Dutchess County Vacations & Trips from $290
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Your Dutchess County Vacation
Choose a vacation package to Dutchess County and make planning your adventure easy. With the logistics arranged before you leave, you can focus on enjoying every minute in this exciting destination. With so much to see on a trip to Dutchess County, it can be hard to know where to begin. Kick off your journey in Poughkeepsie at Vanderbilt Mansion National Historic Site and Hyde Park Station — two much-loved attractions here. Another great city worthy of a spot on your itinerary is Pawling. Be sure not to miss Candlewood Lake and Stormville Airport Antique Show & Flea Market. Find some travel buddies and start packing, because your Dutchess County vacation is only clicks away with Expedia.
Top destinations in Dutchess County
Poughkeepsie
The Latest Dutchess County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
Manhattan
Save 100% on your flight
Price was $581, price is now $290 per person
$290
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
The elevator system is awful so pack your patience as you will be waiting about 10 minutes every time you need to use it.
Reviewed on Dec 6, 2025
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was $975, price is now $511 per person
$511
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (2,790 reviews)
Great hotel , will definitely be back!
Reviewed on Dec 6, 2025
The Inn At Fox Hollow Hotel
Price was $875, price is now $471 per person
$471
per person
Feb 27 - Mar 3
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
I stay here often and the rooms are spacious clean and the hotel staff is very accommodating. I always have a wonderful experience and I highly recommend staying here. They also offer free breakfast and dinner which is a nice perk.
Reviewed on Nov 25, 2025
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was $822, price is now $457 per person
$457
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (3,348 reviews)
Clean room, friendly staff, perfect location.
Reviewed on Dec 7, 2025
Find the Best Dutchess County Vacation Packages
Dutchess County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Top Sights | Innisfree Garden, Harlem Valley Rail Trail and Fishkill Ridge |
Dutchess County Hotel Deals
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Dec 14 to Dec 15
$108 total
Dec 14 - Dec 15
Total with taxes and fees
7.6/10 Good! (497 reviews)
Room was clean. Staff was kind. Good complimentary breakfast
Reviewed on Nov 23, 2025
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Dec 19 to Dec 20
$115 total
Dec 19 - Dec 20
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
Miguel is the best!! This is our 4th stay and he is always so professional, greets us with a smile and us very efficient at his job!
Reviewed on Dec 5, 2025
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $117 total per night from Dec 10 to Dec 11
$117 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (1,021 reviews)
Lovely property, wonderful staff will definitely return back.
Reviewed on Dec 2, 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.
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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.