Dutchess County Vacations & Trips from $637
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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
Beacon
The Latest Dutchess County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad
Manhattan
Price was $1,608, price is now $637 per person
$637
per person
Mar 8 - Mar 15
found 16 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff was really nice, rooms were clean will definitely be staying here again
Reviewed on Jan 4, 2026
Courtyard New York Manhattan/ Midtown East
Manhattan
Price was $2,033, price is now $973 per person
$973
per person
Mar 11 - Mar 16
found 15 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Room was very clean, staff were extremely helpful and polite.
Reviewed on Jan 4, 2026
Sheraton New York Times Square Hotel
Manhattan
Save 100% on your flight
Price was $1,341, price is now $682 per person
$682
per person
Mar 8 - Mar 15
found 16 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Was crowded due to the holiday season. Expected better prepardeness from a name brand chain like Sheraton for the holiday rush. The staff was overwhelmed all the time and evidently ‘doing their job’. Guests were there on vacation. There should have been some empathy from the staff in their interactions. Supremely disappointing
Reviewed on Jan 5, 2026
NobleDEN Hotel
Manhattan
Price was $1,638, price is now $862 per person
$862
per person
Mar 8 - Mar 15
found 16 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
This was our first time in NYC and we loved it from the moment we arrived in Little Italy and our hotel. We loved the view, and with the holiday lights still up it was very festive. The room was modern, attractive, and very comfortable. We plan to return!
Reviewed on Jan 4, 2026
Hotel St. James
Manhattan
Price was $1,423, price is now $755 per person
$755
per person
Mar 8 - Mar 15
found 16 hours ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
Not the greatest rooms and had to be asked to move. New room was okay but bathroom was extremely tiny and no fridge and new room bathtub didn’t work with drain. Not the best
Reviewed on Jan 4, 2026
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
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Jan 20 to Jan 21
$107 total
Jan 20 - Jan 21
Total with taxes and fees
8.8/10 Excellent! (1,024 reviews)
Room was great, and it’s nice to still rent a hotel room that has carpet in it. The staff was fantastic, I couldn’t say more positive things about this hotel.
Reviewed on Jan 4, 2026
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Jan 23 to Jan 24
$118 total
Jan 23 - Jan 24
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
All good. Thanks.
Reviewed on Dec 29, 2025
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $114 total per night from Jan 8 to Jan 9
$114 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
I was unable to attend breakfast this time as I had to run off in the morning but I enjoyed a nice hot shower.
Reviewed on Dec 28, 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.
