Dutchess County Holidays
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Your Dutchess County Holiday
Choose a holiday 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 holiday is only clicks away with Expedia.
Top destinations in Dutchess County
Poughkeepsie
Beacon
Rhinebeck
Hyde Park
Wappingers Falls
Amenia
Top Dutchess County Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
£1,959
per person
8 Dec - 13 Dec
found 24 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,026 reviews)
The hotel was a perfect location. It was beautiful and our room was very nice!
Reviewed on 6 Oct 2026
Hotel Riu Plaza New York Times Square
Manhattan
£1,870
per person
8 Dec - 13 Dec
found 24 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,389 reviews)
Room was clean and front desk staff were awesome! Breakfast was delicious and well organized with a lot of food choices
Reviewed on 5 Oct 2026
Dutchess County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Top Sights | Innisfree Garden, Bowdoin Park and Harlem Valley Rail Trail |
Top hotels in Dutchess County
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
£92
26 Oct - 27 Oct
includes taxes & fees
9/10 Wonderful! (1,102 reviews)
"Nice, clean comfortable place to stay. Staff was super friendly. Shout out to Grace at the front desk for being very helpful. Only thing room lacked was a microwave."
Reviewed on 5 Oct 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
£115
27 Oct - 28 Oct
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"I was up early during my stay but around 7:15 am leaf blowers were being used across the street. It probably woke up everyone in the building where I was staying."
Reviewed on 5 Oct 2026
Comfort Suites Fishkill near Interstate 84
835 Route 52 Fishkill NY
Fully refundableReserve now, pay when you stay
£85
2 Nov - 3 Nov
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 travel package cost?
Our Dutchess County travel packages, which start from as low as £1,312, are an awesome way to save big. Handpick your favourite hotels, flights and rental car to create your perfect itinerary.
If I'm not able to travel, can I cancel my Dutchess County travel package?
If your travel plans in Dutchess County have been upended, it's comforting to know that you can cancel your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking is older than that, your hotel, airline or car rental company may charge a cancellation fee. To learn more, visit our Customer Service Portal.
How do I get a cheap travel package to Dutchess County?
Combine your bookings with Expedia to save on your next getaway. With over 550 partner airlines and 1,000,000 properties throughout the world, your Dutchess County holiday package can be tailored exactly to suit your travel style. With all that extra cash, why not include one or more awesome tours and experiences? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Dutchess County is closer than you thought!
Does Expedia offer Book Now, Pay Later Dutchess County holidays?
Expedia has joined forces with online lender Klarna to make your next getaway easier on your bank balance. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Consider these flexible payment options:
- Pay monthly holidays: Klarna has convenient monthly payment plans that work for all types of budgets, so you can book that well-earned holiday sooner.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday over multiple transactions.
- Low deposit holidays: Clicking the "book now" button is much easier with this option. Just put down a small deposit on your holiday and then start working on your travel plans.
What are the top hotels in Dutchess County?
When it comes to properties in Rhinebeck, HYATT house Fishkill/Poughkeepsie and Hyatt Place Poughkeepsie are among the favourites. If you're also visiting Red Hook, HYATT house Fishkill/Poughkeepsie and Hyatt Place Poughkeepsie look forward to welcoming you.
How far in advance should I book my Dutchess County holiday?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you can't book ahead, don't stress. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Dutchess County travel package include?
Hotels, flights and a shiny set of wheels for your road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to organising your Dutchess County break, you're the boss!
What should I know before booking a Dutchess County travel package?
Bundling your bookings into a Dutchess County travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Dutchess County Expedia travel package?
Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Dutchess County escape.
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)
Explore the campus of Bard College during your stay in 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, savour 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 railway museum. Explore original features and model trains while enthusiasts share stories.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
