Title: Pawling Vacation Rentals from $126: Search Short-Term Rentals | Expedia.com [Pawling Travel Guide](https://expedia.com/Pawling.dx6278767)[Hotels in Pawling](https://expedia.com/Pawling-Hotels.d6278767.Travel-Guide-Hotels)[Flights to Pawling](https://expedia.com/Cheap-Flights-To-Pawling.d6278767.Travel-Guide-Flights)[Car Rentals in Pawling](https://expedia.com/Car-Rentals-In-Pawling.d6278767.Car-Rental-Guide)[Pawling Vacation Packages](https://expedia.com/Pawling.d6278767.Destination-Travel-Guides) ![Appalachian Trail](https://images.trvl-media.com/place/6278767/77ffe529-3d3e-49fe-8ae7-6cb44a357bf5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6278767/77ffe529-3d3e-49fe-8ae7-6cb44a357bf5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6278767&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6278767&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6278767&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=6278767&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pawling vacation rentals ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/fe9d9847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/15697af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/d25ce94c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94953800/94953757/e40d957c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dainty New Preston Cottage w/ Dock & Lake Views! [](https://www.expedia.com/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information) New Preston $449 nightly $517 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/New-Preston-Hotels-Dainty-New-Preston-Cottage-W-Dock-Lake-Views.h94953757.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-18&endDate=2026-04-19®ionId=6278767&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=VILLA) Chalets [](https://www.expedia.com/Hotel-Search?destination=Pawling%2C+New+York%2C+United+States+of+America®ionId=6278767&latLong=41.562038%2C-73.602631&adults=2&startDate=2026-07-03&d1=2026-07-03&endDate=2026-07-06&d2=2026-07-06&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPawling-Vacation-Rentals.d6278767.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPawling-Vacation-Rentals.d6278767.Travel-Guide-VacationRentals) ## Top Pawling Hotel Reviews ![Hyatt Place Poughkeepsie / Hudson Valley](https://images.trvl-media.com/lodging/38000000/37970000/37960500/37960419/9bb388bd_y.jpg) ### Hyatt Place Poughkeepsie / Hudson Valley 10/10 Excellent "Reception was great! Quick check-in and checkout. Thank you!" [](https://expedia.com/Poughkeepsie-Hotels-Hyatt-Place-Poughkeepsie.h37960419.Hotel-Information) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/875b6b8c_y.jpg) ### DoubleTree by Hilton Poughkeepsie Convention Center 2/10 Terrible "When I returned to my room, it was 80 degrees even though the thermostat was set to 68\. I went to the front desk and they sent maintenance. Maintenance told me there wasn't anything they could do because the air conditioning isn't working. He even showed me another room to show that it would be just as hot. Nobody should have to be stuck in a room this hot, especially when they're paying for the room and a ridiculous $600 dollar deposit on top of it. It's not even that the a/c doesn't work; they just don't have it on and refuse to turn it on. The staff didn’t offer any remedy, or do anything to help. They just simply handled it with a “There’s nothing we can do.” I stay here whenever I visit my brother, but from now on, I’ll be staying somewhere else. " [](https://expedia.com/Poughkeepsie-Hotels-Poughkeepsie-Grand-Hotel.h14563.Hotel-Information) ![Best Western Fishkill Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/12500/12443/847efacf_y.jpg) ### Best Western Fishkill Inn & Suites 10/10 Excellent "Loved the accommodations, not your typical hotel. Perfect for traveling with a dog." [](https://expedia.com/Fishkill-Hotels-Best-Western-Fishkill-Inn-Suites.h12443.Hotel-Information) ![Inn at Bellefield / Hyde Park, Residence Inn by Marriott](https://images.trvl-media.com/lodging/100000000/99860000/99850800/99850733/1ee75d40_y.jpg) ### Inn at Bellefield / Hyde Park, Residence Inn by Marriott 10/10 Excellent "Beautiful hotel with a vibrant lobby/restaurant/bar area. Rooms are spacious and well appointed. Hotel is very clean and staff is friendly. Can’t wait to return there! " [](https://expedia.com/Hyde-Park-Hotels-Inn-At-Bellefield-Hyde-Park.h99850733.Hotel-Information) ![Holiday Inn Express Fishkill-Mid Hudson Valley by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1680400/1680342/5b94363e_y.jpg) ### Holiday Inn Express Fishkill-Mid Hudson Valley by IHG 10/10 Excellent "The staff was very friendly and courteous. The room was Great! They provide "Dove" soaps and lotions. The bathroom floor was super slippery after you shower. The breakfast was nice. There was a nice variety. The juice machine wasnt working during our stay, but they had bottles of yummy chocolate milk. I was hoping for bacon as shown in one of the photos, its my favorite, but there was sausage, which was good too. The pool was nice. The jets in the hot tub were barely working. Overall, I'd deff stay there again." [](https://expedia.com/Poughkeepsie-Hotels-Holiday-Inn-Express-Fishkill-Mid-Hudson-Valley.h1680342.Hotel-Information) ![Hotel Zero Degrees Danbury](https://images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/8667a2b4_y.jpg) ### Hotel Zero Degrees Danbury 10/10 Excellent "Parking safe & close. Great restaurant inside the hotel." [](https://expedia.com/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information) ![Home2 Suites By Hilton Poughkeepsie](https://images.trvl-media.com/lodging/104000000/103400000/103394200/103394153/7472348e_y.jpg) ### Home2 Suites By Hilton Poughkeepsie 10/10 Excellent "How do you describe a hotel with all of the amenities you expect, but with the family like feel of a bnb....Home 2 Suites! From the moment I walked into the door, I felt welcomed. I was greeted with, Hey Glenda, I spoke with you earlier today. I'm glad you made it safely. Every staff member was courteous and welcoming. Every day I spoke with the General Manager, who was not hiding in the back office, but was front and center every day. I loved it. Every morning I was greeted by he and at least 2 members of his staff when I came downstairs to a hot ready to serve breakfast that varied each day. Every evening I was welcomed back to the property by a smiling front desk clerk. My grand children enjoyed the pool. Every day I promised myself that I would hit the gym. And every evening I enjoyed a spacious studio suite that was equipped with a microwave, refrigerator and sink. When I say that it was a thoroughly enjoying stay, I mean it. I would definitely stay at the Home 2 Suites in Poughkeepsie again. And I can't fail to mention that the Hilton site offered fantastic Flash sales on bookings that gave me a great price. And it was a convenient ride away from each of the 3 JW Bethel sites." [](https://expedia.com/Poughkeepsie-Hotels-Home2-Suites-By-Hilton-Poughkeepsie.h103394153.Hotel-Information) ![Ethan Allen Hotel](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/bb9d6c7e_y.jpg) ### Ethan Allen Hotel 8/10 Good "Breakfast was fresh, and the hotel was very well Kept." [](https://expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![HYATT house Fishkill/Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1340000/1336000/1335929/w3836h2558x4y3-858cbdd6_y.jpg) ### HYATT house Fishkill/Poughkeepsie 10/10 Excellent "My family and I had a 360° experience here the welcoming was genuine. The room was comfortable the amenities the cleanliness and the hospitality, hands down, generous. Filled with gratitude, wonderful experience. " [](https://expedia.com/Poughkeepsie-Hotels-HYATT-House-FishkillPoughkeepsie.h1335929.Hotel-Information) ## Find out more about Pawling **Everything you need to know about Pawling vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pawling vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Pawling vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Pawling. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pawling in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Pawling rentals** At Expedia, we put the best Pawling vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Pawling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pawling vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pawling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Pawling ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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