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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,162, price is now CA $688 per person
CA $688
per person
Sep 12 - Sep 15
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $3,721, price is now CA $1,910 per person
CA $1,910
per person
Sep 18 - Sep 25
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a steam room, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and Metropolitan Museum of Art are located nearby.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,272, price is now CA $752 per person
CA $752
per person
Sep 12 - Sep 15
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,038, price is now CA $1,807 per person
CA $1,807
per person
Aug 27 - Aug 30
found 8 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Grand Central Terminal are located nearby.
Allegria Hotel

Allegria Hotel

4 out of 5
Price was CA $2,349, price is now CA $1,461 per person
CA $1,461
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this beach hotel in Long Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Long Beach and Long Beach Historical Museum 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 $156 per night
CA $156
CA $181 total
Aug 2 - Aug 3
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 Casperkill Golf Club are located nearby.
Pool
Breakfast included
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 $127 per night
CA $127
CA $146 total
Aug 9 - Aug 10
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 Van Wyck Homestead Museum and Blodgett Memorial Library are located nearby.
Breakfast included
Parking included
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 $160 per night
CA $160
CA $188 total
Jul 26 - Jul 27
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.
Parking included
Free WiFi
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 $214 per night
CA $214
CA $242 total
Jul 12 - Jul 13
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.
Breakfast included
Pet-friendly
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Free cancellation
The price is CA $123 per night
CA $123
CA $143 total
Aug 9 - Aug 10
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.
Breakfast included
Parking included
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Free cancellation
The price is CA $137 per night
CA $137
CA $159 total
Aug 9 - Aug 10
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 helpful staff and the clean rooms in our reviews. Popular attractions Frances Lehman Loeb Art Center and Vassar Golf Course are located nearby.
Pool
Breakfast included
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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 $688, 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.