Pawling Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Pawling Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Price was S$4,151, price is now S$3,303 per person
S$3,303
per person
15 Dec - 22 Dec
found 13 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
7.8/10 Good! (3,136 reviews)
Staff was very helpful, attentive and kind. Clean room. Small but perfect for two!

Reviewed on 4 Nov, 2026

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was S$4,885, price is now S$3,579 per person
S$3,579
per person
15 Dec - 22 Dec
found 13 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was S$5,457, price is now S$4,051 per person
S$4,051
per person
15 Dec - 22 Dec
found 13 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (4,191 reviews)

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was S$4,615, price is now S$3,654 per person
S$3,654
per person
15 Dec - 22 Dec
found 13 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (2,296 reviews)
Easy check-in, convenient location, with access the entire city with a few-minute walk to subways and LIRR.

Reviewed on 4 Nov, 2026

Hilton Garden Inn New York/Manhattan-Chelsea

Hilton Garden Inn New York/Manhattan-Chelsea

3 out of 5
Manhattan
Price was S$4,723, price is now S$3,771 per person
S$3,771
per person
15 Dec - 22 Dec
found 13 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8/10 Very good! (3,180 reviews)
Overall for the price it was a great deal. It’s not a five diamond five star resort, but for what it offered it was worth it. A clean and safe place to lay your head down in the city. No frills but not bad just clean and simple. It served its purpose. Breakfast in the morning was extra but even it offered what the city could not. An affordable meal that gives everyone what they want all you can eat and great service. Overall this was a great place at an affordable price (for NYC)

Reviewed on 4 Nov, 2026

Top hotels in Pawling

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
The price is S$199 per night from 3 Dec to 4 Dec
S$199
3 Dec - 4 Dec
includes taxes & fees
9.2/10 Wonderful! (217 reviews)
"Tidy small inn and very comfortable. Coffee and tea were available at a station in the hall as well as in each room. Easy to come and go. Small restaurants and coffee shop are within easy walking distance."

Reviewed on 31 Oct, 2026

Station Inn Pawling
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is S$159 per night from 22 Nov to 23 Nov
S$159
22 Nov - 23 Nov
includes taxes & fees
Ethan Allen Hotel
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is S$139 per night from 29 Nov to 30 Nov
S$139
29 Nov - 30 Nov
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
See all 850 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.

Stay near popular Pawling attractions

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.
See properties

Frequently asked questions

How much does a Pawling holiday package cost?
You'll find cheap prices from S$3,303 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.