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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,547, price is now CA $1,033 per person
CA $1,033
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,931 reviews)
The staff were terrific,, accessible and welcoming... Rooms were kept so clean. Staff at the breakfast buffet were gracious and helpful... Great location... Will be back... Michael & Sarah C.

Reviewed on Mar 26, 2026

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3 out of 5
Southeast Yonkers
Price was CA $3,444, price is now CA $2,032 per person
CA $2,032
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
7.2/10 Good! (5 reviews)
This was an excellent House My birthday weekend was amazing I totally would book again

Reviewed on Mar 17, 2024

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was CA $3,051, price is now CA $1,979 per person
CA $1,979
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,006 reviews)
Very quiet hotel in the heart of manhattan. Lovely rooms that were quite large by NYC standards. Bed was comfortable. Room well appointed. Could use more thoughtful lighting in areas where you unpack luggage, and lobby bar closure a little disappointing. However the breakfast was absolutely excellent and the evening appetizer and cocktail time a very nice addition to the stay. Definitely a hidden gem! Would for sure stay again.

Reviewed on Mar 21, 2026

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Price was CA $1,861, price is now CA $1,213 per person
CA $1,213
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (32 reviews)
The room was very clean and staff super friendly! Recommended!

Reviewed on Mar 20, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,748, price is now CA $3,748 per person
CA $3,748
per person
May 31 - Jun 5
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,000 reviews)
Excellent staff, clean room, fantastic onsite restaurants.

Reviewed on Mar 10, 2026

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 CA $160 per night from Apr 22 to Apr 23
CA $160
CA $186 total
Apr 22 - Apr 23
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Clean room with comfortable bed and nice bathroom. Friendly staff.

Reviewed on Mar 23, 2026

Hampton Inn & Suites Poughkeepsie
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

3 out of 5
17 Westage Drive Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Mar 30 to Mar 31
CA $165
CA $186 total
Mar 30 - Mar 31
includes taxes & fees
8.8/10 Excellent! (760 reviews)
Staff was very nice . Gave us water bottles , and i loved that they didn’t come knocking on the door as soon as it was checkout time

Reviewed on Mar 18, 2026

Courtyard by Marriott 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 $152 per night from Mar 30 to Mar 31
CA $152
CA $176 total
Mar 30 - Mar 31
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
OK

Reviewed on Mar 24, 2026

Hyatt Place Poughkeepsie / Hudson Valley
See all 3,888 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 $1,033, 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.