Dutchess County Vacations & Trips from ￥297,763

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    Save up to ￥45,448 when you book a flight and hotel together*

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Top destinations in Dutchess County

Rhinebeck showing a city
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Rhinebeck

Rhinebeck
Exploring an old abandoned brick factory!!!
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Beacon

Beacon

The Latest Dutchess County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥473,537, price is now ￥297,763 per person
￥297,763
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (NYC)
9.8/10 Exceptional! (1,377 reviews)
Staff were wonderful as always.

Reviewed on Nov 8, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was ￥771,294, price is now ￥541,968 per person
￥541,968
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.6/10 Exceptional! (151 reviews)
A perfect place to stay!!

Reviewed on Sep 20, 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Price was ￥447,671, price is now ￥314,872 per person
￥314,872
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.4/10 Very Good! (24 reviews)
We wanted a clean room to sleep. It was quite clean. Out expectations were met. Staff was very nice and helpful. Shared bathroom was not a problem.

Reviewed on Oct 12, 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was ￥612,020, price is now ￥432,453 per person
￥432,453
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (1,646 reviews)
Loved everything about this hotel and will stay again for sure

Reviewed on Nov 5, 2025

Dutchess County Hotel Deals

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is ￥15,219 per night from Dec 5 to Dec 6
￥15,219
￥17,674 total
Dec 5 - Dec 6
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
This hotel excelled in every area! Great service, comfy beds, clean, the free breakfast was really good! Recommend 100%

Reviewed on Nov 7, 2025

Hampton Inn & Suites Poughkeepsie
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 out of 5
849 Route 52, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is ￥16,510 per night from Dec 7 to Dec 8
￥16,510
￥18,677 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Clean room, staff very helpful and friendly

Reviewed on Nov 8, 2025

Quality Inn & Suites Fishkill South near I-84
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is ￥15,993 per night from Nov 26 to Nov 27
￥15,993
￥18,733 total
Nov 26 - Nov 27
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Spotless room, friendly staff, convenient parking and great location for events at Bardavon, Hudson pedestrian bridge in walking distance. We'd stay here again!

Reviewed on Oct 31, 2025

DoubleTree by Hilton Poughkeepsie Convention Center
See all 418 properties in Dutchess County
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 ￥297,763, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.