Pawling Vacations from $255

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Your Pawling Vacation

Our vacation packages to Pawling give you countless opportunities to immerse yourself in new sights, sounds and flavors. 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 vacation is just a few clicks away with Expedia.

The Latest Pawling vacation packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
Staff was friendly. Room was clean.

Reviewed on Jul 12, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (803 reviews)
Nice stay. No frills. But if youre looking for a decently priced hotel in Manhattan this one works. Good neighborhood. Easy access to subway.

Reviewed on Jul 12, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.8/10 Good! (1,467 reviews)
Beautiful hotel . Clean friendly. The pool area is amazing. I highly recommend.

Reviewed on Jul 6, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New York (JFK)
8.4/10 Very Good! (531 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul 10, 2025

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Discover the most popular places to visit in Pawling

John Kane House

Find out about the history of Pawling with a stop at John Kane House. While in this trendy area, you can savor the top-notch restaurants.

John Kane House

Pawling Hotel Deals

Station Inn Pawling
Station Inn Pawling
3 out of 5
7 Memorial Avenue, Pawling, NY
$215 nightly
The price is $243 total per night from Aug 11 to Aug 12
$243 total
Aug 11 - Aug 12
Total includes taxes and fees
9/10 Wonderful! (172 reviews)
"Very clean."

Reviewed on Jul 4, 2025

Station Inn Pawling
Hotel Zero Degrees Danbury
Hotel Zero Degrees Danbury
4 out of 5
15 Milestone Road, Danbury, CT
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $196 total per night from Jul 31 to Aug 1
$196 total
Jul 31 - Aug 1
Total includes taxes and fees
9/10 Wonderful! (1,010 reviews)
"Clean hotel, nice aesthetic"

Reviewed on Jul 12, 2025

Hotel Zero Degrees Danbury
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
$88 nightly
The price is $101 total per night from Jul 28 to Jul 29
$101 total
Jul 28 - Jul 29
Total includes taxes and fees
8/10 Very Good! (1,006 reviews)
"It was a rainy dark night when I arrived but everything went perfect at the motel and as soon as I opened the door to my room it smelled fresh and was very clean"

Reviewed on Jul 9, 2025

Microtel Inn & Suites by Wyndham Bethel/Danbury
See all 836 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.

Find the Best Pawling Vacation Packages

Pawling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
2,300
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Stormville Airport Antique Show & Flea Market, Whaley Lake and John Kane House

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Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices from $255 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 vacation to Pawling costs.
What are the cheapest months to go to Pawling?
You're likely to find lower prices and better availability in February, March and December. Explore our cheap Pawling vacation packages and you could land some excellent off-season deals.
How many days is enough for Pawling?
With a well-organized schedule, you can easily tick off the most popular Pawling sights in a few days. But if you prefer to explore off the beaten track or go on day trips, consider booking your Pawling vacation for longer.
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 vacation package well in advance.
Is it cheaper to book a Pawling vacation as a package?
Expedia vacation 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 customized Pawling vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Pawling?
If you're considering a spontaneous Pawling vacation, 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.
Does Expedia offer Book Now, Pay Later Pawling vacation packages?
Jet off on your dream getaway to Pawling with Expedia's Book Now, Pay Later vacations. No need to save up or wait until the next payday --- we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.