Title: Poughkeepsie Waterfront Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $664 Expedia.ca [Hotels in Poughkeepsie Waterfront](https://expedia.ca/Poughkeepsie-Waterfront-Poughkeepsie-Hotels.0-n6338910-0.Travel-Guide-Filter-Hotels)[Flights to Poughkeepsie](https://expedia.ca/Cheap-Flights-To-Poughkeepsie.d6056317.Travel-Guide-Flights)[Things to do in Poughkeepsie](https://expedia.ca/Things-To-Do-In-Poughkeepsie.d6056317.Travel-Guide-Activities)[Poughkeepsie Waterfront Car Rentals](https://expedia.ca/Car-Rentals-In-Poughkeepsie-Waterfront.d6338910.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6093747/4b1a6750-92e5-4848-a246-4eb589961272.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Poughkeepsie Waterfront 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 Poughkeepsie Waterfront Vacation When you book a vacation package to Poughkeepsie Waterfront, you can relax and enjoy your escape knowing that all your travel plans have been worked out ahead of time. Uncover the many charms of this city while staying in a neighborhood like Arlington, which is great for culture. [Marist College](https://www.expedia.ca/Marist-College-Poughkeepsie.d6158002.Vacation-Attraction), [Vassar College](https://www.expedia.ca/Vassar-College-Poughkeepsie.d6085394.Vacation-Attraction) and [Franklin D. Roosevelt Presidential Library and Museum](https://www.expedia.ca/Franklin-D-Roosevelt-Presidential-Library-And-Museum-Hyde-Park.d6127069.Vacation-Attraction) are just a few of the many sights worth visiting during your trip to Poughkeepsie Waterfront. A couple of clicks is all it takes to create your dream Poughkeepsie Waterfront vacation on Expedia. ## Top Holiday Package Deals in Poughkeepsie Waterfront Price found within the past 48 hours. Click for updated prices. ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Yonkers Northwest Yonkers CA $664 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 8.2/10 Very Good! (1,621 reviews) Partially friendly and professional staff. Rooms are subpar because carpets are worn and not steam cleaned properly. Had to change my room due to nasty stench. The other half of staff during the daytime hours have a “NY do it yourself” attitude. Reviewed on Feb 5, 2026 ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn White Plains/Tarrytown CA $670 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 8/10 Very Good! (1,264 reviews) It was fine. Rooms were in ok condition; a bit older and need some remodelling. Staff was fine. Place needs a bit of a glow up. Reviewed on Feb 2, 2026 ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Tarrytown House Estate CA $750 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 8/10 Very Good! (1,001 reviews) Unique place, very clean and well Maintained. Reviewed on Feb 5, 2026 ![Sleepy Hollow Hotel](https://images.trvl-media.com/lodging/1000000/10000/4000/3956/ee0f5c7a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleepy Hollow Hotel CA $828 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 6.8/10 (1,002 reviews) Clean rooms and friendly staff Reviewed on Jan 13, 2026 ## Where to stay in Poughkeepsie Waterfront Find the best Poughkeepsie Waterfront areas and neighborhoods for the activities you enjoy most. [Learn more about Poughkeepsie Waterfront](https://expedia.ca/Poughkeepsie-Waterfront.dx6338910) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Arlington 1 out of top 10 points of interest in this area You'll enjoy the coffeehouses and art galleries in Arlington. You might want to make time for a stop at Frances Lehman Loeb Art Center or Vassar Golf Course. [Find hotel + flight trips in Arlington](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Arlington&DestID=553248634999048383&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![view of the mid hudson bridge to poughkeepsie, new york from highland (suspension bridge over river crossing) scenic landmark](https://images.trvl-media.com/place/553248634999249867/f2c24c28-5e70-4413-8013-f4424bebc55d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Crown Heights Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop. [Find hotel + flight trips in Crown Heights](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Crown%20Heights&DestID=553248634999249867&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Poughkeepsie Journal Building - New York](https://images.trvl-media.com/place/944697092109320192/28bf0e70-d274-45f1-b83f-0dad2ad39a5f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Poughkeepsie 2 out of top 10 points of interest in this area If you're spending some time in Downtown Poughkeepsie, Bardavon 1869 Opera House and Mid-Hudson Civic Center are top sights worth seeing. [Find hotel + flight trips in Downtown Poughkeepsie](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Poughkeepsie&DestID=944697092109320192&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![panoramic view of mid hudson bridge over hudson river valley](https://images.trvl-media.com/place/553248634998900489/43dfaefc-f04f-45b7-bc35-40574f714c7b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Red Oaks Mill The river views, waterfalls, and breweries are just a few things travelers enjoy about Red Oaks Mill. If you want to experience more of the area, check out Locust Grove or Poughkeepsie Galleria. [Find hotel + flight trips in Red Oaks Mill](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Red%20Oaks%20Mill&DestID=553248634998900489&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![view of the mid hudson bridge to poughkeepsie, new york from highland (suspension bridge over river crossing) scenic landmark](https://images.trvl-media.com/place/907719581714612224/db4be363-892f-4ee6-b91a-2759dffb4f70.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Union Street Historic District When in Union Street Historic District, you can plan a visit to Mid-Hudson Civic Center and Bardavon 1869 Opera House, some noteworthy sights in the nearby area. [Find hotel + flight trips in Union Street Historic District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Union%20Street%20Historic%20District&DestID=907719581714612224&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Poughkeepsie Waterfront Hotel Deals ![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 Feb 16 - Feb 17 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=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=5910&PinnedHotelID=5910&HadPinnedHotel=true®ionId=6338910) ![Residence Inn by Marriott Kingston](https://images.trvl-media.com/lodging/16000000/15720000/15715300/15715238/3f674783_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Residence Inn by Marriott Kingston 800 Frank Sottile Boulevard Kingston NY Fully refundableReserve now, pay when you stay CA $168 CA $188 total Mar 1 - Mar 2 includes taxes & fees 8.8/10 Excellent! (833 reviews) Have stayed here many times. they have done a really good job of keeping the property up to date. Very nice people. Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=15715238&PinnedHotelID=15715238&HadPinnedHotel=true®ionId=6338910) ![DoubleTree by Hilton Poughkeepsie Convention Center](https://images.trvl-media.com/lodging/1000000/20000/14600/14563/acc87956_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Poughkeepsie Convention Center 40 Civic Center Plz Poughkeepsie NY Fully refundableReserve now, pay when you stay CA $139 CA $163 total Feb 21 - Feb 22 includes taxes & fees 8.4/10 Very Good! (1,004 reviews) Room was clean and comfortable. Staff was so friendly. Would definitely stay here again Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=14563&PinnedHotelID=14563&HadPinnedHotel=true®ionId=6338910) [See all 972 properties in Poughkeepsie Waterfront](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=6338910) 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) ## Frequently asked questions ### How much does a Poughkeepsie Waterfront vacation package cost? ### What are the cheapest months to go to Poughkeepsie Waterfront? ### How many days is enough for Poughkeepsie Waterfront? ### How to find the best Poughkeepsie Waterfront package deals? ### Is it cheaper to book a Poughkeepsie Waterfront vacation as a package? ### When to book a vacation package to Poughkeepsie Waterfront? ### How to plan a trip to Poughkeepsie Waterfront? > 1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Poughkeepsie Waterfront. > 2. Set your budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Poughkeepsie Waterfront. Then, pick a hotel that suits your budget, whether that's a wallet-friendly option or a more upscale getaway. > 3. Determine how many days away: Start by listing all the activities and sights you want to get to in Poughkeepsie Waterfront. Then, estimate how long you'll need at each, including any travel time. > 4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Poughkeepsie Waterfront vacation package. ### Discover the most popular places to visit in Poughkeepsie Waterfront ![Springwood Estate - FDR Home](https://images.trvl-media.com/place/6156532/478bf03e-7c48-4738-a32e-08c4f77cf315.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Eleanor Roosevelt National Historic Site You can find out about the history of Haviland with a stop at Eleanor Roosevelt National Historic Site. While you're in the area, stroll along the riverfront. [](https://expedia.ca/Eleanor-Roosevelt-National-Historic-Site-Poughkeepsie.d6156532.Vacation-Attraction) ### Things to do ![Bear Mountain State Park+ BeaconTown 1-Day Tour From NY](https://mediaim.expedia.com/localexpert/50302489/1ceb0837-f410-471c-80a4-908b6cbc0dd2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bear Mountain State Park+ BeaconTown 1-Day Tour From NY CA $128 per adult [](https://expedia.ca/things-to-do/bear-mountain-state-park-beacontown-1-day-tour-from-ny.a50302489.activity-details) [See all activities in Poughkeepsie](https://expedia.ca/things-to-do/search?rid=6338910) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.