Pawling Vacations from $594
Book a Hotel + Flight or Car together to unlock savings
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.
The William Hotel Midtown, New York
Manhattan
$793
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.4/10 Exceptional! (232 reviews)
Such a well situated hotel slap bang in the middle of Manhattan, walking distance to most sightseeing/tourist hubs. Room was fantastic, spacious, tea/coffee making machine, fridge which was a bonus, would 100% stay here again. 5*
Reviewed on Sep 11, 2026
Stay near popular Pawling attractions
Daryl's House Club
You can make plans for a show at Daryl's House Club during your trip to Pawling.
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.
Pawling Town Hall
Pawling Town Hall functions as the administrative heart of this New York community, hosting public meetings and essential services. Visit during weekday business hours to connect with local governance in action.
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.
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.
Pawling Village Hall
Pawling Village Hall functions as the village's administrative center, hosting community events and government activities. Visit on weekdays to see local governance in action or attend a public meeting.
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.
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 Hotel Deals
Station Inn Pawling
7 Memorial Avenue Pawling NY
$156 nightly
$176 total
Sep 13 - Sep 14
Total with taxes and fees
9.2/10 Wonderful! (210 reviews)
"Newly renovated. Very clean! Very cozy too. Staff is very helpful. Love everything."
Reviewed on Sep 6, 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
$115 nightly
$132 total
Sep 27 - Sep 28
Total with taxes and fees
8/10 Very Good! (1,432 reviews)
"This was our fourth visit to the hotel and I’ve never had an issue prior but this visit I was extremely disappointed.. the hotel seemed to be overbooked due to two weddings and a birthday party going on .. front desk staff were non engaging .. the one was so focused on her computer screen … I reserved ..."
Reviewed on Sep 12, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$101 nightly
$117 total
Sep 22 - Sep 23
Total with taxes and fees
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 $594 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.