Poughkeepsie Vacations from $169

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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.

The Latest Poughkeepsie vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
Price was $238, price is now $169 per person
$169
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
The stay was excellent. The pool was a perfect temp for all to unwind after a long drive. We enjoyed the breakfast. The staff was very friendly and helpful.

Reviewed on Dec 2, 2025

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2 out of 5
Southeast Yonkers
Price was $1,031, price is now $681 per person
$681
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
No reviews
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
Price was $432, price is now $296 per person
$296
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
8.4/10 Very Good! (1,012 reviews)
Everything was good!!!

Reviewed on Dec 1, 2025

Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
Save 100% on your flight
Price was $527, price is now $364 per person
$364
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to White Plains (HPN)
8/10 Very Good! (1,001 reviews)
Loved the Gym and Pool.

Reviewed on Dec 2, 2025

Sleepy Hollow Hotel

Sleepy Hollow Hotel

3.5 out of 5
Save 100% on your flight
Price was $530, price is now $374 per person
$374
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to White Plains (HPN)
6.8/10 (1,002 reviews)
Room is great except the heating system doesn’t hold the temperature setting.

Reviewed on Dec 2, 2025

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Where to stay in Poughkeepsie

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

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 with a trip to Poughkeepsie Bridge. While you're in the area, stroll along the riverfront.

Poughkeepsie Bridge

Vassar College

Take a campus tour or just explore the area of Vassar College, during your travels in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.

Vassar College

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
See all activities in Poughkeepsie

Poughkeepsie Hotel Deals

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Dec 12 to Dec 13
$115 total
Dec 12 - Dec 13
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Comfortable room

Reviewed on Nov 30, 2025

Hampton Inn & Suites Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $127 total per night from Dec 3 to Dec 4
$127 total
Dec 3 - Dec 4
Total with taxes and fees
8.8/10 Excellent! (1,021 reviews)
Lovely property, wonderful staff will definitely return back.

Reviewed on Dec 2, 2025

Hyatt Place Poughkeepsie / Hudson Valley
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Fully refundable
$95 nightly
The price is $111 total per night from Dec 7 to Dec 8
$111 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (1,017 reviews)
The room was very nice especially the shower. I stayed at a huge variety of hotels and I never had a shower as good was what they had. By far a very relaxing experience. Smooth check in and check out process and front desk staff was very accommodating!

Reviewed on Nov 30, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 2,470 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.

Find the Best Poughkeepsie Vacation Packages

Poughkeepsie Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
30,400
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
SplashDown Beach, Chance Theater and James Baird State Park

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Frequently asked questions

How much does a Poughkeepsie vacation package cost?
You'll find cheap prices from $169 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.

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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.