Pawling Vacation Packages

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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.

Top Pawling Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Jul. 29 - Aug. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (438 reviews)
Not a lot for the price. Front staff was not super friendly. The standard room is very standard, small and very expensive. The location is not super convenient and on the busy road. Parking is tough but they do have valet. The view on the beach is beautiful and the people working the beach are were super nice. I think there are much better options and just didn't know the area well enough to find them. I know for next time.

Reviewed on Jun. 10, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug. 22 - Aug. 25
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (549 reviews)
Smart hotel superbly located

Reviewed on Jun. 12, 2024

RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 22 - Jul. 27
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (3,147 reviews)
I think this is one of the best options to stay at if you’re visiting NYC for the first time. It is a great location and is close to many things. It is also very close to a lot of subway stations and was easy to get to from the airport via the train. Staff were always very friendly and helpful. Breakfast was pretty good and never had to wait long to eat.

Reviewed on Jun. 17, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep. 13 - Sep. 16
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Great service-middle of action

Reviewed on Jun. 13, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Aug. 1 - Aug. 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
Lovely stay. Loved the vibe!

Reviewed on Jun. 14, 2024

Pawling Hotel Deals

Station Inn Pawling
Station Inn Pawling
3 out of 5
7 Memorial Avenue, Pawling, NY
The price is CA $315 per night from Jul. 2 to Jul. 3
CA $315
CA $353 total
includes taxes & fees
Jul 2 - Jul 3
9/10 Wonderful! (146 reviews)
"Lot of charm at the Sation Inn! And it located within very short walking distance to shops/restaruants/bar.. Great spot"

Reviewed on Jun. 13, 2024

Station Inn Pawling
Ethan Allen Hotel
Ethan Allen Hotel
3.5 out of 5
21 Lake Avenue Extension, I-84 at Exit 4, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jun. 25 to Jun. 26
CA $153
CA $176 total
includes taxes & fees
Jun 25 - Jun 26
7.8/10 Good! (1,004 reviews)
"Haven't been to Ethan Allen in years. I was in town on business. Still as I remember it. Great stay..!"

Reviewed on Jun. 13, 2024

Ethan Allen Hotel
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundable
The price is CA $196 per night from Jun. 19 to Jun. 20
CA $196
CA $220 total
includes taxes & fees
Jun 19 - Jun 20
8.6/10 Excellent! (1,005 reviews)
"They have a little bit of everything, including an indoor heated pool, a hot tub, laundry, a fitness center, and a full breakfast as opposed to those with a continental breakfast. The staff is very friendly, and the rooms as very comfortable."

Reviewed on Jun. 14, 2024

HYATT house Fishkill/Poughkeepsie
See all 824 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pawling vacation package cost?
From as little as CA $744. Yes, you read that correctly. Our Pawling vacation packages are a great way to stretch your budget. Combine your hotels, flights and car rentals and get to know this popular destination.
How do I get a cheap travel package to Pawling?
You’ll save a pile of money if you bundle your flights, hotels and car rentals into a Pawling vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels all over the world, so you’ll always have plenty of variety to choose from. Want to save even more? Add some interesting activities to your package deal and unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Pawling?
Pawling boasts numerous interesting places to discover, like John Kane House. Spend your nights in a hotel close by and make sightseeing simple.
What are the top hotels in Pawling?
Station Inn Pawling is one of Pawling’s leading hotels. Book a room here and you can snooze soundly knowing you’re in good hands.
How far in advance should I book my Pawling vacation?
It all depends on the airline, but it’s usually possible to compare international airfares on Expedia nearly a year in advance. While it’s generally a good idea to book ahead of time, lucky travelers occasionally nab a cheaper seat just weeks before the date of departure.
What does an Expedia Pawling travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your perfect Pawling travel package. Once you’ve made your booking, you can add on the fun things like tours and activities. Don’t forget — the more you bundle, the more discounts you’ll get!
What should I know before booking a Pawling travel package?
Bundling your bookings into a Pawling vacation package is the most convenient way to organize your trip. Not only that, you’ll save when you combine your hotels, flights and car rentals. Once you’ve booked, why not add on a day tour or an activity?
Can I choose my airline with a Pawling Expedia vacation package?
Yes, and with over 550 airlines to pick from across the globe, it’s all about choice. Have a look through the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Pawling vacation package?
It’s difficult to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Pawling vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Discover the most popular places to visit in Pawling

Image for John Kane House

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
Image for Akin Free Library

Akin Free Library

Akin Free Library is just one of the places to see in Pawling, so why not enjoy the other things to explore during your travels?

Akin Free Library

Other vacations you might like

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