Dutchess County Vacations & Trips from ￥267,538

Book a Hotel + Flight or Car together to unlock savings

Photo by Geo M

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Dutchess County

Rhinebeck showing a city
FlightsFlightsHotelsHotels

Rhinebeck

Rhinebeck

The Latest Dutchess County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was ￥399,736, price is now ￥267,538 per person
￥267,538
per person
May 2 - May 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Rooms Property were Fantastic !

Reviewed on Feb 6, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥640,992, price is now ￥422,746 per person
￥422,746
per person
May 2 - May 8
found 4 hours ago
Roundtrip flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,790 reviews)
Great hotel, our room was warm and clean. The staff were very helpful and friendly. It was quite busy considering it was January but they were very organised. The breakfast selection was wonderful. Would recommend this hotel.

Reviewed on Feb 8, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥664,242, price is now ￥454,600 per person
￥454,600
per person
Apr 26 - Apr 30
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (638 reviews)
Close to major shopping and multiple dining options

Reviewed on Jan 21, 2026

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was ￥623,091, price is now ￥427,286 per person
￥427,286
per person
May 2 - May 8
found 4 hours ago
Roundtrip flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,723 reviews)
Very pleased. Excellent service. Thank you

Reviewed on Feb 7, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was ￥560,032, price is now ￥384,658 per person
￥384,658
per person
May 2 - May 8
found 4 hours ago
Roundtrip flight included
Tokyo (HND) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Everything was excelent! Clean, everybody was very nice

Reviewed on Feb 8, 2026

Dutchess County Hotel Deals

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is ￥16,508 per night from Feb 16 to Feb 17
￥16,508
￥18,674 total
Feb 16 - Feb 17
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Room was nice. Staff was friendly

Reviewed on Feb 7, 2026

Courtyard by Marriott Poughkeepsie
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 ￥15,986 per night from Feb 21 to Feb 22
￥15,986
￥18,725 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Room was clean and comfortable. Staff was so friendly. Would definitely stay here again

Reviewed on Jan 29, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
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 ￥14,052 per night from Feb 20 to Feb 21
￥14,052
￥16,317 total
Feb 20 - Feb 21
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Best staff ever great location.

Reviewed on Feb 1, 2026

Hampton Inn & Suites Poughkeepsie
See all 3,864 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 ￥267,538, 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.