Title: Pawling Vacation Packages & Trips 2026 from CA $836 | 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/6278767/94e13aba-8a2e-4cf7-aa3e-3051ce7d8aec.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pawling Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan CA $836 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April. Reviewed on Feb 6, 2026 ![NobleDEN Hotel](https://images.trvl-media.com/lodging/9000000/8690000/8682300/8682234/cb1dc844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### NobleDEN Hotel Manhattan CA $1,915 per person Apr 2 - Apr 8 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.8/10 Exceptional! (1,411 reviews) Very clean and great staff! They were very accommodating! Reviewed on Feb 3, 2026 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/524d3c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan CA $2,010 per person Apr 25 - Apr 29 found 12 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby. Reviewed on Feb 2, 2026 ![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 $2,194 per person Apr 25 - Apr 29 found 12 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (159 reviews) Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping. Reviewed on Jan 3, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,469 per person Apr 25 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) The entire stay was exceptional! From the point of entry to departure 10/10 Reviewed on Jan 29, 2026 ## 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 $236 CA $267 total Mar 8 - Mar 9 includes taxes & fees 9/10 Wonderful! (188 reviews) We’ve stayed at Station Inn several times and have always enjoyed our stay. Very homey and convenient location. Reviewed on Jan 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=20155827&PinnedHotelID=20155827&HadPinnedHotel=true®ionId=6278767) ![Courtyard by Marriott Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6000/5910/990080f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott Poughkeepsie 2641 South Road/Route 9 Poughkeepsie NY Fully refundableReserve now, pay when you stay CA $144 CA $162 total Mar 1 - Mar 2 includes taxes & fees 8.8/10 Excellent! (1,008 reviews) Very friendly, kind staff and clean room Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=5910&PinnedHotelID=5910&HadPinnedHotel=true®ionId=6278767) ![Best Western Danbury/Bethel](https://images.trvl-media.com/lodging/1000000/10000/4900/4841/b09513bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Danbury/Bethel 11 Stony Hill Road Bethel CT Fully refundableReserve now, pay when you stay CA $101 CA $116 total Feb 11 - Feb 12 includes taxes & fees 7.6/10 Good! (1,002 reviews) Clean rooms, hotel could use some updates. Reviewed on Jan 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=4841&PinnedHotelID=4841&HadPinnedHotel=true®ionId=6278767) [See all 823 properties in Pawling](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®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