Dutchess County Vacation Packages
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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 vacation destinations in Dutchess County
Poughkeepsie
Rhinebeck
Top Dutchess County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Dutchess County Hotel Deals
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $146
CA $170 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,031 reviews)
"Rude staff"
Reviewed on Aug 9, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
CA $171
CA $193 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very good! (961 reviews)
"The staff showed us a map to find the Delacanter however it was challenging. Also our room had insufficient air. It was clean but security was questionable as all exterior doors were open all the time but no building attendant on premises but you had a number to call. Rooms had a lock. Breakfast ..."
Reviewed on Aug 8, 2026
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $108
CA $125 total
Sep 9 - Sep 10
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"We have stayed at this hotel before and once again, I was pleased with the location, the friendly staff, and the ample breakfast."
Reviewed on Aug 9, 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.
Frequently asked questions
How much does a Dutchess County vacation package cost?
Our Dutchess County packages, which start from as low as CA $1,066, 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)
Enjoy the collegiate vibe when you visit Culinary Institute of America, during your travels in Hyde Park. Wander the area's riverfront or simply enjoy one of its top-notch restaurants.
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.
Franklin D. Roosevelt Presidential Library and Museum
9.6/10 (249 reviews)
The country’s first presidential library documents the life and works of the revered leader who served as the 32nd U.S. president.
Photo by (yu+ma)
Dia Beacon
8.6/10 (261 reviews)
You can spend an afternoon studying the exhibits at Dia Beacon during your trip to Beacon. While you're in the area, stroll along the riverfront.
Vanderbilt Mansion National Historic Site
9.6/10 (108 reviews)
Explore the garden and mansion of this country house that is among the oldest from the Gilded Age along the Hudson River.
SplashDown Beach
8.0/10 (97 reviews)
Bring the kiddos to SplashDown Beach and enjoy some excitement at this theme park in Fishkill. Stroll along the riverfront or attend a sporting event in the area.
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)
Enjoy a stop at Dutchess County Fairgrounds, an entertaining place to visit in Rhinebeck. Stroll along the marina or experience the area's festivals.
What to do in Dutchess County
Discover New York City: 6+ Must-See Self-Guided Walking Audio Tours
CA $70
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
