Dutchess County Holidays & Package Deals 2026

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

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

The Latest Dutchess County Holiday Deals

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

Hotel Riu Plaza New York Times Square

Manhattan

AU$3,405

per person

16 Jan - 26 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to New York (JFK)

9/10 Wonderful! (3,435 reviews)

Excelente servicio, tanto del personal para del ambiente. El desayuno nos encantó un buffet amplio y variado. Y lo más importante la localidad queda cerca de todo. Recomendado al 100%

Reviewed on 31 Oct 2026

Hotel Riu Plaza Manhattan Times Square

Manhattan

AU$5,544

per person

20 Dec - 27 Dec

found 24 hours ago

Return direct flight included

Brisbane (BNE) to New York (JFK)

9.2/10 Wonderful! (4,080 reviews)

The Wall Street Hotel

Manhattan

AU$4,899

per person

16 Jan - 26 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to New York (JFK)

9.8/10 Exceptional! (811 reviews)

The William Hotel Midtown, New York

Manhattan

AU$5,188

per person

20 Dec - 27 Dec

found 24 hours ago

Return direct flight included

Brisbane (BNE) to New York (JFK)

9.4/10 Exceptional! (275 reviews)

Perfect location

Reviewed on 30 Oct 2026

Pendry Manhattan West

Manhattan

AU$8,497

per person

2 Dec - 8 Dec

found 1 day ago

Return flight included

Sydney (SYD) to New York (JFK)

9.8/10 Exceptional! (566 reviews)

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

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

Fully refundableReserve now, pay when you stay

AU$182

29 Nov - 30 Nov

includes taxes & fees

9/10 Wonderful! (1,146 reviews)

"Bbbgfddxcvvvvvvvvvvvvvvvv"

Reviewed on 30 Oct 2026

Comfort Suites Fishkill near Interstate 84

835 Route 52 Fishkill NY

Fully refundable

AU$161

29 Nov - 30 Nov

includes taxes & fees

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

Fully refundableReserve now, pay when you stay

AU$245

9 Nov - 10 Nov

includes taxes & fees

8.2/10 Very good! (1,010 reviews)

"The room we booked was a king room with a sofa bed. No sofa bed in the room. It was also missing a couple of lamps. I know this because our friends booked the same room for the same price and had the sofa and lamps. Toilet paper holder hanging out of the wall.when we first arrived the hallway to ..."

Reviewed on 30 Oct 2026

See all 3,946 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 AU$3,405, 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.

Stay near popular Dutchess County attractions

A wall with various food-related words and phrases, such as 'EAT', 'MUSTARD', 'LEMON', and 'ROAST'.

Culinary Institute of America

9.2/10 (275 reviews)

This prestigious culinary college offers a rare chance to dine at student-run restaurants showcasing future chefs. Reserve a table at The Bocuse Restaurant for modern French cuisine with Hudson River views.

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