Pawling Vacations from $959

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Your Pawling Vacation

Our vacation packages to Pawling give you countless opportunities to immerse yourself in new sights, sounds and flavors. And with all the travel planning taken care of, you can chill out and enjoy your city getaway in the way that you deserve. Love to explore your surroundings? Thunder Ridge Ski Resort, Whaley Lake and Lake Dutchess are just three of the top-rated places to visit during your trip to Pawling. Whoever you're taking time off with and whatever your bank balance, your dream Pawling vacation is just a few clicks away with Expedia.

The Latest Pawling vacation packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,569, price is now $959 per person
$959
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $2,395, price is now $1,363 per person
$1,363
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was $2,024, price is now $1,187 per person
$1,187
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8/10 Very Good! (1,000 reviews)
Completely caught off guard by this property: The Expedia photos looked great, the lobby was fine but the actual room was shabby and sub-par. The room and bathroom had the bare minimum amenities, smelled of stale cigarette smoke and was generally below expectations. Probably ok for a budget vacationer but I’m making a note to avoid this for a work stay.

Reviewed on Nov 11, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,808, price is now $1,651 per person
$1,651
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $2,091, price is now $1,309 per person
$1,309
per person
Jan 17 - Jan 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

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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

Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
$138 nightly
The price is $156 total per night from Dec 16 to Dec 17
$156 total
Dec 16 - Dec 17
Total with taxes and fees
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
$101 nightly
The price is $116 total per night from Dec 6 to Dec 7
$116 total
Dec 6 - Dec 7
Total with taxes and fees
Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $111 total per night from Nov 29 to Nov 30
$111 total
Nov 29 - Nov 30
Total with taxes and fees
Best Western Danbury/Bethel
See all 859 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.

Find the Best Pawling Vacation Packages

Pawling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
2,300
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Stormville Airport Antique Show & Flea Market, Whaley Lake and John Kane House

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Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices from $959 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?
You're likely to find lower prices and better availability in February, March and December. Explore our cheap Pawling vacation packages and you could land some excellent off-season deals.
How many days is enough for Pawling?
With a well-organized schedule, you can easily tick off the most popular Pawling sights in a few days. But if you prefer to explore off the beaten track or go on day trips, consider booking your Pawling vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Pawling vacation packages?
Jet off on your dream getaway to Pawling with Expedia's Book Now, Pay Later vacations. No need to save up or wait until the next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up cheap deals before they sell out.

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