Pawling Vacations from $802
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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.
Hotel Riu Plaza Manhattan Times Square
Manhattan
$802
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
The staff is incredible, and the hotel is very lovely and centrally located; everything was exactly as it appears in the photos.
Reviewed on Oct 25, 2026
JW Marriott Essex House New York
Manhattan
$1,143
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!
Reviewed on Oct 19, 2026
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.
Daryl's House Club
You can make plans for a show at Daryl's House Club during your trip to Pawling.
Friends of Great Swamp
The Great Swamp offers a pristine 6,000-acre wetland sanctuary spanning two New York counties. Join Friends of the Great Swamp (FrOGS) for guided hikes and seasonal events showcasing the rich wildlife habitat.
Akin Free Library
This Victorian treasure houses both a library and museum with rare books and historical artifacts. Explore the Historical Society Museum upstairs and discover mounted birds in the Natural History Museum below.
Edward R Murrow Park
This serene 62-acre park honors broadcast journalism legend Edward R. Murrow with fishing docks and open fields. Enjoy the tranquil pond views or reserve the pavilion for special gatherings amid Pawling's natural beauty.
Pawling Free Library
The Pawling Free Library has served as a community learning hub since 1921, offering diverse collections and programs. Visitors can explore both buildings while attending seasonal workshops and cultural events.
Pawling Hotel Deals
Station Inn Pawling
7 Memorial Avenue Pawling NY
$143 nightly
$161 total
Nov 1 - Nov 2
Total with taxes and fees
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$104 nightly
$120 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (1,520 reviews)
"Great location, very clean room, and professional front desk staff. Overall, a pleasant and convenient stay!"
Reviewed on Oct 26, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
$109 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,144 reviews)
"The beds were terribly uncomfortable (lumpy) and the rooms were dingy,"
Reviewed on Oct 25, 2026
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 $802 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.
