Dutchess County Holidays from AU$2,326

Book a Hotel + Flight or Car together to unlock savings

Photo by J&M Explorations

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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

Your Dutchess County Holiday

Choose a holiday package to Dutchess County and make planning your adventure easy. With the logistics arranged before you leave, you can focus on enjoying every minute in this exciting destination. With so much to see on a trip to Dutchess County, it can be hard to know where to begin. Kick off your journey in Poughkeepsie at Vanderbilt Mansion National Historic Site and Hyde Park Station — two much-loved attractions here. Another great city worthy of a spot on your itinerary is Pawling. Be sure not to miss Candlewood Lake and Stormville Airport Antique Show & Flea Market. Find some travel buddies and start packing, because your Dutchess County holiday is only clicks away with Expedia.

Top destinations in Dutchess County

Poughkeepsie showing autumn colours and a river or creek
FlightsFlightsHotelsHotels

Poughkeepsie

Poughkeepsie

The Latest Dutchess County Holiday Deals

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

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was AU$3,329, price is now AU$2,326 per person
AU$2,326
per person
24 Jan - 31 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9.2/10 Wonderful! (3,941 reviews)
Amazing room and view

Reviewed on 17 Dec 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was AU$4,511, price is now AU$3,077 per person
AU$3,077
per person
10 Mar - 17 Mar
found 2 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Staff was great, room was great, hotel was clean.

Reviewed on 17 Dec 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was AU$3,752, price is now AU$2,660 per person
AU$2,660
per person
24 Jan - 31 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
Nice enjoyable stay!

Reviewed on 16 Dec 2025

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was AU$7,160, price is now AU$5,127 per person
AU$5,127
per person
10 Mar - 17 Mar
found 2 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (591 reviews)
This is a wonder hidden gem of a hotel

Reviewed on 1 Dec 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was AU$3,512, price is now AU$2,539 per person
AU$2,539
per person
24 Jan - 31 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
Very cute and well appointed room! Lovely staff. Free coffee and tea.

Reviewed on 15 Dec 2025

Dutchess County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Top Sights
Bowdoin Park, Fishkill Ridge and Innisfree Garden

Our pick of the best Dutchess County Hotel Deals

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 AU$164 per night from 27 Dec to 28 Dec
AU$164
27 Dec - 28 Dec
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back.

Reviewed on 16 Dec 2025

Hampton Inn & Suites Poughkeepsie
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 AU$162 per night from 4 Jan to 5 Jan
AU$162
4 Jan - 5 Jan 2026
includes taxes & fees
7.6/10 Good! (498 reviews)
Room was clean. Staff was kind. Good complimentary breakfast

Reviewed on 23 Nov 2025

Quality Inn 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 AU$177 per night from 28 Dec to 29 Dec
AU$177
28 Dec - 29 Dec
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Clean, modern, plenty amenities, attentive service. Will come back again- thank you!

Reviewed on 14 Dec 2025

Hyatt Place Poughkeepsie / Hudson Valley
See all 403 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Dutchess County holiday package cost?
Our Dutchess County packages, which start from as low as AU$2,326, 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 homes 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.