Pawling Holidays from AU$3,145

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Your Pawling Holiday

With a Pawling holiday package, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before departing, so you can enjoy each moment experiencing this exciting city. Want to start exploring your surroundings? Thunder Ridge Ski Resort, John Kane House and Whaley Lake are some of the top-rated places to visit during a trip to Pawling. Browse Expedia's extensive range of travel options and book your ideal holiday to Pawling now.

The Latest Pawling Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was AU$4,626, price is now AU$3,145 per person
AU$3,145
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8/10 Very Good! (2,142 reviews)
This hotel offers some rooms with a kitchen so you can prepare your own meals if, like me, you prefer to keep your costs low by eating in instead of out. The room I had was perfect for that. Check-in was easy and quick; and the location was quite convenient for me.

Reviewed on 25 Aug. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was AU$5,284, price is now AU$3,515 per person
AU$3,515
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,293 reviews)
Great people, great place, rooms are spot on and Rooftop is worth every penny

Reviewed on 26 Aug. 2025

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 AU$4,879, price is now AU$3,326 per person
AU$3,326
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.6/10 Excellent! (1,083 reviews)
Excellent location and great staff

Reviewed on 26 Aug. 2025

The William Vale

The William Vale

5 out of 5
Price was AU$5,979, price is now AU$4,152 per person
AU$4,152
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (1,005 reviews)
The pool was nice but you can only sit in the lounge chairs for 2 hours and then they make you get up. I was told, prior to me booking, that there was a DJ playing the night we stayed that played to 2 am. There was no DJ, so that was disappointing.

Reviewed on 27 Aug. 2025

The Dominick

The Dominick

5 out of 5
Manhattan
Save 100% on your flight
Price was AU$7,417, price is now AU$5,274 per person
AU$5,274
per person
11 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Room made service , room service, front, bell man service

Reviewed on 25 Aug. 2025

Pawling Holiday

Pawling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
2,300
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Stormville Airport Antique Show & Flea Market, John Kane House and Whaley Lake

Our pick of the best Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue, Pawling, NY
The price is AU$409 per night from 25 Sept to 26 Sept
AU$409
25 Sept - 26 Sept
includes taxes & fees
9/10 Wonderful! (176 reviews)
"Very clean."

Reviewed on 4 Jul. 2025

Station Inn Pawling
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 21 Sept to 22 Sept
AU$182
21 Sept - 22 Sept
includes taxes & fees
7.6/10 Good! (403 reviews)
"Overall good stay"

Reviewed on 24 Aug. 2025

Quality Inn Poughkeepsie
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 out of 5
849 Route 52, Fishkill, NY
The price is AU$168 per night from 7 Sept to 8 Sept
AU$168
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
Brittany is a gem!
"Very helpful front desk was lovely! Brittany was supportive re: a rental car issue we had when it was not her problem!! Brittany always smiled and made us feel welcome in our coming and goings!!"

Reviewed on 24 Aug. 2025

Quality Inn & Suites Fishkill South near I-84
See all 833 properties in Pawling
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Pawling holiday package cost?
You'll find cheap prices from AU$3,145 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.