
For an amazing Wingdale package deal, head straight to Travelocity. Take your pick of 400 airlines and 1,000,000 worldwide properties to create your ideal adventure — you're spoiled for choice!
Why should I book my Wingdale vacation package via Travelocity?
With fantastic service, customer support available 24/7 and some of the most perfect escapes around, you'll never roam alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Wingdale car rental if I book it with a hotel or flight?
Combining your flight, car and hotel into a Wingdale vacation package is a surefire way to land the best prices. Plus, having your own wheels gives you absolute freedom to find your way to all the landmarks you're itching to see. Located 65 mi from Wingdale, Times Square is one place that should be on your can't-miss list. Top up the tank and make a day trip of it.
Which airport is best for Wingdale?
It's likely you'll arrive at Bradley Intl. Airport (BDL), located 50 mi northeast of inner Wingdale. Tweed - New Haven Regional Airport (HVN) (45 mi away from central Wingdale) and Stewart Intl. Airport (SWF) (30 mi away from central Wingdale) are your other choices.
Where should I stay when visiting Wingdale?
Many people hit the hay at the Country House. It's sure to be a good base for your Wingdale getaway.

Photos of local treasures

Browse Wingdale vacation photos for more inspiration

Photo by Anna Arsenault
Photo by Anna Arsenault