Pawling Vacations from $402

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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.
Holiday Inn Express & Suites Bronx - Barnabas area by IHG

Holiday Inn Express & Suites Bronx - Barnabas area by IHG

2.5 out of 5
Price was $653, price is now $402 per person
$402
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (1,053 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $2,323, price is now $1,311 per person
$1,311
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was $2,777, price is now $1,605 per person
$1,605
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)
Very clean, attentive staff and very helpful

Reviewed on Nov 8, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,082, price is now $635 per person
$635
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,547, price is now $1,510 per person
$1,510
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)

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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

Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
$138 nightly
The price is $156 total per night from Dec 10 to Dec 11
$156 total
Dec 10 - Dec 11
Total with taxes and fees
9.2/10 Wonderful! (217 reviews)
"Tidy small inn and very comfortable. Coffee and tea were available at a station in the hall as well as in each room. Easy to come and go. Small restaurants and coffee shop are within easy walking distance."

Reviewed on Oct 31, 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
$91 nightly
The price is $105 total per night from Dec 6 to Dec 7
$105 total
Dec 6 - Dec 7
Total with taxes and fees
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
$97 nightly
The price is $111 total per night from Nov 15 to Nov 16
$111 total
Nov 15 - Nov 16
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
"Clean place. Good location. Convenient shopping."

Reviewed on Nov 10, 2026

Best Western Danbury/Bethel
See all 852 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 $402 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.