Dutchess County Holidays

Photo by Geo M

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Top destinations in Dutchess County

FlightsFlightsHotelsHotels

Poughkeepsie

Poughkeepsie
Hazy sunset over country road in the mountains upstate NY
FlightsFlightsHotelsHotels

Amenia

Amenia

Top Flight + Hotel Deals in Dutchess County

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Price was €1,480, price is now €1,081 per person
€1,081
per person
4 Aug - 8 Aug
just found
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
Elevators could use some work.

Reviewed on 23 Jun 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was €2,372, price is now €1,611 per person
€1,611
per person
24 Aug - 30 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,014 reviews)
The bartender Sunny in the bar. Can't keep up with the crowd and forgets a lot.

Reviewed on 23 Jun 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was €1,794, price is now €1,325 per person
€1,325
per person
4 Aug - 8 Aug
just found
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,080 reviews)
Perfect location, clean breakfast was just super hard to get to was very busy but overall would stay again Forsure

Reviewed on 24 Jun 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €1,739, price is now €1,297 per person
€1,297
per person
4 Aug - 8 Aug
just found
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,636 reviews)
Easy check in, clean, and professional

Reviewed on 24 Jun 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was €1,448, price is now €1,108 per person
€1,108
per person
4 Aug - 8 Aug
just found
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Location is great but No water or coffee available at the hotel . Room has window AC unit that was very loud. The room was very small

Reviewed on 24 Jun 2026

Top hotels in Dutchess County

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is €125 per night from 28 Jun to 29 Jun
€125
28 Jun - 29 Jun
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Nice, spacious room. Comfy bed, fluffy towels. Good breakfast!"

Reviewed on 24 Jun 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is €94 per night from 8 Jul to 9 Jul
€94
8 Jul - 9 Jul
includes taxes & fees
8.2/10 Very good! (141 reviews)
"Neat, nice stay, good location."

Reviewed on 24 Jun 2026

Spark by Hilton Fishkill
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 €112 per night from 28 Jun to 29 Jun
€112
28 Jun - 29 Jun
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"I arrived and was informed that there was no air conditioning or hot water at the hotel. They said they had reached out to other hotels to accommodate their guests. They moved me to a new hotel where I had to book a new room and pay for it out of pocket. They said I would be refunded but then refused ..."

Reviewed on 22 Jun 2026

DoubleTree by Hilton Poughkeepsie Convention Center
See all 402 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 holiday package cost?
Our Dutchess County packages, which start from as low as €1,081, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.