Pawling Vacation Packages 2026 from $354

Pawling flight + hotel vacation packages

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

DoubleTree by Hilton Hotel Newark Airport

Save 100% on your flight

$354

per person

May 9 - May 13

found 1 day ago

Roundtrip flight included

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

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Unwind with a drink at the bar/lounge and enjoy free perks like WiFi in public areas and a roundtrip airport shuttle. Self parking, a 24-hour business center, and express check-out are also offered.

Hotel St. James

Manhattan

Save 100% on your flight

$444

per person

May 6 - May 9

found 1 day ago

Roundtrip flight included

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

Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

1 Hotel Brooklyn Bridge

$2,073

per person

May 28 - Jun 1

found 13 hours ago

Roundtrip flight included

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

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$662

per person

May 6 - May 9

found 1 day ago

Roundtrip flight included

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

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. Enjoy the free buffet breakfast each morning.

Sheraton New York Times Square Hotel

Manhattan

Save 100% on your flight

$397

per person

May 6 - May 9

found 1 day ago

Roundtrip flight included

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

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Top Pawling hotels deals

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

$179 nightly

$206 total

Mar 29 - Mar 30

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

2361 South Rd Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$134 total

Apr 3 - Apr 4

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

Courtyard by Marriott Fishkill

17 Westage Drive Fishkill NY

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$114 total

Mar 30 - Mar 31

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and a snack bar/deli are also offered.

Parking included

Free WiFi

Heritage Hotel, Golf & Conference Center

522 Heritage Road Southbury CT

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$155 total

Mar 29 - Mar 30

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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

25 OLD VINEYARD PLACE Hyde Park NY

$151 nightly

$171 total

Apr 27 - Apr 28

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.

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?

Friends of Great Swamp

You can take time to visit Friends of Great Swamp during your travels to Pawling.

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 $354. 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.