Poughkeepsie Vacation Packages
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Your Poughkeepsie Vacation
Design your ideal adventure with a Poughkeepsie vacation package tailored to your needs and preferences. Rich history, cultural experiences and spectacular views are just a few of the things that await you in this historic city. Any trip to Poughkeepsie needs a well-designed itinerary. Fill yours with big-name attractions like Marist College, Vassar College and Culinary Institute of America. A couple of clicks is all it takes to create the perfect Poughkeepsie vacation on Expedia.
Top Poughkeepsie Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Where to stay in Poughkeepsie
Find the best Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Poughkeepsie
Poughkeepsie Waterfront
1 out of top 10 points of interest in this area
You'll enjoy the restaurants and riverfront in Poughkeepsie Waterfront. You might want to make time for a stop at Walkway Over the Hudson State Historic Park or Mid-Hudson Bridge.
Arlington
1 out of top 10 points of interest in this area
You'll enjoy the coffeehouses and art galleries in Arlington. You might want to make time for a stop at Frances Lehman Loeb Art Center or Vassar Golf Course.
Crown Heights
Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop.
Downtown Poughkeepsie
2 out of top 10 points of interest in this area
If you're spending some time in Downtown Poughkeepsie, Bardavon 1869 Opera House and Mid-Hudson Civic Center are top sights worth seeing.
Red Oaks Mill
The river views, waterfalls, and breweries are just a few things travelers enjoy about Red Oaks Mill. If you want to experience more of the area, check out Locust Grove or Poughkeepsie Galleria.
Ready to book your vacation to Poughkeepsie?
Poughkeepsie Hotel Deals
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $146
CA $170 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,031 reviews)
"Rude staff"
Reviewed on Aug 9, 2026
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $108
CA $125 total
Sep 9 - Sep 10
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"We have stayed at this hotel before and once again, I was pleased with the location, the friendly staff, and the ample breakfast."
Reviewed on Aug 9, 2026
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $152
CA $178 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
"Good stay with clean amenities."
Reviewed on Aug 8, 2026
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 Poughkeepsie attractions
Eleanor Roosevelt National Historic Site
9.4/10 (111 reviews)
You can find out about the history of Haviland with a stop at Eleanor Roosevelt National Historic Site. While you're in the area, stroll along the riverfront.
Poughkeepsie Bridge
9.2/10 (244 reviews)
You can learn about the history of Poughkeepsie with a trip to Poughkeepsie Bridge. While you're in the area, stroll along the riverfront.
Locust Grove
8.6/10 (63 reviews)
You can browse the exhibits at Locust Grove, a museum with a storied past, during your trip to Poughkeepsie. Stroll along the riverfront or attend a sporting event in the area.
Mid-Hudson Bridge
9.2/10 (235 reviews)
Cycle or walk across this high bridge for panoramic views and see it at night to appreciate its intricate lighting system.
Mid-Hudson Civic Center
8.4/10 (79 reviews)
Mid-Hudson Civic Center is just one of the places to see in Poughkeepsie, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or attend a sporting event in the area.
Bardavon 1869 Opera House
9.2/10 (18 reviews)
Enjoy a performance at Bardavon 1869 Opera House, a theater with a story to tell in Poughkeepsie. Stroll along the riverfront or attend a sporting event in the area.
Clinton House State Historic Site
2.0/10 (1 review)
Find out about the history of Poughkeepsie when you spend time at Clinton House State Historic Site. Amble around the area's riverfront or attend a sporting event.
Casperkill Golf Club
6.0/10 (1 review)
Enjoy a round of golf in Poughkeepsie at Casperkill Golf Club. Amble around the area's riverfront or attend a sporting event.
Frequently asked questions
How much does a Poughkeepsie vacation package cost?
Offering great value package deals from CA $713 on Expedia, you'll be surprised at how little a vacation to Poughkeepsie costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Poughkeepsie?
January, February and March are the best times to search for cheap Poughkeepsie vacation packages. Opting to travel in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Poughkeepsie?
Dedicate at least 2 days for your Poughkeepsie vacation if you want to take in everything that makes this place special. Wander around key areas, including Crown Heights and Spackenkill. Then make a beeline for top sights like Eleanor Roosevelt National Historic Site and Hyde Park Railroad Station. With a clever itinerary, you can keep busy with room for some rest time too. Want to travel beyond Poughkeepsie? Consider an excursion or two.
Is it worth booking a vacation package to Poughkeepsie?
It's no wonder a Poughkeepsie vacation is on the to-do list of many travellers. Leading attractions like Poughkeepsie Bridge are just the start of things to keep you busy here.
How to find the best Poughkeepsie package deals?
Begin your search for a Poughkeepsie package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Poughkeepsie package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Poughkeepsie adventure underway.
Is it cheaper to book a Poughkeepsie vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Poughkeepsie trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Poughkeepsie?
If you're planning a spontaneous Poughkeepsie adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Poughkeepsie?
- Choose when to go: Check your calendar and pack your bags. Your preferred season and the available activities will also help you decide when to visit Poughkeepsie.
- Set a budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Poughkeepsie. Then, pick a property that matches your budget, whether that's a wallet-friendly stay or a high-end getaway.
- Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to experience in Poughkeepsie. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Poughkeepsie vacation package that brings all your bookings together.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
