Dutchess County Holidays

Photo by J&M Explorations

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

FlightsFlightsHotelsHotels

Beacon

Beacon

Dutchess County Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was S$2,537, price is now S$1,902 per person
S$1,902
per person
22 Mar - 28 Mar
found 9 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Amazing staff!! Room was chilly despite the heat being on and high, better windows definitely needed, other than this, no complaints!

Reviewed on 30 Dec, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was S$3,306, price is now S$2,246 per person
S$2,246
per person
22 Mar - 28 Mar
found 9 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Highly recommend. Staff went above and beyond to assist us with WiFi troubles, sending an engineer to our room (arriving within 5min) and resetting the router which was located in our ceiling. The breakfast buffet was also fantastic and well organized.

Reviewed on 5 Jan, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was S$3,042, price is now S$2,131 per person
S$2,131
per person
22 Mar - 28 Mar
found 9 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The staff was the best! Super friendly and helpful!

Reviewed on 6 Jan, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was S$2,743, price is now S$2,016 per person
S$2,016
per person
22 Mar - 28 Mar
found 9 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.8/10 Excellent! (6,546 reviews)
This hotel was clean and friendly and close to time square. Everything was within walking distance and my second time stay here.

Reviewed on 6 Jan, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was S$3,525, price is now S$2,737 per person
S$2,737
per person
22 Mar - 28 Mar
found 9 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.4/10 Very Good! (1,000 reviews)
Room was clean but had marks on the wall. Tiny bathroom. Staff was friendly. Good breakfast.

Reviewed on 4 Jan, 2026

Top hotels in Dutchess County

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 S$130 per night from 22 Jan to 23 Jan
S$130
22 Jan - 23 Jan
includes taxes & fees
8.8/10 Excellent! (1,023 reviews)
Yes

Reviewed on 2 Jan, 2026

Courtyard by Marriott 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 S$151 per night from 16 Jan to 17 Jan
S$151
16 Jan - 17 Jan
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
All good. Thanks.

Reviewed on 29 Dec, 2025

Hampton Inn & Suites Poughkeepsie
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 S$147 per night from 19 Jan to 20 Jan
S$147
19 Jan - 20 Jan
includes taxes & fees
8.8/10 Excellent! (1,023 reviews)
Quick and easy! Friendly greeting and thorough.

Reviewed on 4 Jan, 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 401 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 S$1,902, 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.