Dutchess County Vacations & Trips from $423
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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.
Delta Hotels by Marriott Woodbridge
Save 100% on your flight
Price was $682, price is now $423 per person
$423
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,004 reviews)
Location and good that they have a indoor pool.
Reviewed on Feb 9, 2026
Topping Rose House
Save 100% on your flight
Price was $3,047, price is now $1,800 per person
$1,800
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (143 reviews)
Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower.
But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker.
Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very inconvenient to check the outfit before heading out the door.
It’s little odd things that just made it not feel like a luxury stay.
And no one mentioned to us beforehand that the sauna, gym, pool area (even though in off season) was under renovation and not available to use.
The restaurant was amazing though, room service was wonderful. And staff were adorable. But I don’t know if we would book again tbh.
Reviewed on Mar 24, 2026
INNSiDE by Meliá New York Nomad
Manhattan
Save 100% on your flight
Price was $1,807, price is now $1,076 per person
$1,076
per person
Jun 6 - Jun 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,221 reviews)
I do not take my dog with me on trips but it did look pet friendly.
A/c was great
Reviewed on Mar 25, 2026
1 Hotel Brooklyn Bridge
Save 100% on your flight
Price was $2,224, price is now $1,339 per person
$1,339
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,000 reviews)
Excellent staff, clean room, fantastic onsite restaurants.
Reviewed on Mar 10, 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
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $134 total per night from Apr 3 to Apr 4
$134 total
Apr 3 - Apr 4
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
The breakfast menu was fresh and the coffee at all times was a nice perk. The staff at checkout was rude and even though we had asked for adjoining rooms, we were not provided that at check in. We were instead given rooms on opposite floors. There was something spilled on the side table and something ...
Reviewed on Mar 27, 2026
Courtyard by Marriott Fishkill
17 Westage Drive Fishkill NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Mar 30 to Mar 31
$114 total
Mar 30 - Mar 31
Total with taxes and fees
8.8/10 Excellent! (760 reviews)
Staff was very nice . Gave us water bottles , and i loved that they didn’t come knocking on the door as soon as it was checkout time
Reviewed on Mar 18, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
OK
Reviewed on Mar 24, 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.
