Pawling Vacations from $399

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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.
Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
Save 100% on your flight
Price was $665, price is now $399 per person
$399
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,001 reviews)
Beautiful facility. 2 Queen rooms spacious. Comfortable beds and rooms were updated and clean.

Reviewed on Oct 12, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $882, price is now $483 per person
$483
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,880, price is now $1,069 per person
$1,069
per person
Dec 24 - Dec 27
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Nice hotel , needs a bit of tender love and care !

Reviewed on Oct 14, 2025

Pocono Mountain Villas by Exploria Resorts

Pocono Mountain Villas by Exploria Resorts

3.5 out of 5
Save 100% on your flight
Price was $679, price is now $405 per person
$405
per person
Dec 7 - Dec 14
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (916 reviews)
Me encantó estar aquí muy buen servicio los cuartos limpios

Reviewed on Oct 15, 2025

Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,126, price is now $1,271 per person
$1,271
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (795 reviews)
Great area nice property

Reviewed on Sep 30, 2025

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Discover the most popular places to visit in Pawling

John Kane House

Find out about the history of Pawling with a stop at John Kane House. While in this trendy area, you can savor the top-notch restaurants.

John Kane House

Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue, Pawling, NY
$225 nightly
The price is $254 total per night from Nov 16 to Nov 17
$254 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (178 reviews)
"Very clean."

Reviewed on Jul 4, 2025

Station Inn Pawling
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
$110 nightly
The price is $128 total per night from Nov 2 to Nov 3
$128 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,028 reviews)
Breakfast was good
"Housekeeper did a great job. The breakfast was the correct way, a meat item everyday (unlike some locations) and good selection."

Reviewed on Oct 15, 2025

Hampton Inn & Suites Poughkeepsie
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
$84 nightly
The price is $96 total per night from Nov 2 to Nov 3
$96 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,010 reviews)
"Everything is decent."

Reviewed on Oct 10, 2025

Best Western Danbury/Bethel
See all 820 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.

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 $399 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.

Explore a world of travel with Expedia

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