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A wooden boardwalk with a wooden chair and a sign reading "Swamp River Boardwalk."

Pawling Holidays from AU$3,204

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Pawling holiday deals

Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    2 Oct - 8 Oct

    EVEN Hotel Brooklyn by IHG + Flight

    Brooklyn
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,941 reviews)
    Return • Sydney (SYD) - New York (JFK)
    SYD - LGA • 2 stops EWR - SYD • 1 stop
    AU$3,810
    AU$3,204
    per traveller
    found 1 day ago
    EVEN Hotel Brooklyn by IHG
  • Front of property
    2 Oct - 8 Oct

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    6 nights
    4.0 star property
    9.0/10 - Wonderful (3,213 reviews)
    Return • Sydney (SYD) - New York (JFK)
    SYD - LGA • 2 stops EWR - SYD • 1 stop
    AU$5,440
    AU$3,756
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • Room, 1 King Bed (City View or Courtyard View)
    2 Oct - 8 Oct

    NobleDEN Hotel + Flight

    Manhattan
    6 nights
    4.0 star property
    9.6/10 - Exceptional (1,620 reviews)
    "This hotel is adorable. Great location. Rooms are a great size. We will be back!"
    Reviewed July 17, 2026
    Return • Sydney (SYD) - New York (JFK)
    SYD - LGA • 2 stops EWR - SYD • 1 stop
    AU$4,779
    AU$3,688
    per traveller
    found 1 day ago
    NobleDEN Hotel
  • Property entrance
    2 Oct - 8 Oct

    Sela V Hotel + Flight

    Brooklyn
    6 nights
    4.0 star property
    9.4/10 - Exceptional (41 reviews)
    "staff was friendly and helpful. Room was clean and comfortable."
    Reviewed July 17, 2026
    Return • Sydney (SYD) - New York (JFK)
    SYD - LGA • 2 stops EWR - SYD • 1 stop
    AU$4,350
    AU$3,519
    per traveller
    found 1 day ago
    Sela V Hotel
  • Frette Italian sheets, premium bedding, down duvets, pillow-top beds
    2 Oct - 8 Oct

    The Iroquois Times Square, a Small Luxury Hotel + Flight

    Manhattan
    6 nights
    4.5 star property
    9.6/10 - Exceptional (1,757 reviews)
    "My family chose this hotel because we were in town for the Jay Z Blueprint 25 concert. Paulisha checked us in early and gave us a room upgrade. We enjoyed our stay at this boutique hotel that was walking distance from Time Square and other attractions and restaurants. We were greeted every time we came and went, provided umbrellas for rainy days, breakfast vouchers, refreshing water in the lobby and happy hour on a Thursday evening. We will be staying here again and I prefer our same room for..."
    Reviewed July 18, 2026
    Return • Sydney (SYD) - New York (JFK)
    SYD - LGA • 2 stops EWR - SYD • 1 stop
    AU$4,753
    AU$3,856
    per traveller
    found 1 day ago
    The Iroquois Times Square, a Small Luxury Hotel

Discover the most popular places to visit in 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 Hotel Deals

Terrace/patio

Station Inn Pawling

Station Inn Pawling
3.0 star property
0.2 km from Pawling
9.2 out of 10, Wonderful, (205 reviews)
"Perfect place to stay the night. You can hear the train passing by, but there are ear plugs and a white noise machine in the room. It didn't bother us at all, but it might other folks"
The price is AU$233
includes taxes & fees
16 Aug - 17 Aug
Station Inn 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.
See all properties in Pawling

Frequently Asked Questions

How much does a Pawling holiday package cost?

You'll find cheap prices from AU$3,204 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.