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.
Radio Hotel
Manhattan
Price was CA $2,056, price is now CA $1,255 per person
CA $1,255
per person
Jul 6 - Jul 11
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,511 reviews)
Great quiet room even with concerts at the facility. Staff awesome! Only odd thing was the opaque shower wall into the room as we were there with our young adult daughters. Perfect room for a couple!
Reviewed on May 18, 2026
2 bedroom luxury Empire State VIEW
Manhattan
Price was CA $7,124, price is now CA $3,980 per person
CA $3,980
per person
Jul 8 - Jul 12
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!
Reviewed on Mar 19, 2026
1 Hotel Brooklyn Bridge
Price was CA $5,599, price is now CA $3,260 per person
CA $3,260
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
Fabulous location right next to the ferry to Manhattan for a quick jump over to the Financial District. Nice area to wander around and grab a bite to eat. Views are insane. We went to the rooftop restaurant for the skyline views. Food was decent but atmosphere was the showstopper. Would stay again.
Reviewed on May 17, 2026
Pawling Hotel Deals
Station Inn Pawling
7 Memorial Avenue Pawling NY
The price is CA $231 per night from Jun 1 to Jun 2
CA $231
CA $261 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (197 reviews)
"The Station Inn was the perfect place to stay. We were going to a concert at Daryl’s house, and the inn was only a few minutes drive to the venue. Self entry was easy to both the property and our room. Room was immaculate, comfortable, and very spacious. Would highly recommend!"
Reviewed on May 11, 2026
Studio 6 Extended Stay Fishkill Route 9 NY
25 Merritt Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Jun 1 to Jun 2
CA $110
CA $127 total
Jun 1 - Jun 2
includes taxes & fees
6.6/10 (1,006 reviews)
"The desk clerk was rude and unaccommodating. She said that they were sold out and our reservation was not honored AT ALL, and she said it was "tough lyck". We had to scramble to find another hotel"
Reviewed on May 18, 2026
Best Western Danbury/Bethel
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from May 24 to May 25
CA $136
CA $157 total
May 24 - May 25
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"The staff, Eric, was incredibly rude to both myself and any guest I saw him interact with. They were without hot water when I arrived in the afternoon and there was still no hot water the next morning. I requested that they cancel the rest of my days and refund me for those days as I did not want ..."
Reviewed on May 17, 2026
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.
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.
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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.
