Pawling Holidays from AU$1,133

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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.
Arlo SoHo

Arlo SoHo

4 out of 5
Manhattan
Save 100% on your flight
per person
20 Oct - 23 Oct
found 20 hours ago
Return flight included
Los Angeles (LAX) to New York (JFK)
8.8/10 Excellent! (1,818 reviews)
Seamless experience throughout my entire stay. The amenities are awesome & staff is extremely attentive.

Reviewed on 18 Aug. 2025

Crowne Plaza HY36 Midtown Manhattan by IHG

Crowne Plaza HY36 Midtown Manhattan by IHG

4 out of 5
Manhattan
Save 100% on your flight
per person
20 Oct - 23 Oct
found 20 hours ago
Return flight included
Los Angeles (LAX) to New York (JFK)
9.2/10 Wonderful! (1,968 reviews)
No complaints. Helpful staff, clean rooms, big rooms. Great for a stay in new york

Reviewed on 17 Aug. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 20 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul. 2025

The Mark

The Mark

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 20 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (678 reviews)
This is a perfect location!

Reviewed on 17 Aug. 2025

Waldorf Astoria New York

Waldorf Astoria New York

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 20 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
No reviews

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$373 per night from 19 Aug to 20 Aug
AU$373
19 Aug - 20 Aug
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$184 per night from 8 Sept to 9 Sept
AU$184
8 Sept - 9 Sept
includes taxes & fees
7.6/10 Good! (392 reviews)
"Nice."

Reviewed on 15 Aug. 2025

Quality Inn Poughkeepsie
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension, I-84 at Exit 4, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 24 Aug to 25 Aug
AU$172
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Good"

Reviewed on 14 Aug. 2025

Ethan Allen Hotel
See all 832 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$1,133 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.