Pawling Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ฿4,531 when you book a flight and hotel together*
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Top Pawling Flight + Hotel Deals

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

Hudson Yards Hotel

2 out of 5
Manhattan
per person
8 Sept - 10 Sept
found 1 day ago
Return direct flight included
Fort Walton Beach (VPS) to New York (JFK)
6.8/10 (722 reviews)
The property location was great and the staff were very nice. The room itself was very dark and there were no power outlets accessible from the night stands or desk. The one power outlet was by the door and it was so loose my charger fell out and so it was a real problem to charge my phone and devices. This caused an issue for me so while the hotel was clean and in a great location I am not sure I would choose to stay here again.

Reviewed on 29 Jul 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
8 Sept - 10 Sept
found 1 day ago
Return direct flight included
Fort Walton Beach (VPS) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Our stay was amazing. Highly recommend. We'll be staying again.

Reviewed on 31 Jul 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
8 Sept - 10 Sept
found 1 day ago
Return direct flight included
Fort Walton Beach (VPS) to New York (JFK)
9.2/10 Wonderful! (3,398 reviews)
Very close to everything in Manhattan. Clean, modern, great breakfast

Reviewed on 31 Jul 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
8 Sept - 10 Sept
found 1 day ago
Return direct flight included
Fort Walton Beach (VPS) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
Great design in rooms

Reviewed on 1 Aug 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
per person
8 Sept - 10 Sept
found 1 day ago
Return direct flight included
Fort Walton Beach (VPS) to New York (JFK)
8.8/10 Excellent! (6,073 reviews)
Such a friendly, classic place to stay in NYC

Reviewed on 1 Aug 2025

Top hotels in Pawling

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue, Pawling, NY
The price is ฿6,983 per night from 3 Aug to 4 Aug
฿6,983
฿7,899 total
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (174 reviews)
"Very clean."

Reviewed on 4 Jul 2025

Station Inn Pawling
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is ฿3,069 per night from 24 Aug to 25 Aug
฿3,069
฿3,529 total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Great place for family staff is so friendly and accommodating the minute you check in Diane was at the desk just so inviting and welcoming …we were looking for a family gathering ite for the holidays I think we definitely found it!!"

Reviewed on 30 Jul 2025

La Quinta Inn & Suites by Wyndham Danbury
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is ฿3,543 per night from 17 Aug to 18 Aug
฿3,543
฿4,115 total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on 1 Aug 2025

Holiday Inn Express Poughkeepsie by IHG
See all 839 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.

Frequently asked questions

How much does a Pawling holiday package cost?
You'll find cheap prices from ฿19,254 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.