Dutchess County Vacation Packages

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Your Dutchess County Vacation

Choose a vacation 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 vacation is only clicks away with Expedia.

Top vacation destinations in Dutchess County

FlightsFlightsHotelsHotels

Poughkeepsie

Poughkeepsie
FlightsFlightsHotelsHotels

Rhinebeck

Rhinebeck

Top Dutchess County Vacation Deals

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

The Wayne Inn

2 out of 5
Price was CA $1,422, price is now CA $668 per person
CA $668
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to New York (JFK)
6.8/10 (289 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was CA $3,975, price is now CA $2,103 per person
CA $2,103
per person
Jul 10 - Jul 12
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $2,403, price is now CA $1,298 per person
CA $1,298
per person
Jul 1 - Jul 5
found 13 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.4/10 Exceptional! (4,384 reviews)
We’ll definitely definitely be staying there again! Very beautiful hotel, and it has a Starbucks on the first floor!

Reviewed on May 7, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $3,347, price is now CA $2,010 per person
CA $2,010
per person
Jul 25 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,979 reviews)
Lots of hot and cold options for breakfast. Hotel bar was nice and the food was good. Bartender was great. Rooms were comfortable.

Reviewed on May 10, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,941, price is now CA $1,789 per person
CA $1,789
per person
Jul 25 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,482 reviews)
Every thing was good

Reviewed on May 8, 2026

Dutchess County Hotel Deals

Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jun 7 to Jun 8
CA $122
CA $141 total
Jun 7 - Jun 8
includes taxes & fees
8/10 Very Good! (85 reviews)
Stayed one night the bed was very comfortable.

Reviewed on May 9, 2026

Spark by Hilton Fishkill
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 CA $162 per night from May 26 to May 27
CA $162
CA $188 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
Nice place comfortable room friendly staff

Reviewed on May 9, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from May 31 to Jun 1
CA $109
CA $127 total
May 31 - Jun 1
includes taxes & fees
6.6/10 (1,023 reviews)
I am still working to get a security deposit charged twice credited back to my charge card. The price of the room was great for the area. The rooms were decent though I needed to clean a coffee pot given to me for the room by myself. The hotel is very dated. I will not stay there again.

Reviewed on May 9, 2026

Studio 6 Extended Stay Fishkill Route 9 NY
See all 405 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Dutchess County vacation package cost?
Our Dutchess County packages, which start from as low as CA $668, are the perfect way to save. Handpick your favorite 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 vacation 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 vacation 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 travelers.
How far in advance should I book my Dutchess County vacation?
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 vacation. 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 vacation 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 vacation rentals like beach villas and spacious residences. The list goes on!
Can I choose my airline with a Dutchess County Expedia vacation 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 vacation package?
If your vacation 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.