Pawling Holidays from £1,092

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

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 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 23 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on 6 Aug 2025

La Quinta Inn & Suites by Wyndham Times Square South

La Quinta Inn & Suites by Wyndham Times Square South

3 out of 5
Manhattan
per person
20 Oct - 24 Oct
found 22 hours ago
Return direct flight included
Manchester (MAN) to New York (JFK)
9/10 Wonderful! (1,010 reviews)
Clean. Good location to where I needed to be.

Reviewed on 28 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
17 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on 3 Aug 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
11 Oct - 18 Oct
just found
Return direct flight included
Dublin (DUB) to New York (JFK)
7.8/10 Good! (1,511 reviews)
We loved the location. What we didn’t like was that there was no refrigerator or microwave in the room. There was also a fight in the room next door to ours and no one checked in to see if we were okay.

Reviewed on 5 Aug 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
9 Sept - 13 Sept
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,009 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

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 £193 per night from 7 Aug to 8 Aug
£193
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (174 reviews)
"Very clean."

Reviewed on 4 Jul 2025

Station Inn Pawling
Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

2 out of 5
80 Benedict Rd, Bethel, CT
Fully refundableReserve now, pay when you stay
The price is £72 per night from 12 Aug to 13 Aug
£72
12 Aug - 13 Aug
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"Great place to rest our head as we passed through!"

Reviewed on 4 Aug 2025

Microtel Inn & Suites by Wyndham Bethel/Danbury
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is £81 per night from 24 Aug to 25 Aug
£81
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"The hotel is an older one but still nice. The staff was so helpful and very nice. We chose the hotel for its outdoor pool area. The pool could use new lounge chairs, the ones there are dry rotting and not sturdy. The rooms were useable but a little outdated. We did switch our room because the first ..."

Reviewed on 3 Aug 2025

La Quinta Inn & Suites by Wyndham Danbury
See all 842 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

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.

* 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.