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.
Dolce by Wyndham Parsippany

Dolce by Wyndham Parsippany

4 out of 5
Save 100% on your flight
Price was $630, price is now $329 per person
$329
per person
Dec 31 - Jan 5
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. Traveling on business? Take advantage of the business center and WiFi in public areas. Enjoy the indoor pool and perks like free self parking.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,280, price is now $1,097 per person
$1,097
per person
Dec 8 - Dec 11
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,966, price is now $1,066 per person
$1,066
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,686, price is now $1,548 per person
$1,548
per person
Dec 28 - Jan 2
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. WiFi in public areas is free. There's dry cleaning and multilingual staff can provide around-the-clock assistance.
Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

3.5 out of 5
Save 100% on your flight
Price was $725, price is now $431 per person
$431
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A casino and a restaurant are featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Valet parking, a coffee shop, and dry cleaning are also offered.

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
$104 nightly
The price is $120 total per night
$120 total
Nov 1 - Nov 2
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
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
$99 nightly
The price is $115 total per night
$115 total
Nov 22 - Nov 23
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
Breakfast included
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $149 total per night
$149 total
Nov 1 - Nov 2
Total with taxes and fees
A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.
Pool
Hot Tub
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Free Cancellation
$105 nightly
The price is $122 total per night
$122 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features an indoor pool and a 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
Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

2.5 out of 5
80 Newtown Road Danbury CT
Free Cancellation
$115 nightly
The price is $132 total per night
$132 total
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. 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
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road Danbury CT
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $126 total per night
$126 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet 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.

Stay near popular Wingdale attractions

Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
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Frequently asked questions

How much are vacation packages to Wingdale?
Your travel dreams can come to life in Wingdale from as little as $329. 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

A weathered window with a view of trees and a building in the background.