Pawling Holidays from £1,246

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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.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,211, price is now £1,246 per person
£1,246
per person
18 Sept - 23 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
Good Location

Reviewed on 26 Jul 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,312, price is now £1,295 per person
£1,295
per person
18 Sept - 23 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,226 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,675, price is now £1,531 per person
£1,531
per person
3 Oct - 10 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9.8/10 Exceptional! (1,630 reviews)
The staff were very attentive to us during our stay. The room was very clean and the balcony was beautiful. 10/10

Reviewed on 25 Jul 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,636, price is now £2,104 per person
£2,104
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9.2/10 Wonderful! (687 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £5,180, price is now £3,276 per person
£3,276
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

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

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
The price is £139 per night from 25 Aug to 26 Aug
£139
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (205 reviews)
"Perfect place to stay the night. You can hear the train passing by, but there are ear plugs and a white noise machine in the room. It didn't bother us at all, but it might other folks"

Reviewed on 29 Jun 2026

Station Inn Pawling
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is £91 per night from 2 Aug to 3 Aug
£91
2 Aug - 3 Aug
includes taxes & fees
8/10 Very good! (1,332 reviews)
"I have stayed a couple times this year already and each time I've had a very relaxing stay. The staff have been helpful every time I needed Assistance or how to question. I stay on my own as a short relaxing getaway and found the bed to be very comfortable and the entire property very clean."

Reviewed on 25 Jul 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is £83 per night from 2 Aug to 3 Aug
£83
2 Aug - 3 Aug
includes taxes & fees
Best Western Danbury/Bethel
See all 848 properties in Pawling
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.
See properties

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.

Explore a world of travel with Expedia

* 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.