Title: Pleasant Valley Vacation Packages & Trips 2026 from CA $487 | Expedia.ca [Hotels in Pleasant Valley](https://expedia.ca/Pleasant-Valley-Hotels.d6046250.Travel-Guide-Hotels)[Vacation Rentals in Pleasant Valley](https://expedia.ca/Pleasant-Valley-Vacation-Rentals.d6046250.Travel-Guide-VacationRentals)[Things to do in Pleasant Valley](https://expedia.ca/Things-To-Do-In-Pleasant-Valley.d6046250.Travel-Guide-Activities)[Pleasant Valley Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Valley.d6046250.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248621559866380/26ee89c3-a965-4de6-9e9f-a8e12db702c1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pleasant Valley Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by louann ohora - ## 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 Pleasant Valley Vacation The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like [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 [Culinary Institute of America](https://www.expedia.ca/Culinary-Institute-Of-America-Hyde-Park.d6093745.Vacation-Attraction). Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia. ## Top Pleasant Valley Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/1b0779e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Middletown - Goshen CA $487 per person Feb 13 - Feb 15 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.6/10 Excellent! (1,002 reviews) The stay was excellent. The pool was a perfect temp for all to unwind after a long drive. We enjoyed the breakfast. The staff was very friendly and helpful. Reviewed on Dec 2, 2025 ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Newburgh Stewart Airport CA $545 per person Jan 23 - Jan 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newburgh (SWF) 8.2/10 Very Good! (691 reviews) Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained. Reviewed on Oct 30, 2025 ![Holiday Inn Express & Suites Middletown - Goshen by IHG](https://images.trvl-media.com/lodging/42000000/41530000/41524600/41524586/697f516f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Middletown - Goshen by IHG CA $826 per person Feb 6 - Feb 9 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.8/10 Excellent! (695 reviews) Great property right off the highway. Clean comfortable rooms, free breakfast that was pretty good. Nice staff at check-in. Tons of parking and a great basic hotel Reviewed on Oct 13, 2025 ![Holiday Inn Express Hotel & Suites Chester by IHG](https://images.trvl-media.com/lodging/2000000/1200000/1194400/1194365/02f3df9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Chester by IHG CA $712 per person Feb 6 - Feb 9 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.4/10 Very Good! (1,003 reviews) The breakfast was a hit, the place is clean and I would stay here again. Reviewed on Dec 14, 2025 ![Holiday Inn Express & Suites Montgomery by IHG](https://images.trvl-media.com/lodging/8000000/7820000/7814700/7814618/98944f60_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Montgomery by IHG CA $605 per person Feb 6 - Feb 9 found 16 hours ago Roundtrip flight included Toronto (YYZ) to Newburgh (SWF) 8.8/10 Excellent! (786 reviews) When checking in I asked about the pool, was not told until day 6 that they were waiting on parts to heat the pool and pool room. Needless to say, my grandchildren attempted to swim in cold water and the pool room was cold. Not very good customer service at the front desk. Then upon checkout, there was no notice in my account about a cash deposit to be returned and I had forgotten about it until 3 hours into our trip home to Georgia. When I called and asked about it the GM wasn't available until Monday. When she called me back she wanted to put cash in the mail, and said that I had to pay for the shipping on it and was very nasty to me as if it were my own fault because I used cash and forgot about it. Reviewed on Dec 5, 2025 ## Ready to book your vacation to Pleasant Valley? Choose your dates ## Pleasant Valley Hotel Deals ![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 $126 CA $146 total Dec 26 - Dec 27 includes taxes & fees 8.8/10 Excellent! (1,007 reviews) Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back. Reviewed on Dec 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F12%2F2025&endDate=27%2F12%2F2025&selected=1927088&PinnedHotelID=1927088&HadPinnedHotel=true®ionId=6046250) ![Quality Inn Poughkeepsie](https://images.trvl-media.com/lodging/1000000/10000/6500/6465/a647c710_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Poughkeepsie 536 Haight Ave, Building A Poughkeepsie NY Fully refundableReserve now, pay when you stay CA $128 CA $148 total Dec 23 - Dec 24 includes taxes & fees 7.6/10 Good! (498 reviews) Room was clean. Staff was kind. Good complimentary breakfast Reviewed on Nov 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F12%2F2025&endDate=24%2F12%2F2025&selected=6465&PinnedHotelID=6465&HadPinnedHotel=true®ionId=6046250) ![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 $157 CA $176 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.8/10 Excellent! (790 reviews) Everything was great. Fantastic breakfast. Fire alarm went off the first night we were there and we had to wait till that was over but other than that everything was good Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=15715238&PinnedHotelID=15715238&HadPinnedHotel=true®ionId=6046250) [See all 1,116 properties in Pleasant Valley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=6046250) 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) ### What to do in Pleasant Valley ![Llama/Alpaca Hike and Farm Tour](https://mediaim.expedia.com/localexpert/3516519/efb72c7c-dbcc-4530-a54f-bf934f0d9971.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Llama/Alpaca Hike and Farm Tour CA $92 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/llamaalpaca-hike-and-farm-tour.a3516519.activity-details) [See all activities in Pleasant Valley](https://expedia.ca/things-to-do/search?rid=6046250) ## 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