Pawling Holidays from £2,035
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Your Pawling Holiday
Our holiday packages to Pawling give you countless opportunities to immerse yourself in new sights, sounds and flavours. 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 holiday is just a few clicks away with Expedia.
Top Pawling Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
San Carlos Hotel
Manhattan
£2,220
per person
26 Oct - 31 Oct
found 7 hours ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9.6/10 Exceptional! (1,832 reviews)
Midtown, conveniently located and moderately priced hotel. Free water and WiFi was great. Staff couldn’t have been nicer and more accommodating
Reviewed on 21 Aug 2026
Pawling Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 2,300 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Stormville Airport Antique Show & Flea Market, John Kane House and Whaley Lake |
Top hotels in Pawling
Station Inn Pawling
7 Memorial Avenue Pawling NY
£123
20 Sept - 21 Sept
includes taxes & fees
9/10 Wonderful! (206 reviews)
"There should be a microwave somewhere in the building that a guest can use"
Reviewed on 14 Aug 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
£82
23 Aug - 24 Aug
includes taxes & fees
8/10 Very good! (1,416 reviews)
"We’ve stayed in many Connecticut hotels, and this is the cleanest of them all. Ethan Allen clearly takes pride in their brand, and this hotel proves it."
Reviewed on 20 Aug 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
£86
8 Sept - 9 Sept
includes taxes & fees
9/10 Wonderful! (1,050 reviews)
"Déjeuner vraiment bon et complet. Tout était bien les matelas de notre chambre était soso mais sinon tout était très bien"
Reviewed on 22 Aug 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
Daryl's House Club
You can enjoy a show at Daryl's House Club on 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 artefacts. Explore the Historical Society Museum upstairs and discover mounted birds in the Natural History Museum below.
Pawling Village Hall
Pawling Village Hall functions as the village's administrative centre, hosting community events and government activities. Visit on weekdays to see local governance in action or attend a public meeting.
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 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.
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.
Frequently asked questions
Why should I book my Pawling holiday with Expedia?
With top-value flights, accommodation and car hire options all in one place, Expedia makes booking your Pawling getaway a piece of cake. Moreover, we can help you bundle your bookings into a package holiday so you can enjoy even more savings. Select from amazing properties, add flights and/or a hire car (and maybe even some fun activities!) and get incredible prices. Need to change plans? Expedia has a flexible cancellation policy for many reservations. To find out more, check out our Customer Service Portal link.
When is the best time of year to holiday in Pawling?
If you'd like to experience the vibe of Pawling during peak season, plan your adventure for January, August and October. February, March and December are usually the quietest months of the year. To get an idea of the type of weather you can experience, the average temperature during the day in January, the coolest month in Pawling, is -2ºC. The warmest month here is July, when temperatures reach an average of 23ºC.
What is the top hotel for my holiday in Pawling?
Offering plenty of amenities and home comforts, Ramada by Wyndham Fishkill will make the perfect base for your Pawling escape.
How do I get a cheap holiday to Pawling?
Bundling your hotel and flight with Expedia won't just save valuable time — it'll save you a pretty penny too. A Pawling holiday makes it a cinch to organise the ideal trip. With more than 400 airlines around the world to select from, finding convenient flights that fit your schedule will be no sweat. In addition to that, we've got over 321,000 hotel options globally to pick from. Now that's what we call choice. Whatever your budget, Expedia brings the world within your reach. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Pawling holiday?
There are plenty of things to see and do while on your holiday in Pawling. Stormville Airport Antique Show & Flea Market, John Kane House, Whaley Lake and Beekman Golf Course are just some of this city's key attractions.
What is the best area to stay in when on holiday in Pawling?
If you plan to check out John Kane House, save yourself the hassle of commuting and book a stay close by. It's one of the best attractions in Pawling.
Do I need a visa for my Pawling holiday?
Visa requirements for Pawling vary depending on your nationality and the reason for your visit. It's best to check official government websites to determine if you need a visa for your holiday. They'll also give you the most up-to-date information, including details about application procedures or any supporting documentation that may be necessary. Enquire about your visa requirements well in advance to ensure a travel experience that's hassle free. Finally, make sure your passport is valid for at least six months from your planned date of return.
What should I wear on my Pawling holiday?
First, think about the sorts of activities you have planned during your holiday in Pawling and create a travel wardrobe that can be mixed and matched. For fashion inspiration or even information on dress codes, look up a few style blogs or social media accounts. Daytime temperatures during January, Pawling's coolest month, are around -2ºC. July marks this destination's warmest month when the average reaches 23ºC. Our suggestion? Take the guesswork out of what to pack and check the local weather conditions.
What does an Expedia Pawling holiday include?
Hotels, car hires and flights, or any combination of them — the choice is all yours! Whether you're headed to Pawling on a family road trip or travelling solo, there's a bundle to suit your budget and style. Once you've made your booking, why not add on one or two tours as well? Expedia features all sorts of properties, with the most popular in Pawling including private holiday homes and cottages. With Expedia, you'll always have the flexibility and freedom to tailor-make your holiday however you want.
Does Expedia offer Book Now, Pay Later Pawling holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find something that works with your budget. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that suit all types of budgets, so you can escape on that well-deserved holiday sooner.
- No-deposit holidays: If not paying upfront for your getaway makes clicking that "book now" button more stress-free, consider a no-deposit holiday plan from Klarna so you can Book Now, Pay Later!
Can I choose my airline with a Pawling Expedia holiday?
Yes — that's the beauty of an Expedia package. You get to choose. We have more than 400 airline partners throughout the world, so you have lots of choice when planning your Pawling trip.
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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. Flight-inclusive packages are ATOL protected.
