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.
Caldwell House Bed & Breakfast
Price was CA $2,012, price is now CA $1,819 per person
CA $1,819
per person
Apr 25 - May 1
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9/10 Wonderful! (474 reviews)
Great place to stay. Wonderful breakfasts. Gracious and warm hospitality.
Reviewed on May 28, 2024
Sleep Inn & Suites Monroe - Woodbury
Price was CA $672, price is now CA $608 per person
CA $608
per person
Apr 2 - Apr 5
found 9 hours ago
Roundtrip flight included
Buffalo (BUF) to Newburgh (SWF)
9.4/10 Exceptional! (1,004 reviews)
We had a very nice stay. The room was so clean. The staff was
Reviewed on Feb 2, 2026
Holiday Inn Express & Suites Montgomery by IHG
Price was CA $921, price is now CA $864 per person
CA $864
per person
May 1 - May 5
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.8/10 Excellent! (786 reviews)
Very clean and generously sized room. Staff was very courteous and helpful
Reviewed on Jan 21, 2026
Wildflower Farms, Auberge Collection
Price was CA $5,472, price is now CA $5,433 per person
CA $5,433
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (54 reviews)
Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect
Reviewed on Dec 13, 2025
Pleasant Valley Hotel Deals
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Feb 16 to Feb 17
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
Residence Inn by Marriott Kingston
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Mar 1 to Mar 2
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
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Feb 21 to Feb 22
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
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.
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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.
