Pawling Vacations from $314

Book a Hotel + Flight or Car together to unlock savings

Photo by Marina Timo

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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $830, price is now $314 per person
$314
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
Great room and polite staff and excellent restaurant and location.

Reviewed on Nov 15, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was $761, price is now $348 per person
$348
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
17.6/10 Exceptional! (1,180 reviews)
The room was super nice

Reviewed on Nov 16, 2025

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $848, price is now $418 per person
$418
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (3,945 reviews)
Clean room, great location.

Reviewed on Nov 14, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,059, price is now $556 per person
$556
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
18.4/10 Exceptional! (3,350 reviews)
Clean room, friendly and helpful staff.

Reviewed on Nov 15, 2025

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,556, price is now $818 per person
$818
per person
Jan 29 - Feb 1
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
19.2/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pawling
View all trips

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 Dec 16 to Dec 17
$243 total
Dec 16 - Dec 17
Total with taxes and fees
9/10 Wonderful! (183 reviews)
We stayed here overnight so that we could hit up Daryl's House for dinner and a concert. The inn is very well maintained, the room was very comfortable and not clean but immaculate! One of the best we have stayed at in years. If we come back to the area will stay again.

Reviewed on Oct 28, 2025

Station Inn Pawling
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Nov 29 to Nov 30
$115 total
Nov 29 - Nov 30
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Easy che kin nice, newly refurbished rooms.

Reviewed on Nov 13, 2025

Hampton Inn & Suites Poughkeepsie
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
$179 nightly
The price is $206 total per night from Dec 14 to Dec 15
$206 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Great restaurant. Clean hotel. Kind staff. Great ambiance.

Reviewed on Nov 9, 2025

Hotel Zero Degrees Danbury
See all 817 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices from $314 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.

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.