Poughkeepsie Vacations from $317

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Poughkeepsie vacation packages

Price found within the past 48 hours. Click for updated prices.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.6/10 Excellent! (1,000 reviews)
I was shocked when at 10.57am my room card was blocked!!! I was ready to pick up my bags and proceed to check out at 11am, but was unable to enter my room. I called downstairs and was told that now I must come to the lobby and present my ID!!! I wanted to make a official complaint to the manager, but the clerk at registration said she "is busy". Finally I was given a master key and was able to get my belongings. This kind of service is terrible. They charge $250 for night and check you out without your knowledge at 10.57am!!!

Reviewed on Aug 15, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 14
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8/10 Very Good! (463 reviews)
I liked that it was quiet I didn’t like that there was no guidance for the cycling trails o walking trails given

Reviewed on Aug 6, 2025

The Stamford Hotel

The Stamford Hotel

3.5 out of 5
Downtown Stamford
Save 100% on your flight
per person
Oct 29 - Nov 2
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
7.8/10 Good! (1,088 reviews)
Enjoy my stay each time

Reviewed on Aug 15, 2025

Global Luxury Suites White Plains

Global Luxury Suites White Plains

3.5 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 2
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
6.8/10 (31 reviews)
Nice view from the apartment and great for business trip.

Reviewed on Dec 16, 2024

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
Save 100% on your flight
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8/10 Very Good! (1,092 reviews)
Room is clean Bed is comfortable Staff are friendly I’d stay here again

Reviewed on Aug 17, 2025

Don't see what you're looking for?
See all available trips from Columbus to Poughkeepsie
View all trips

Where to stay in Poughkeepsie

Find the best Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Poughkeepsie
Default Image

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 Overlook Drive-In Theater or Frances Lehman Loeb Art Center.

Find hotels in Arlington

Discover the most popular places to visit in Poughkeepsie

Mid-Hudson Bridge which includes a bay or harbor, a bridge and a river or creek

Mid-Hudson Bridge

Cycle or walk across this high bridge for panoramic views and see it at night to appreciate its intricate lighting system.

Mid-Hudson Bridge
Longest footbridge in the world....as viewed from Water Street.

Poughkeepsie Bridge

You can learn about the history of Poughkeepsie Waterfront with a trip to Poughkeepsie Bridge. While you're in the area, stroll along the riverfront.

Poughkeepsie Bridge
Looking south at the Poughkeepsie bridge.

Chance Theater

4/5(17 reviews)

Enjoy a show at Chance Theater, a storied theater in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.

Chance Theater

What to do in Poughkeepsie

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

$48
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

$67
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

$159
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
See all activities in Poughkeepsie

Poughkeepsie Hotel Deals

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Sep 9 to Sep 10
$120 total
Sep 9 - Sep 10
Total includes taxes and fees
7.6/10 Good! (389 reviews)
"Room was clean and neat. Breakfast had limited options but was good enough. Staff was very friendly and professional. Will stay again should my business bring me back this way."

Reviewed on Aug 11, 2025

Quality Inn Poughkeepsie
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
$109 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Pro tip: room away from elevators"

Reviewed on Aug 13, 2025

Holiday Inn Express Poughkeepsie by IHG
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $133 total per night from Aug 21 to Aug 22
$133 total
Aug 21 - Aug 22
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"The property was clean and comfortable. The room was spacious and the beds were comfortable. We enjoyed the bar and the morning coffee was hot and delicious."

Reviewed on Aug 15, 2025

DoubleTree by Hilton Poughkeepsie Convention Center
See all 2,479 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Poughkeepsie vacation package cost?
You'll find cheap prices from $317 on Expedia for your Poughkeepsie escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Poughkeepsie costs.
What are the cheapest months to go to Poughkeepsie?
You can usually find reduced prices and greater availability in January, October and December. Check out our cheap Poughkeepsie vacation packages and you could score some great off-season deals.
How many days is enough for Poughkeepsie?
We'd suggest booking a Poughkeepsie vacation for around 2 days. This will give you plenty of time to visit popular sights such as Poughkeepsie Bridge and Eleanor Roosevelt National Historic Site, and explore neighborhoods like Arlington and Red Oaks Mill. You could even make time for a day trip from Poughkeepsie.
Is it worth booking a vacation package to Poughkeepsie?
Poughkeepsie is a good vacation destination with attractions like Walkway Over the Hudson State Historic Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Poughkeepsie vacation promises fun for everyone.
How to find the best Poughkeepsie package deals?
Landing a cheap Poughkeepsie package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Poughkeepsie package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Poughkeepsie vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Poughkeepsie vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Poughkeepsie?
If you've got your Poughkeepsie travel dates locked in, book early to bag some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Poughkeepsie?

  1. Pick your dates: What you want to do in Poughkeepsie and your preferred season will help you decide when to go.
  2. Set a budget: Factor in costs such as flights, transportation and food when calculating how much to save for your trip to Poughkeepsie. Then, select a hotel that suits your budget, whether that's an economical stay or a deluxe getaway.
  3. Use our trip planning tool to discover Poughkeepsie: Research every aspect of your trip to Poughkeepsie with this comprehensive planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Think about how much time you'd like to spend exploring Poughkeepsie. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  5. 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.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Browse some of the exciting things to do in Poughkeepsie and reserve your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Poughkeepsie vacation packages?
Jet off on your ideal getaway to Poughkeepsie with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until the next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.