Dutchess County Holiday Packages

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A river with boats docked on the shore, surrounded by autumn-colored trees.
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Poughkeepsie

Poughkeepsie
A rural road flanked by dense greenery and power lines under a cloudy sky.
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Amenia

Amenia

Top Dutchess County holiday packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was AU$7,284, price is now AU$4,314 per person
AU$4,314
per person
16 Nov - 23 Nov
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Save 100% on your flight
Price was AU$18,798, price is now AU$10,774 per person
AU$10,774
per person
16 Nov - 23 Nov
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.4/10 Very good! (5 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was AU$9,651, price is now AU$5,811 per person
AU$5,811
per person
16 Nov - 23 Nov
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,010 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was AU$9,818, price is now AU$6,229 per person
AU$6,229
per person
16 Nov - 23 Nov
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (706 reviews)

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was AU$7,150, price is now AU$4,575 per person
AU$4,575
per person
16 Nov - 23 Nov
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)

Top Dutchess County hotels

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
The price is AU$163 per night from 2 Nov to 3 Nov
AU$163
2 Nov - 3 Nov
includes taxes & fees
Comfort Suites Fishkill near Interstate 84: Business-friendly hotel with free breakfast and free WiFi. Located near a metro station.
"The room was spacious, clean and comfortable. There was a large television, which I enjoyed. Unfortunately, the cable service was spotty."

Reviewed on 4 Oct 2026

Opens in a new windowComfort Suites Fishkill near Interstate 84
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
The price is AU$175 per night from 26 Oct to 27 Oct
AU$175
26 Oct - 27 Oct
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley: Pet-friendly hotel with free breakfast and free WiFi. Located in the historical district.
Opens in a new windowHyatt Place Poughkeepsie / Hudson Valley
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
The price is AU$218 per night from 25 Oct to 26 Oct
AU$218
25 Oct - 26 Oct
includes taxes & fees
Beekman Arms and Delamater Inn: Pet-friendly inn with free breakfast and free WiFi. Located near a train station.
Opens in a new windowBeekman Arms and Delamater Inn
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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.

Your guide to epic deals and sweet holiday packages to Dutchess County

How much are holiday packages to Dutchess County?

You can book an awesome holiday in Dutchess County from just AU$4,314 on Wotif. Check our deal cards for details.

What’s included in Wotif’s Dutchess County holiday package deals?

Dutchess County packages can bundle everything: flight + hotel + car hire. But you can go for hotel + car hire without the flight. Or flight + hotel. You do you.

Can I cancel my Dutchess County holiday plans on Wotif?

Yes. Within 24 hours of booking, you can cancel and get your money back on many of our packages. After 24 hours, your airline or hotel may charge a fee. Check your itinerary or our Customer Service Portal to know more.

How do I find the best holiday package to Dutchess County?

Just take a look through all our terrific offers or select your dream spot in Dutchess County, and we’ll serve up some delicious Dutchess County holiday deals that’ll make you swoon and save you cash.

How do I get the best holiday deals to Dutchess County?

We have stacks of ready-made holidays and luxury getaways in Dutchess County, and usually the more flexible you can be on dates, the better the deal. Simply enter your travel details and we’ll find you loads of wallet-friendly deals. You can filter by trip length, hotel stars and flight class and – ta-daa – best break ever. Added bonus: our Price Promise refunds the difference if you find a lower price up to 24 hours before check-in.

When is the best time to visit Dutchess County?

usually has the best bargain breaks when hotel prices are often cheaper, and Dutchess County is quieter. But for more of a buzz, plan your visit in .

Why choose Wotif to book your holiday package to Dutchess County?

Plan your trip to Dutchess County today and you could save 40 on your next escape and pay just AU$8,024. With Wotif, you know you’ve got great flexibility and those awesome Mates Rates deals, too.