Dutchess County Vacations & Trips from $892
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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
Poughkeepsie
Rhinebeck
Fishkill
Hyde Park
Wappingers Falls
Millbrook
Amenia
The Latest Dutchess County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace
Manhattan
$892
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,282 reviews)
Beautiful property and location with views of St. Patrick’s and Radio City. A gorgeous hotel and professional staff. We stay here often!
Reviewed on Oct 6, 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
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
$101 nightly
$117 total
Nov 5 - Nov 6
Total with taxes and fees
9/10 Wonderful! (1,103 reviews)
"Clean and comfortable Large room needs better lighting No room service just a nook/bar downstairs where they make drinks and some offerings of food. Breakfast included but I did not have any- set up looked ok. Entrance is to Storage place so I Missed it the first time around. I would stay again."
Reviewed on Oct 6, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
$152 nightly
$172 total
Oct 8 - Oct 9
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"The Inn was very quaint. The staff was nice and the rooms were appointed well. The town is delightful!"
Reviewed on Oct 6, 2026
Comfort Suites Fishkill near Interstate 84
835 Route 52 Fishkill NY
$98 nightly
$113 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,013 reviews)
"Pretty good in general"
Reviewed on Oct 6, 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.
Photo by Irishbelle30
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.
Hyde Park Station
8.2/10 (282 reviews)
This 1914 Mission-style station, designed by Grand Central Terminal's architects, houses a captivating railroad museum. Explore original features and model trains while enthusiasts share stories.
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