Pawling Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Pawling
Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York
Manhattan
€2,336
per person
9 Dec - 14 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (258 reviews)
Very interesting place. Unassuming on 39th Street but reasonably priced and quite a large room. Very charming with a lot of character and history. The bar was great.
Reviewed on 19 Oct 2026
Top hotels in Pawling
Station Inn Pawling
7 Memorial Avenue Pawling NY
€148
18 Nov - 19 Nov
includes taxes & fees
9.2/10 Wonderful! (214 reviews)
"It was a pleasure to stay there and the town is beautiful. Perfect location."
Reviewed on 12 Oct 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
€119
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (1,500 reviews)
"I was so very disappointed on our trip here from the moment we walked in we got there a little earlier and usually if a room is ready, they’ll check you in as soon as we got there she stopped us and said no you can’t check in until 3 o’clock it was very very rude. Totally get it. The room’s not ready. ..."
Reviewed on 20 Oct 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
€105
11 Nov - 12 Nov
includes taxes & fees
9/10 Wonderful! (1,126 reviews)
"👌"
Reviewed on 19 Oct 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.
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 enjoy a show at Daryl's House Club on 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 artefacts. 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 honours 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 programmes. Visitors can explore both buildings while attending seasonal workshops and cultural events.
Frequently asked questions
How much does a Pawling holiday package cost?
You'll find cheap prices from €1,390 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 holiday 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 holiday 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 holiday. 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 holiday package well in advance.
Is it cheaper to book a Pawling holiday as a package?
Expedia holiday 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 customised Pawling holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Pawling?
If you're considering a spontaneous Pawling holiday, 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?
- 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.
- Budget wisely: Besides the price of your accommodation, 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.
- 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.
- Combine your airfare and accommodation: After you've nailed down your dates and duration, book the perfect Pawling holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
