Dutchess County Vacations & Trips from ₩664,173
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Top destinations in Dutchess County
Poughkeepsie
Beacon
The Latest Dutchess County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
₩696,125
per person
Oct 18 - Oct 20
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
6.8/10 (2,082 reviews)
The check in was quick and easy. The hotel was in a prime location in Times Square. The AC in the room was not working and front desk sent up a fan. We were only there to 2 nights so we made it.
Reviewed on Sep 8, 2026
PUBLIC, an Ian Schrager hotel
Manhattan
₩1,610,493
per person
Nov 23 - Nov 28
found 14 hours ago
Roundtrip flight included
Omaha (OMA) to New York (JFK)
8.8/10 Excellent! (3,947 reviews)
I love the ambiance of the place. I stayed in a queen bed room which was a little smaller than the king we stayed in the last time we were here. Overall I love it here. The room, the rooftop, the lounge, Everything!!
Reviewed on Sep 8, 2026
Dutchess County Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
₩180,634
₩204,343 total
Sep 9 - Sep 10
includes taxes & fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
₩110,990
₩128,888 total
Sep 13 - Sep 14
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
₩135,896
₩157,810 total
Sep 22 - Sep 23
includes taxes & fees
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.
Frequently asked questions
How much does a Dutchess County vacation package cost?
Our Dutchess County packages, which start from as low as ₩664,173, are the perfect way to save. Handpick your favorite flights, hotels and rental cars to create your dream escape.
How do I get a cheap travel package to Dutchess County?
Bundle your hotels and flights with Expedia to save big bucks on your next exciting adventure. With more than 550 airlines and 1,000,000 hotel options worldwide, your Dutchess County vacation package can be tailored exactly to suit your budget. With all that extra cash, why not include a few fun activities and tours? It's an easy way to unlock even more savings. That vacation you've always dreamed of in Dutchess County is closer than you thought!
What are the top hotels in Dutchess County?
Royal Regency Hotel and Tru By Hilton Albany Airport, NY know how to make their guests feel welcome in Rhinebeck. If you also plan to get to Poughkeepsie, take a look at Courtyard by Marriott Yonkers Westchester County and Hampton Inn & Suites Albany Airport. Both are very popular with travelers.
How far in advance should I book my Dutchess County vacation?
While prices fluctuate, we generally recommend booking your spot as early as possible. Most international airfares are available on Expedia up to 12 months in advance. If you're booking late, you might still be in luck. Cheaper tickets to Dutchess County sometimes appear in the weeks prior to departure.
What does an Expedia Dutchess County travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your dream Dutchess County vacation. You can also add on activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Dutchess County travel package?
Locking in all the parts of your vacation together is one of the best ways to save. Combine your flights, car rentals and hotels into a tidy package. But hotels aren't your only option. Expedia offers all kinds of properties, including vacation rentals like beach villas and spacious residences. The list goes on!
Can I choose my airline with a Dutchess County Expedia vacation package?
Yes, so take your pick! We have access to over 550 partner airlines around the world, so you can design your Dutchess County adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Dutchess County vacation package?
If your vacation plans in Dutchess County have been upended, it's good to know that you can amend or cancel your booking. If your booking was made less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a fee. To find out more, check our Customer Service Portal.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
