Pawling Vacation Packages 2026 from $418

Pawling flight + hotel vacation packages

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

Delta Hotels by Marriott Woodbridge

$418

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking and a free area shuttle.

Seven Beach Lane

$1,154

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

2 bedroom luxury Empire State VIEW

Manhattan

$2,304

per person

Jun 25 - Jun 29

just found

Roundtrip flight included

Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

Topping Rose House

$1,542

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

Ace Hotel New York

Manhattan

Save 100% on your flight

$656

per person

Jul 9 - Jul 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This hotel features 2 coffee shops/cafes and a 24-hour gym. Enjoy a meal from the restaurant and perks like free WiFi. A bar/lounge, a 24-hour front desk, and express check-out are also provided.

Top Pawling hotels deals

Station Inn Pawling

7 Memorial Avenue Pawling NY

$149 nightly

$168 total

Apr 19 - Apr 20

Total with taxes and fees

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Best Western Danbury/Bethel

11 Stony Hill Road Bethel CT

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$95 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, along with the business center. Multilingual staff can provide around-the-clock assistance and free newspapers are on offer.

Breakfast included

Parking included

Hotel Zero Degrees Danbury

15 Milestone Road Danbury CT

$149 nightly

$171 total

Apr 19 - Apr 20

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

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

Apr 29 - Apr 30

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

Hampton Inn & Suites Poughkeepsie

2361 South Rd Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$123 total

Apr 26 - Apr 27

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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

25 OLD VINEYARD PLACE Hyde Park NY

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$182 total

May 10 - May 11

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Breakfast included

Pet friendly

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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

John Kane House

Find out about the history of Pawling with a stop at John Kane House. While in this trendy area, you can savor the top-notch restaurants.

Akin Free Library

Akin Free Library is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?

Pawling Town Hall

Pawling Town Hall is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?

Frequently asked questions

How much are vacation packages to Pawling?

Vacation packages, which include flights and hotels in Pawling, are priced from as little as $418. Make your travel dreams a reality and secure your dream vacation with Travelocity today.

How long should my Pawling vacation be?

If you need some guidance, most visitors spend an average of 2 nights vacationing in Pawling. But to uncover the true spirit of this destination, stay a bit longer. You'll be able to tick off more attractions and really soak up the local culture.

Where can I get the best vacation package deals for Pawling?

Travelocity is here to help you get a Pawling package deal. With no less than 400 partner airlines and 1,000,000 properties worldwide, you're bound to be able to put together the perfect itinerary.

Why should I purchase my Pawling vacation package via Travelocity?

With our Price Match Guarantee, we'll match any better price you find. Add to that our 24/7 support and top-quality service and your perfect vacation is well within reach.

Will I save money on my Pawling car rental if I combine it with my hotel or flight?

Bundling your car, hotel and flight into a Pawling vacation package is a great way to score an amazing deal. Plus, having your own set of wheels gives you total freedom to find your way to all those landmarks you want to see. Located 60 mi from Pawling, Times Square is one attraction that should be on your must-do list. Fasten your seat belt and make a day trip of it.

Which airport is best for Pawling?

There's a very good chance you'll arrive at LaGuardia Airport (LGA), located 55 mi south of downtown Pawling. Bradley Intl. Airport (BDL) (55 mi away from central Pawling) and MacArthur Airport (ISP) (60 mi away from central Pawling) are your other options.

What is there to do in Pawling?

Click away at the great photo opportunities at John Kane House, one of the most famous attractions in Pawling. There's a lot more to discover in this great destination, so give yourself enough time to visit some hidden gems.

Where should I stay when visiting Pawling?

The Station Inn Pawling is the number one choice of many visitors. Book soon before it's too late.