Pawling Holidays
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Top Flight + Hotel Deals in Pawling
Price found within the past 48 hours. Click for updated prices.
YOTEL New York Times Square
Manhattan
€954
per person
14 Oct - 17 Oct
found 24 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
7.8/10 Good! (2,995 reviews)
Our stay at YOTEL was unfortunately a very frustrating experience.
The hotel itself was nice and the location was convenient for our New York trip. The room was modern and the hotel had a fun, unique atmosphere. However, our experience with the reservation and customer service really took away from the overall stay.
Our flight was significantly delayed, which caused us to miss our original check-in time. Because of the flight delay, the hotel marked our reservation as a no-show. We ended up having to make another reservation at the last minute, costing us around $800, even though we had a legitimate travel delay and were still planning to stay at the hotel.
What was especially frustrating was having to deal with the financial consequences of something that was completely outside of our control. We spent a lot of time trying to get the situation resolved, and it made an already stressful travel day even more difficult.
While I liked the hotel and its location, I expected more understanding and flexibility from the hotel given the circumstances. Unfortunately, the way the situation was handled left a bad impression and would make me hesitant to stay at YOTEL again.
The hotel itself has potential, but customer service and how unexpected travel disruptions are handled need improvement.
Reviewed on 4 Sept 2026
Top hotels in Pawling
Station Inn Pawling
7 Memorial Avenue Pawling NY
€151
4 Oct - 5 Oct
includes taxes & fees
9.2/10 Wonderful! (209 reviews)
"Very nice inn. Operated like an Airbnb and no notices of check in procedure received via Expedia. Glad staff was nearby and available when we were checking in. No staff on site."
Reviewed on 3 Sept 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
€115
20 Sept - 21 Sept
includes taxes & fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
€97
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Hotel is in good shape with a good breakfast."
Reviewed on 4 Sept 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.
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 centre, 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 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
How much does a Pawling holiday package cost?
You'll find cheap prices from €848 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.
