Dutchess County Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
EVEN Hotel New York - Midtown East by IHG

EVEN Hotel New York - Midtown East by IHG

4 out of 5
Manhattan
Price was S$7,239, price is now S$6,102 per person
S$6,102
per person
29 Oct - 5 Nov
found 19 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.8/10 Excellent! (1,473 reviews)
Great location, super clean and friendly staff.

Reviewed on 19 Aug, 2025

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was S$12,285, price is now S$10,320 per person
S$10,320
per person
29 Oct - 5 Nov
found 19 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (235 reviews)
Beautiful hotel from the gilded age. Outstanding service. Beautiful and delicious breakfast.

Reviewed on 4 Jul, 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Price was S$8,095, price is now S$6,964 per person
S$6,964
per person
29 Oct - 5 Nov
found 19 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.4/10 Very Good! (2,958 reviews)
Loved everything about this place!

Reviewed on 23 Aug, 2025

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was S$7,423, price is now S$6,402 per person
S$6,402
per person
29 Oct - 5 Nov
found 19 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (3,976 reviews)
Kalsang was super helpful! He was so kind. Property has a gorgeous view, pool was nice. All the staff was friendly.

Reviewed on 26 Aug, 2025

Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Manhattan
Price was S$7,787, price is now S$6,724 per person
S$6,724
per person
29 Oct - 5 Nov
found 19 hours ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.2/10 Very Good! (1,327 reviews)
The air conditioner in the room was really loud lol. That's about it.

Reviewed on 23 Aug, 2025

Top hotels in Dutchess County

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 21 Sept to 22 Sept
S$152
21 Sept - 22 Sept
includes taxes & fees
7.6/10 Good! (403 reviews)
"Overall good stay"

Reviewed on 24 Aug, 2025

Quality Inn 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 S$142 per night from 7 Sept to 8 Sept
S$142
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
Nice place to stop off I84
"Check in woman was super friendly. Room was spacious, clean and comfortable. Traveling with my daughter and this was about our halfway point. Its right off of I84, next to a diner that appeared to be well known due to how busy it looked, and a gas station down the street. Hotel was quiet and couldnt ..."

Reviewed on 25 Aug, 2025

Quality Inn & Suites Fishkill South near I-84
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is S$116 per night from 7 Sept to 8 Sept
S$116
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"We were only there for one night but staff was really nice and rooms were clean. Breakfast was good also."

Reviewed on 24 Aug, 2025

Quality Inn Hyde Park Poughkeepsie North
See all 421 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$6,102, 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.