Pawling Holidays from NZ$4,080
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The Latest Pawling Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Lombardy Hotel
Manhattan
NZ$4,964
per person
5 Oct - 12 Oct
found 17 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,560 reviews)
The staff were wonderful (Shout out to all the reception staff, also Shawn, Cesar and Jimmy)
Cleaning quality varied depending on who was on duty, but for a longer stay I would still highly recommend this hotel!
Reviewed on 21 Aug 2026
Margaritaville Resort Times Square
Manhattan
NZ$4,870
per person
5 Oct - 12 Oct
found 19 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (4,305 reviews)
Every aspect about this Hotel is SUPERIOR. Can't say I've ever stayed anywhere recently when ALL details were so carefully maintained! And your staff must love their work because they are consistently gracious. The ambience is definitely RESORT!
Reviewed on 21 Aug 2026
The Shelburne Sonesta New York
Manhattan
NZ$4,616
per person
5 Oct - 12 Oct
found 19 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,043 reviews)
Great location! I loved the stay but our air conditioning was leaking water the whole time. So the floor was always wet. Otherwise- great hotel, great location and I would stay there again!
Reviewed on 20 Aug 2026
Pawling Holiday
Our pick of the best Pawling Hotel Deals
Station Inn Pawling
7 Memorial Avenue Pawling NY
NZ$283
20 Sept - 21 Sept
includes taxes & fees
9/10 Wonderful! (206 reviews)
"There should be a microwave somewhere in the building that a guest can use"
Reviewed on 14 Aug 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
NZ$188
23 Aug - 24 Aug
includes taxes & fees
8/10 Very good! (1,416 reviews)
"We’ve stayed in many Connecticut hotels, and this is the cleanest of them all. Ethan Allen clearly takes pride in their brand, and this hotel proves it."
Reviewed on 20 Aug 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
NZ$205
10 Sept - 11 Sept
includes taxes & fees
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 Pawling attractions
Daryl's House Club
You can enjoy a show at Daryl's House Club on your trip to Pawling.
John Kane House
This Revolutionary War headquarters of General Washington offers an intimate glimpse into 18th-century American history. Explore exhibits while volunteer guides bring the past to life.
Pawling Town Hall
Pawling Town Hall functions as the administrative heart of this New York community, hosting public meetings and essential services. Visit during weekday business hours to connect with local governance in action.
Akin Free Library
This Victorian treasure houses both a library and museum with rare books and historical artefacts. Explore the Historical Society Museum upstairs and discover mounted birds in the Natural History Museum below.
Pawling Village Hall
Pawling Village Hall functions as the village's administrative centre, hosting community events and government activities. Visit on weekdays to see local governance in action or attend a public meeting.
Friends of Great Swamp
The Great Swamp offers a pristine 6,000-acre wetland sanctuary spanning two New York counties. Join Friends of the Great Swamp (FrOGS) for guided hikes and seasonal events showcasing the rich wildlife habitat.
Pawling Free Library
The Pawling Free Library has served as a community learning hub since 1921, offering diverse collections and programs. Visitors can explore both buildings while attending seasonal workshops and cultural events.
Edward R Murrow Park
This serene 62-acre park honours broadcast journalism legend Edward R. Murrow with fishing docks and open fields. Enjoy the tranquil pond views or reserve the pavilion for special gatherings amid Pawling's natural beauty.
Frequently asked questions
How much does a Pawling holiday package cost?
You'll find cheap prices from NZ$4,080 on Expedia for your Pawling escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Pawling costs.
What are the cheapest months to go to Pawling?
Plan your getaway for the off-season and you're likely to score cheap Pawling holiday packages. Bear in mind that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Pawling?
Generally, a handful of days is enough to tick off the major sights during your Pawling holiday. But if you'd like to have some time to unwind or take day tours, think about extending your trip.
How to find the best Pawling package deals?
Use Expedia's filters to find some great Pawling package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Pawling package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Pawling holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customised Pawling holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Pawling?
If you're considering a spontaneous Pawling holiday, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Pawling?
- Choose when to get away: Check your calendar and get packing. Your preferred season and the type of activities available will also help you decide when to visit Pawling.
- Budget wisely: Besides the price of your accommodation, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Pawling.
- Work out your trip length: Consider how much time you want to spend exploring Pawling. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Combine your airfare and accommodation: After you've nailed down your dates and duration, book the perfect Pawling holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
