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.
Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Price was CA $1,263, price is now CA $812 per person
CA $812
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
Elevators could use some work.

Reviewed on Jun 23, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,044, price is now CA $3,150 per person
CA $3,150
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,330, price is now CA $840 per person
CA $840
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,182 reviews)
The rooms are neat and clean. It's a no frills hotel but it has everything you'll need. All the amenities were new and functioned great - AC, TV, lights, furniture, bed, linens. The bath was sparkling clean and recently renovated. Staff is helpful and attentive.

Reviewed on Jun 24, 2026

Library Hotel by Library Hotel Collection

Library Hotel by Library Hotel Collection

4 out of 5
Manhattan
Price was CA $1,761, price is now CA $1,192 per person
CA $1,192
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,007 reviews)
Conveniently located at 41st and Madison, just a block away from Bryant Park, the public library, the 42nd street subway stop and 5th Avenue shopping. The 2nd floor lounge is a quiet spot to reset with complimentary snacks, beverages and fruit. The rooms are typical New York small but cozy with the cute library theme. For those who receive complimentary breakfast at the adjacent Madison & Vine restaurant, the food is fine but the service is inconsistent and slow.

Reviewed on Jun 22, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,113 per person
CA $1,113
per person
Sep 4 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Location is great but No water or coffee available at the hotel . Room has window AC unit that was very loud. The room was very small

Reviewed on Jun 24, 2026

Dutchess County Hotel Deals

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 $175 per night from Jul 2 to Jul 3
CA $175
CA $203 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Nice, spacious room. Comfy bed, fluffy towels. Good breakfast!"

Reviewed on Jun 24, 2026

Hyatt Place Poughkeepsie / Hudson Valley
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 $132 per night from Jul 8 to Jul 9
CA $132
CA $152 total
Jul 8 - Jul 9
includes taxes & fees
8.2/10 Very good! (141 reviews)
"Neat, nice stay, good location."

Reviewed on Jun 24, 2026

Spark by Hilton Fishkill
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 8 to Jul 9
CA $173
CA $203 total
Jul 8 - Jul 9
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"I arrived and was informed that there was no air conditioning or hot water at the hotel. They said they had reached out to other hotels to accommodate their guests. They moved me to a new hotel where I had to book a new room and pay for it out of pocket. They said I would be refunded but then refused ..."

Reviewed on Jun 22, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
See all 404 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 $812, 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.