Book Exclusive Dutchess County Vacation Packages

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Search vacation packages deals in Dutchess County's top destinations

A busy street with parked cars, pedestrians, and outdoor seating at a restaurant.

Rhinebeck

Vacations
Rhinebeck
A suspension bridge over a river, surrounded by lush green hills.

Wappingers Falls

Vacations
Wappingers Falls

Dutchess County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,556, price is now CA $1,545 per person
CA $1,545
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,044, price is now CA $3,372 per person
CA $3,372
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in Brooklyn. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Pendry Natirar

Pendry Natirar

5 out of 5
Price was CA $4,111, price is now CA $2,450 per person
CA $2,450
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this luxury hotel in Far Hills. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Popular attractions Natirar Park and Moorland Farms are located nearby.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,719, price is now CA $1,644 per person
CA $1,644
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was CA $3,201, price is now CA $1,937 per person
CA $1,937
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Wall Street and Brooklyn Bridge are located nearby.

Top Dutchess County hotels deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $147 per night
CA $147
CA $171 total
Aug 20 - Aug 21
includes taxes & fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SplashDown Beach and Bananas Comedy Club are located nearby.
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Free cancellation
Reserve now, pay when you stay
The price is CA $185 per night
CA $185
CA $210 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Starr Library and Dutchess County Fairgrounds are located nearby.
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $158 per night
CA $158
CA $185 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions McCann Ice Arena and Cunneen-Hackett Cultural Center are located nearby.
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $139 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Locust Grove and McCann Golf Course are located nearby.
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Free cancellation
Reserve now, pay when you stay
The price is CA $131 per night
CA $131
CA $151 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SplashDown Beach and Van Wyck Homestead Museum are located nearby.
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
Free cancellation
Reserve now, pay when you stay
The price is CA $234 per night
CA $234
CA $265 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Richard L. Skimin Memorial Baseball Field and Home of Franklin D. Roosevelt National Historic Site are located nearby.
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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.

Stay near popular Dutchess County attractions

A grassy field with a brick wall and a large tree with autumn leaves.

Bard College

8.6/10 (100 reviews)
Enjoy the collegiate vibe at Bard College during your visit to Annandale-on-Hudson. Stroll along the marina or experience the area's festivals.
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Photos of local treasures

Browse Dutchess County vacation photos for more inspiration

A large, historic building with a symmetrical facade, green shutters, and a central entrance with steps leading up to it.
A large suspension bridge spanning a wide river, surrounded by hills and a train track running parallel to the riverbank.
A wooden boardwalk through a field of tall grasses with a bench on the side.
A large, historic building with classical architecture, surrounded by snow.
A wooden boardwalk through a field of tall grasses.

Frequently asked questions

How much are vacation packages to Dutchess County?
Starting as low as CA $1,545, flight and hotel packages are a fabulous way to stretch your vacation budget even further. Get ready Dutchess County — here you come!
Where can I get the best vacation package deals for Dutchess County?
Picking up the perfect package deal to Dutchess County is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 properties around the world, you're flush with choice when selecting your hotels and flights.
Why should I purchase my Dutchess County vacation package via Travelocity?
You'll not only enjoy great savings, but you can also access our 24/7 customer support, excellent service and a Price Match Guarantee. Wander across the globe, uncover lesser-known sights and create lifelong memories — we'll take care of the little details.
Can I save money on my Dutchess County car rental if I bundle it with my hotel or flight?
Definitely. And our Dutchess County vacation packages will help you do it. With only a few clicks you can save money as well as time by booking everything in one place. Pick up the keys to your rental car then set your own course. Need to fill your itinerary? Add a few tours to your package and save on those too.
Which airport is best for Dutchess County?
Bradley Intl. Airport (BDL) is a great option for people jetting into Dutchess County. Tweed - New Haven Regional Airport (HVN) and Stewart Intl. Airport (SWF) also welcome a lot of flights to the region.
What is there to do in Dutchess County?
A vibrant and inspiring destination, Dutchess County is home to some terrific things to see and do. Culinary Institute of America and Marist College are just two of the local highlights.