Dutchess County Vacations & Trips from ￥271,967

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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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 4 - Sep 9
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,729 reviews)
Great clean neat facility!!!!

Reviewed on Jun 16, 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,511 reviews)
If you want to be in Times Square this is the perfect location, has great restaurants and an amazing rooftop bar. As for the rooms, this hotel is not 5 * more like 4 at best. The rooms are not as shown on marketing materials but much smaller and barely a window. I felt very confined in the room and had to get a different room with more windows so I didn't feel trapped.

Reviewed on Jun 12, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,408 reviews)
This hotel was right in Times Square. The subway stops are very close as well. It was clean and I had no issues. A great location!

Reviewed on Jun 17, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,108 reviews)
The rooms were large (for Manhattan) and the location was great for subways and trains out of Penn Station. Would definitely stay here again.

Reviewed on Jun 17, 2025

Park Central Hotel New York

Park Central Hotel New York

4 out of 5
Manhattan
per person
Sep 11 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to New York (JFK)
7.8/10 Good! (3,441 reviews)
Excellent Hotel Ana at the front desk is a treasure

Reviewed on Jun 19, 2025

Dutchess County Hotel Deals

HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is ￥16,149 per night from Jul 6 to Jul 7
￥16,149
￥18,268 total
Jul 6 - Jul 7
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Very nice, updated, clean and price was great. Pool and hot tub were also great."

Reviewed on Jun 18, 2025

HYATT house Fishkill/Poughkeepsie
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 ￥16,859 per night from Jul 1 to Jul 2
￥16,859
￥19,577 total
Jul 1 - Jul 2
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Thank you for all the wonderful service and beautiful hotel. It was the perfect spot for our family to gather for my grandmas funeral."

Reviewed on Jun 18, 2025

Hampton Inn & Suites Poughkeepsie
Beekman Arms Hotel
Beekman Arms Hotel
3.5 out of 5
6387 MILL ST, Rhinebeck, NY
8.2/10 Very Good! (716 reviews)
"This is the oldest continuously operating inn in the U.S. The floors are somewhat slanted and have beautiful boards, often original. The Arms is in the middle of the village."

Reviewed on Jun 17, 2025

Get rates
Beekman Arms Hotel
See all 424 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 ￥271,967, 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.