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.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

Southeast Yonkers
CA $981
per person
Dec 11 - Dec 14
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
3.6/10 (4 reviews)
LIARS! these people take your money, when you go check in you'll find they aren't the real hosts. and house is already rented long term. NOT A TRUE LISTING!

Reviewed on Oct 14, 2026

Upscale Modern Luxury 3BR Home

Upscale Modern Luxury 3BR Home

CA $1,937
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
4/10 (1 review)
Property was missing needed items and it took two days to get them(coffee maker). For the price you get what you’d expect. Older property with some updates needed. Everything worked but older appliances.

Reviewed on Jan 23, 2026

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking

Bryn Mawr
CA $2,440
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to White Plains (HPN)
No reviews
This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!

Reviewed on Oct 12, 2026

Hyatt Regency Greenwich

Hyatt Regency Greenwich

CA $1,459
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to White Plains (HPN)
8.8/10 Excellent! (1,155 reviews)
Loved this hotel- it was clean, had lots of amenities, and our room was very modern and well-decorated. Staff was helpful, welcoming, and kind, and room service was also quick. The only critiques were that we could hear almost everything happening in the hallway (so if you're a light sleeper, this would not be a great hotel for you) and it also felt somewhat frustrating to be charged to park in the very large lot that required a significant walk to the hotel and was not well-lit. Overall, would recommend with those caveats.

Reviewed on Oct 21, 2026

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

Save 100% on your flight
CA $4,639
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
8/10 Very good! (1 review)
Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine.

Reviewed on Nov 8, 2025

Where to stay in Poughkeepsie

Find the best Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Poughkeepsie
A nighttime view of a bridge with colorful lights reflecting on the water.

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.

Find hotels in Arlington
A marina with several boats docked at sunset.

Poughkeepsie Waterfront

2 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.

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A large suspension bridge spanning a river, surrounded by dense greenery.

Crown Heights

Visitors to Crown Heights enjoy its coffeehouses, and if you want to do some exploring, Hudson River is worth a stop.

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A historic stone building with a sign reading "The Old Newspaper Building."

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.

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A suspension bridge over a river, surrounded by autumn foliage and urban buildings.

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.

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Ready to book your vacation to Poughkeepsie?

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Poughkeepsie Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $132
CA $153 total
Nov 22 - Nov 23
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY
Fully refundable
CA $111
CA $129 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Excellent place—nice room and fine breakfast"

Reviewed on Oct 21, 2026

Holiday Inn Express Poughkeepsie by IHG
The Heartwood

The Heartwood

165 College Avenue Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $237
CA $276 total
Nov 16 - Nov 17
includes taxes & fees
The Heartwood
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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.
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Stay near popular Poughkeepsie attractions

A suspension bridge over a river with a forested hillside in the background.

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.
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A steel bridge over a body of water with autumn foliage in the background.

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.
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A large, stately building with a symmetrical facade, stone detailing, and green shutters.

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.
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A large brick house with green shutters, surrounded by a grassy field and large trees.

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.
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A lit bridge with a cross on top and a church with a steeple in the foreground.
Photo by Gregg Tobias

Chance Theater

8.0/10 (70 reviews)
Enjoy a show at Chance Theater, a storied theater in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.
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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.
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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.
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McCann Arena

Catch an event at McCann Arena during your trip to Poughkeepsie. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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Frequently asked questions

How much does a Poughkeepsie vacation package cost?
Offering great value package deals from CA $981 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.