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
Save 100% on your flight
CA $948
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to White Plains (HPN)
3.6/10 (4 reviews)
It took calling the booking website customer service to get in contact with the host. I end up getting a different property that the one I reserved but the new on was more bedrooms, at the end I work out but it took some long coy with the host.

Reviewed on Jun 29, 2026

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

Save 100% on your flight
CA $1,266
per person
Oct 29 - Nov 2
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.

Reviewed on Feb 11, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

Save 100% on your flight
CA $1,243
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)
This hotel, and its staff, was amazing! The restaurant was exceptional! Will definitely stay here again!

Reviewed on Sep 22, 2026

The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

CA $1,219
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
9.2/10 Wonderful! (578 reviews)
Amazing. Loved this hotel.

Reviewed on Sep 21, 2026

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

Downtown Rochelle
CA $1,010
per person
Nov 14 - Nov 17
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to White Plains (HPN)
8.4/10 Very good! (1,078 reviews)
Not bad, just okay

Reviewed on Sep 21, 2026

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 Poughkeepsie Bridge or Walkway Over the Hudson State Historic Park.

Find hotels in Poughkeepsie Waterfront
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.

Find hotels in Downtown Poughkeepsie
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.

Find hotels in Red Oaks Mill

Ready to book your vacation to Poughkeepsie?

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Poughkeepsie Hotel Deals

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY
CA $136
CA $158 total
Oct 21 - Oct 22
includes taxes & fees
Quality Inn Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY
CA $154
CA $179 total
Oct 21 - Oct 22
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 $136
CA $158 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Very nice staff and very helpful. Clean and spacious rooms."

Reviewed on Sep 22, 2026

Holiday Inn Express Poughkeepsie by IHG
See all 2,523 properties in Poughkeepsie
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 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 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 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 marina with various boats docked, a large suspension bridge in the background, and a forested hillside.

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 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 Ice Arena

2.0/10 (1 review)
You can take time to visit McCann Ice Arena during your travels to Poughkeepsie. Stroll along the riverfront or attend a sporting event in the area.
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What to do in Poughkeepsie

Hallows and Hauntings of Hyde Park Ghost Tour

Hallows and Hauntings of Hyde Park Ghost Tour

CA $45
per adult
Hallows and Hauntings of Hyde Park Ghost Tour
See all activities in Poughkeepsie

Frequently asked questions

How much does a Poughkeepsie vacation package cost?
Offering great value package deals from CA $948 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.