
Pleasant Valley Vacation Packages
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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, Vassar College and Culinary Institute of America. 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.

The Crossroads Hotel, Newburgh
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
7.4/10 Good! (492 reviews)
Good value property. Room was updated and very comfortable. Staff was very friendly and helpful. Hallways and other common areas could use some refreshing. Would stay again.
Reviewed on Aug. 6, 2025



Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,012 reviews)
Every time I stay at the Red roof Inn, I am never disappointed. It is an excellent hotel that is safe, clean, and the staff is fabulous.
I highly recommend it.
Reviewed on Aug. 6, 2025

Hampton Inn & Suites Newburgh Stewart Airport
per person
Oct 9 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
9.2/10 Wonderful! (924 reviews)
The Hotel its self was nice and clean. Staff was okay, not overly welcoming. The area that we were in was not the best and that was coming from a Sheriff we had met at the hotel. Area has high drugs and crime. We actually saw someone being arrested for theft at the gas station down the street. We were there just for an overnight so it was okay.
Reviewed on Aug. 6, 2025
Pleasant Valley Hotel Deals

The Crossroads Hotel, Newburgh
5 Lakeside Rd, Newburgh, NY
The price is CA $117 per night from Sep 7 to Sep 8
CA $117
CA $139 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (501 reviews)
"Beds are comfortable with great bedding"
Reviewed on Aug. 5, 2025

Holiday Inn Express Poughkeepsie by IHG
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $174 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"
Reviewed on Aug. 3, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 1 to Sep 2
CA $221
CA $250 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (371 reviews)
"Loved this modern and clean hotel."
Reviewed on Aug. 1, 2025
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.
What to do in Pleasant Valley

Llama/Alpaca Hike and Farm Tour
CA $92
per adult
100% of travellers recommend
Frequently asked questions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.