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

Poughkeepsie featuring autumn leaves and a river or creek
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Poughkeepsie

Poughkeepsie
Rhinebeck featuring a city
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Rhinebeck

Rhinebeck

Top Dutchess County Vacation Deals

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

Night Hotel Broadway

2.5 out of 5
Manhattan
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7/10 Good! (2,245 reviews)
The location is ideal for how I like to stay in New York. The overall rating is low because the doorman stayed on his phone, I had to get and use the luggage rack myself while the bellboy helped the desk clerk (Justin) who had to be prompted for information on parking, early check out, etc. He needs a review course in hospitality.

Reviewed on Aug. 3, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 20 - Oct 23
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Staff was super helpful, i enjoyed the walkable distance to many different things.

Reviewed on Jul. 31, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,897 reviews)
Great location - courteous staff.

Reviewed on Aug. 1, 2025

Dutchess County Hotel Deals

Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Aug 17 to Aug 18
CA $143
CA $162 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (458 reviews)
"Would go back"

Reviewed on Jul. 30, 2025

Wingate by Wyndham Fishkill
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $175 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on Aug. 1, 2025

Holiday Inn Express Poughkeepsie by IHG
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Sep 1 to Sep 2
CA $222
CA $251 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (370 reviews)
"We had a nice two-night stay on our way to a family event in Massachusetts. Food and drink were excellent. Bar/restaurant area gets very loud on a Friday evening. Free breakfast was great. Room was spacious! Would have been nice to have a pool on hot July days."

Reviewed on Jul. 31, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 427 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
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Frequently asked questions

How much does a Dutchess County vacation package cost?
Our Dutchess County packages, which start from as low as CA $764, 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.