Pawling Vacations from ￥336,211

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The Latest Pawling Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥530,007, price is now ￥336,211 per person
￥336,211
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
This property is in the perfect location to see all the sights in NYC! The room was excellent, with a side view of Times Square and the breakfast was the perfect start to each day! I would definitely recommend and go back!

Reviewed on Jul 29, 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥875,094, price is now ￥535,713 per person
￥535,713
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (719 reviews)

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was ￥496,890, price is now ￥357,028 per person
￥357,028
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,834 reviews)

EVEN Hotel Brooklyn by IHG

EVEN Hotel Brooklyn by IHG

4 out of 5
Price was ￥493,794, price is now ￥361,981 per person
￥361,981
per person
Oct 16 - Oct 23
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,947 reviews)

Freehand New York

Freehand New York

4 out of 5
Manhattan
Price was ￥552,902, price is now ￥405,306 per person
￥405,306
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.6/10 Excellent! (2,058 reviews)
Magnifique mais manque quelques ressources spécifiques comme un ouvre bouteille à amener en chambre ainsi que sceau et glace…mais malgré tout personnel très à l’écoute et offre un bon service.

Reviewed on Jul 28, 2026

Find the Best Pawling Vacation Packages

Pawling Hotel Deals

Station Inn Pawling

Station Inn Pawling

3 out of 5
7 Memorial Avenue Pawling NY
The price is ￥27,035 per night from Aug 27 to Aug 28
￥27,035
￥30,583 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (205 reviews)
"Perfect place to stay the night. You can hear the train passing by, but there are ear plugs and a white noise machine in the room. It didn't bother us at all, but it might other folks"

Reviewed on Jun 29, 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
The price is ￥17,121 per night from Aug 2 to Aug 3
￥17,121
￥19,689 total
Aug 2 - Aug 3
includes taxes & fees
8/10 Very Good! (1,346 reviews)
"The bar was not open although it was a Monday evening. The breakfast was good and the staff at the front was very nice at check in."

Reviewed on Jul 28, 2026

Ethan Allen Hotel
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is ￥17,548 per night from Aug 4 to Aug 5
￥17,548
￥20,377 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"The room was clean and comfortable. The grounds were well maintained. The staff was friendly and helpful. Although, when we checked in, we were sent to a room that was yet to be cleaned. We had to come back down and informed them and was then given a room that was ready. My family and I had to take ..."

Reviewed on Jul 28, 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 840 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.

Stay near popular Pawling attractions

Daryl's House Club

You can make plans for a show at Daryl's House Club during your trip to Pawling.
See properties

Frequently asked questions

How much does a Pawling vacation package cost?
You'll find cheap prices from ￥336,211 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?
Plan your getaway for the off-season and you're likely to score cheap Pawling vacation packages. Bear in mind that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Pawling?
Generally, a handful of days is enough to tick off the major sights during your Pawling vacation. But if you'd like to have some time to unwind or take day tours, think about extending your trip.
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.
How to plan a trip to Pawling?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the type of activities available will also help you decide when to visit Pawling.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Pawling.
  3. Work out your trip length: Consider how much time you want to spend exploring Pawling. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the perfect Pawling vacation package for you.

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