Dutchess County Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top destinations in Dutchess County
Poughkeepsie
Beacon
Rhinebeck
Fishkill
Hyde Park
Wappingers Falls
Red Hook
Amenia
Millbrook
The Latest Dutchess County Holiday Packages
- JW Marriott Essex House New York
1 Feb - 4 FebJW Marriott Essex House New York + Flight
Manhattan3 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€1,679€1,260found 17 hours agoper traveller - The St. Regis New York
2 Jan - 5 JanThe St. Regis New York + Flight
Manhattan3 nights5.0 star property9.2/10 - Wonderful (295 reviews)"The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"Reviewed November 6, 2026Return • Dublin (DUB) - New York (JFK)DUB - EWR • Direct LGA - DUB • 1 stop€3,571€2,514found 10 hours agoper traveller - Hotel Beacon
28 Dec - 1 JanHotel Beacon + Flight
Manhattan4 nights4.0 star property9.4/10 - Exceptional (1,558 reviews)Return • Lisbon (LIS) - New York (JFK)LIS - EWR • Direct EWR - LIS • Direct€2,414€1,848found 1 day agoper traveller - PUBLIC, an Ian Schrager hotel
9 Dec - 12 DecPUBLIC, an Ian Schrager hotel + Flight
Manhattan3 nights4.0 star property8.8/10 - Excellent (4,095 reviews)Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct€2,121€1,672found 1 day agoper traveller - Ink 48 Hotel
19 Dec - 23 DecInk 48 Hotel + Flight
Manhattan4 nights4.5 star property8.4/10 - Very good (1,830 reviews)"Beautiful bathroom, room was largest I’ve experienced in NYC, staff were very helpful but our room was located right across from a very noisy bar."Reviewed November 7, 2026Return • Lisbon (LIS) - New York (JFK)LIS - EWR • Direct EWR - LIS • 1 stop€1,830€1,464found 1 day agoper traveller
Discover the most popular places to visit in Dutchess County
Culinary Institute of America
Vanderbilt Mansion National Historic Site
What to do in Dutchess County
Self-Guided Audio Driving Tour in Catskills Scenic Byway
Dutchess County Hotel Deals
Homewood Suites by Hilton Poughkeepsie
Homewood Suites by Hilton Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley
Hyatt Place Poughkeepsie / Hudson Valley
Holiday Inn Express Poughkeepsie by IHG
Holiday Inn Express Poughkeepsie by IHG
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
DoubleTree by Hilton Poughkeepsie Convention Center
DoubleTree by Hilton Poughkeepsie Convention Center
Hampton Inn & Suites Poughkeepsie
Hampton Inn & Suites Poughkeepsie"Everything was clean. Breakfast was good. Only problem was that the pool was closed during our stay and we were looking forward to it. But otherwise, everything else was great."
Beekman Arms and Delamater Inn
Beekman Arms and Delamater InnFrequently Asked Questions
How much does a Dutchess County holiday package cost?
Our Dutchess County packages, which start from as low as €1,260, are the perfect way to save. Handpick your favourite 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 holiday 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 holiday 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 travellers.
How far in advance should I book my Dutchess County holiday?
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 holiday. 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 holiday 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 holiday rentals like beach villas and spacious residences. The list goes on!
Can I choose my airline with a Dutchess County Expedia holiday 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 holiday package?
If your holiday 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.