Title: Pawling Vacation Packages & Trips 2025/2026 from CA $798 | Expedia.ca [Hotels in Pawling](https://expedia.ca/Pawling-Hotels.d6278767.Travel-Guide-Hotels)[Vacation Rentals in Pawling](https://expedia.ca/Pawling-Vacation-Rentals.d6278767.Travel-Guide-VacationRentals)[Pawling Car Rentals](https://expedia.ca/Car-Rentals-In-Pawling.d6278767.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6278767/97433f45-2833-408f-beab-348accb22a5a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pawling Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Marina Timo - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Thunder-Ridge-Ski-Resort-Patterson.d6087207.Vacation-Attraction), [Whaley Lake](https://www.expedia.ca/Whaley-Lake-Holmes.d553248621555565637.Vacation-Attraction) and [Lake Dutchess](https://www.expedia.ca/Lake-Dutchess-Holmes.d553248635976197011.Vacation-Attraction) 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. ![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/8c07d74e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza New York Times Square Manhattan CA $798 per person Jan 2 - Jan 5 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (2,748 reviews) great experience overall Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-05/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11677770&paandie=true&dealMarker=Z3FOz0qxgeQ51dAKnqeRVorc03sfaMFeSbUoJHPHiMhcbVzwUHv0mYpmKenmE8Kb) ![Hyatt Regency Jersey City on the Hudson](https://images.trvl-media.com/lodging/1000000/890000/880300/880227/6f887cd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Jersey City on the Hudson Downtown Jersey City CA $961 per person Dec 31 - Jan 4 found 13 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.4/10 Very Good! (1,546 reviews) Didnt have breakfast food below average for a hyatt. Not very attractive or alluring. PARKING IS 52/DAY GET READY FOR THAT NONSENSE. NEVER AGAIN Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-04/?FromAirport=YTO&Destination=EWR&NumRoom=1&NumAdult=2&NumChild=0&hotelId=880227&paandie=true&dealMarker=pqldusvS2tnKqL6Byxfl1seacI5QX_R-faYngDWumlPjDJ8cWvp48qBUAwLxro-x) ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $1,469 per person Jan 2 - Jan 5 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.6/10 Exceptional! (151 reviews) A perfect place to stay!! Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-02/2026-01-05/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=96472655&paandie=true&dealMarker=Z3FOz0qxgeQ51dAKnqeRViP0Z6SJp5KMBxbcH1eENDNS1AlBFZFuHXZ_EoRmDqiz) ![JW Marriott Essex House New York](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/04695212_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Essex House New York Manhattan CA $1,283 per person Jan 5 - Jan 9 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (NYC) 8.8/10 Excellent! (1,002 reviews) Great location clean rooms your site should offer park views we had a view of the building across the street Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-05/2026-01-09/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534143&paandie=true&dealMarker=OVOzQV3ckHcuIFVneYzVPYiQfdxYd8K0gVAkmNkAQxY4IEDPgxQo13_CaaTm8GcB) ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan CA $860 per person Jan 14 - Jan 18 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (3,359 reviews) Riu Plaza Manhattan was the perfect location and exceeded expectations.. Room was very quiet,no street noise! Staff was very helpful. My fourth stay at this hotel,never disappoints. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-14/2026-01-18/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=60677495&paandie=true&dealMarker=Z3FOz0qxgeQ51dAKnqeRVsG5b91H3WF-U0LxiqLGi0XFnFB3QEBD5trPTSi5yQz8) ## Ready to book your vacation to Pawling? Choose your dates ## Pawling Hotel Deals ![Station Inn Pawling](https://images.trvl-media.com/lodging/21000000/20160000/20155900/20155827/b2f9fdde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Station Inn Pawling 7 Memorial Avenue, Pawling, NY CA $313 CA $354 total Nov 30 - Dec 1 includes taxes & fees 9/10 Wonderful! (180 reviews) We stayed here overnight so that we could hit up Daryl's House for dinner and a concert. The inn is very well maintained, the room was very comfortable and not clean but immaculate! One of the best we have stayed at in years. If we come back to the area will stay again. Reviewed on Oct 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F11%2F2025&endDate=01%2F12%2F2025&selected=20155827&PinnedHotelID=20155827&HadPinnedHotel=true®ionId=6278767) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/47fa2e85_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Poughkeepsie 2361 South Rd, Poughkeepsie, NY Fully refundableReserve now, pay when you stay CA $142 CA $165 total Nov 29 - Nov 30 includes taxes & fees 8.6/10 Excellent! (1,013 reviews) We had some issues with ants in the room, around the coffee bar. We reported it and were quickly given another room. Staff was helpful and friendly. Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F11%2F2025&endDate=30%2F11%2F2025&selected=1927088&PinnedHotelID=1927088&HadPinnedHotel=true®ionId=6278767) ![Microtel Inn & Suites by Wyndham Bethel/Danbury](https://images.trvl-media.com/lodging/1000000/580000/579300/579216/ef7dd368_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Microtel Inn & Suites by Wyndham Bethel/Danbury 80 Benedict Rd, Bethel, CT Fully refundableReserve now, pay when you stay CA $124 CA $143 total Nov 2 - Nov 3 includes taxes & fees 8/10 Very Good! (1,027 reviews) Comfortable bed Reviewed on Oct 22, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=579216&PinnedHotelID=579216&HadPinnedHotel=true®ionId=6278767) [See all 820 properties in Pawling](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F10%2F2025&endDate=01%2F11%2F2025®ionId=6278767) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/John-Kane-House-Pawling.d6258690.Vacation-Attraction) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)