Dutchess County Vacations & Trips from $924
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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
Fishkill
Wappingers Falls
Poughkeepsie
Rhinebeck
Hyde Park
Millbrook
Amenia
The Latest Dutchess County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Gotham Hotel
Manhattan
$997
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,051 reviews)
The hotel felt modern, clean and spacious. Slightly noisy at night but that's Midtown. Couldn't access the hotel bar either night because of private events. Staff were polite and helpful. Would definitely recommend.
Reviewed on Sep 25, 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
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
$97 nightly
$113 total
Oct 21 - Oct 22
Total with taxes and fees
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$152 nightly
$172 total
Sep 27 - Sep 28
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"I was extremely disappointed to have made a reservation with the Beekman Inn, only to be redirected to a generic room by the conference center. I specifically wanted an OLD INN; I was not there for a conference! The room was fine and the breakfasts adequate. I was a single traveler charged as a couple. ..."
Reviewed on Sep 25, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
$109 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,083 reviews)
"Very clean property! Nice room and staff were all very helpful!"
Reviewed on Sep 25, 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.
Stay near popular Dutchess County attractions
Photo by Gregg Tobias
Culinary Institute of America
9.2/10 (275 reviews)
This prestigious culinary college offers a rare chance to dine at student-run restaurants showcasing future chefs. Reserve a table at The Bocuse Restaurant for modern French cuisine with Hudson River views.
Bard College
8.6/10 (100 reviews)
Enjoy the collegiate vibe at Bard College during your visit to Annandale-on-Hudson. Stroll along the marina or experience the area's festivals.
Photo by (yu+ma)
Dia Beacon
8.6/10 (261 reviews)
Housed in a former Nabisco factory, Dia:Beacon showcases monumental contemporary art bathed in natural light. Explore spacious galleries featuring works by Richard Serra and Dan Flavin in this riverside museum.
Franklin D. Roosevelt Presidential Library and Museum
9.6/10 (249 reviews)
America's first presidential library, designed by FDR himself, offers an intimate look at the Roosevelt era through original documents, exhibits, and personal collections in this Hudson Valley treasure.
Vanderbilt Mansion National Historic Site
9.6/10 (108 reviews)
Step into America's Gilded Age at this Beaux-Arts masterpiece, once home to the Vanderbilt fortune. The mansion's 54 opulent rooms and Hudson River views offer a glimpse into elite 19th-century living.
Omega Institute
9.2/10 (31 reviews)
Take a campus tour or just explore the area of Omega Institute, during your travels in Rhinebeck. Stroll along the riverfront or experience the area's festivals.
Dutchess County Fairgrounds
8.8/10 (66 reviews)
The Dutchess County Fairgrounds hosts NY's premier six-day county fair and year-round special events. Explore agricultural exhibits, savor gourmet fair treats, and experience the Hudson Valley Wine & Food Fest.
SplashDown Beach
8.0/10 (97 reviews)
SplashDown Beach offers 25 water attractions, including the towering Arctic Mammoth raft ride. Families can enjoy thrilling slides, relaxing pools, and shaded seating areas during the summer season.
What to do in Dutchess County
Hallows and Hauntings of Hyde Park Ghost Tour
$32
per adult
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