Pawling Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Pawling Vacation Packages

Pawling Hotel Deals

Station Inn Pawling
Station Inn Pawling
3 out of 5
7 Memorial Avenue, Pawling, NY
The price is ₩330,459 per night from Jul 25 to Jul 26
₩330,459
₩373,826 total
Jul 25 - Jul 26
includes taxes & fees
9/10 Wonderful! (171 reviews)
Pleasant and convenient.
"We have stayed here many times. Always low key, clean and cozy. Trains go by infrequently at night. Hasn’t been disruptive. We like to stay after going to show at Darryl’s house."

Reviewed on Mar 9, 2025

Station Inn Pawling
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is ₩150,758 per night from Jul 1 to Jul 2
₩150,758
₩170,545 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Nothing"

Reviewed on Jun 23, 2025

HYATT house Fishkill/Poughkeepsie
Hampton Inn & Suites Poughkeepsie
Hampton Inn & Suites Poughkeepsie
2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is ₩150,011 per night from Jul 9 to Jul 10
₩150,011
₩174,201 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Great room"

Reviewed on Jun 24, 2025

Hampton Inn & Suites Poughkeepsie
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.

Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices 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 vacation 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 vacation 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 vacation. 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 vacation package well in advance.
Is it cheaper to book a Pawling vacation as a package?
Expedia vacation 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 customized Pawling vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pawling?
If you're considering a spontaneous Pawling vacation, 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 accommodations, 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 accommodations: After you've nailed down your dates and duration, book the perfect Pawling vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.