Pawling Vacations from $332

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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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $568, price is now $332 per person
$332
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
No microwave, ice bucket, coffee pot, or fridge unfortunately. Our tv remote didn’t work either so we couldn’t watch a lot of tv

Reviewed on Jan 27, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $737, price is now $348 per person
$348
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,685, price is now $1,394 per person
$1,394
per person
Apr 5 - Apr 10
found 22 hours ago
Roundtrip flight included
Los Angeles (QLA) to New Haven (HVN)
No reviews
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $1,492, price is now $818 per person
$818
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,790 reviews)
The staff was super friendly, everything was Super clean love the view

Reviewed on Jan 28, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,840, price is now $1,615 per person
$1,615
per person
Apr 10 - Apr 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
You need more dinner options in hotel

Reviewed on Jan 17, 2026

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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
$181 nightly
The price is $205 total per night from Feb 28 to Mar 1
$205 total
Feb 28 - Mar 1
Total with taxes and fees
9/10 Wonderful! (188 reviews)
We’ve stayed at Station Inn several times and have always enjoyed our stay. Very homey and convenient location.

Reviewed on Jan 22, 2026

Station Inn Pawling
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Feb 8 to Feb 9
$101 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Very good n clean

Reviewed on Jan 24, 2026

Courtyard by Marriott Poughkeepsie
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $179 total per night from Feb 23 to Feb 24
$179 total
Feb 23 - Feb 24
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Nice

Reviewed on Jan 20, 2026

Hotel Zero Degrees Danbury
See all 821 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 $332 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.