Poughkeepsie Vacations from $442

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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.
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
Price was $558, price is now $442 per person
$442
per person
Jan 15 - Jan 18
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
8.8/10 Excellent! (1,193 reviews)

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

4 out of 5
Price was $2,156, price is now $1,567 per person
$1,567
per person
Dec 16 - Dec 23
found 23 hours ago
Roundtrip flight included
San Juan (SJU) to White Plains (HPN)
2/10 (3 reviews)
It was a scam the house was never a villa and someone lives there they lied and are scammers

Reviewed on Oct 25, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
Price was $1,227, price is now $975 per person
$975
per person
Jan 20 - Jan 24
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to White Plains (HPN)
9.4/10 Exceptional! (1,002 reviews)

Days Inn by Wyndham Elmsford / White Plains

Days Inn by Wyndham Elmsford / White Plains

2 out of 5
Price was $776, price is now $630 per person
$630
per person
Dec 18 - Dec 23
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
7.4/10 Good! (1,013 reviews)

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

2 out of 5
Price was $793, price is now $647 per person
$647
per person
Jan 9 - Jan 13
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to White Plains (HPN)
2/10 (1 review)
The place was not accurate and likely a scam. The listing should be removed. We arrived at the location with no real instructions on how to access the space, phone number on the listing was not an active number. We asked for our money back and still waiting for it. DONT STAY OR RESERVE THIS LOCATION. It's likely a scam!

Reviewed on Oct 27, 2026

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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
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

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)
This engineering marvel spans the Hudson River with steel suspension elegance. Stroll the pedestrian path while experiencing "Bridge Music," a unique sound-art installation transforming the structure into an instrument.
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Poughkeepsie Hotel Deals

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
$105 nightly
The price is $122 total per night from Nov 11 to Nov 12
$122 total
Nov 11 - Nov 12
Total with taxes and fees
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
$91 nightly
The price is $106 total per night from Nov 29 to Nov 30
$106 total
Nov 29 - Nov 30
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG
The Heartwood

The Heartwood

3.5 out of 5
165 College Avenue Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $194 total per night from Nov 30 to Dec 1
$194 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (349 reviews)
"Excellent, helpful staff and amenities. The room was spotless & very comfortable. The hotel restaurant was top notch: service & the quality of cuisine were also excellent."

Reviewed on Oct 29, 2026

The Heartwood
See all 2,542 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

Things to do in and around Poughkeepsie

Poughkeepsie offers a delightful mix of outdoor and family-friendly activities perfect for an adventure-filled vacation. Enjoy holiday events and festivals, explore nearby attractions, and unwind in beautiful picnic areas. The city also boasts a vibrant shopping scene and rich cultural experiences, making it an ideal destination for tourists seeking both recreation and relaxation.

Shopping

The Poughkeepsie Galleria, located 6 miles away, offers a vibrant shopping experience with various stores and entertainment options. If you're up for a drive, visit the Hudson Valley Mall, 18 miles away, for even more shopping and family-friendly activities. The Stormville Airport Antique Show & Flea Market, 13 miles away, is perfect for unique finds.

Recreation

At the Overlook Drive-In Theater, enjoy a nostalgic movie experience under the stars with family-friendly films that evoke a sense of romance and entertainment. For golf enthusiasts, Casperkill Golf Club offers a scenic outdoor setting to perfect your swing while soaking in the fresh air.

Adventure

Experience thrills at SplashDown Beach, an exciting waterpark located 11 miles from Poughkeepsie, perfect for family fun. For arcade enthusiasts, Fun Central offers adventure vibes 7 miles away. Enjoy outdoor camping and adventure at North Landing Beach, situated 9 miles from Poughkeepsie.

Nightlife

Poughkeepsie's nightlife offers a vibrant mix of bars and music venues. Check out The Chance Theater for live shows, or unwind at The Hairy Lemon for a cozy pub atmosphere. For a fun dance scene, visit The Poughkeepsie Grind, where you can enjoy great drinks and local DJs.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Poughkeepsie

Poughkeepsie, New York, offers a perfect blend of outdoor adventures and family-friendly activities, making it an ideal vacation spot. Visitors can explore local attractions like the Poughkeepsie Galleria, the historic Poughkeepsie Bridge, and the scenic waterfront. Whether you're seeking cultural experiences or thrilling adventures, this charming city has something for everyone to enjoy.

  • Vassar College: Experience the vibrant atmosphere of this modern college, known for its stunning architecture and beautiful campus. Take a stroll through its gardens, admire the art galleries, and soak in the intellectual energy that radiates from this prestigious institution.
  • Culinary Institute of America: Delve into the world of culinary arts at this historic college, located just 3 miles away. Enjoy exquisite dining experiences at its restaurants and witness future chefs honing their skills in a rich cultural setting that celebrates food and creativity.
  • Walkway Over the Hudson State Historic Park: Enjoy breathtaking views from this historic bridge, just 1 mile away. This elevated park offers scenic walking and biking trails, providing a unique opportunity to appreciate the majestic Hudson River and its surroundings.

Best time to go to Poughkeepsie

The best time to visit Poughkeepsie is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.5°F (-2.5°C)Light RainMostly SunnySlightly LowSlightly Low
February29.3°F (-1.5°C)Light RainMostly SunnySlightly LowSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnySlightly LowSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageSlightly High
June67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
July73.8°F (23.2°C)Light RainMostly SunnySlightly HighAverage
August71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly High
September64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
October53.6°F (12.0°C)Light RainMostly SunnySlightly HighSlightly High
November41.5°F (5.3°C)Light RainMostly SunnyAverageAverage
December33.4°F (0.8°C)Light RainMostly SunnyAverageAverage

Tips to save on your trip to Poughkeepsie

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Poughkeepsie.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Poughkeepsie.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What types of vacation packages are available in Poughkeepsie?
Poughkeepsie, an outdoor and nature destination known for family-friendly attractions, offers vacation packages tailored to several travel styles:
  • Budget package: Quality Inn Poughkeepsie: offers a more affordable stay, with rooms around $150 per night, and includes free breakfast and an indoor pool.
  • Breakfast-included package: Homewood Suites by Hilton Poughkeepsie: rated 8.9 out of 10 by travelers, this hotel provides free breakfast and kitchenettes, making it convenient for longer stays.
  • Pet-friendly package: The Heartwood: a 3.5-star property rated 9.5 out of 10 by travelers, welcomes pets and offers a restaurant and bar/lounge.
  • Family package: Hampton Inn & Suites Poughkeepsie: rated 8.7 out of 10 by travelers, features family rooms and an indoor pool, providing comfort for those traveling with children.
  • Parking-included package: DoubleTree by Hilton Poughkeepsie Convention Center: a 4-star hotel rated 8 out of 10 by travelers, is praised for its great parking facilities, along with a restaurant and free breakfast.
How can I save money on a Poughkeepsie vacation package?
When you bundle, you can save up to 30%*. To save money on a Poughkeepsie package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
How much does a Poughkeepsie vacation package cost?
A Poughkeepsie vacation package typically costs around $800 per adult for a weekend trip. Lower-priced options start around $450 per adult, while premium packages can reach up to $1,650.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Poughkeepsie vacation package deals?
The cheapest Poughkeepsie vacation package deals can be as low as around $370 per adult for weekend trips. Separately, April typically has the lowest average monthly prices, around $670 per adult, for a 3-day trip, while August follows at around $1,040 per adult, for a 4-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — nearly all Poughkeepsie packages include some savings versus booking separately, typically around $30 per adult. Longer, week-long trips can save even more, often around $50 per adult. Browse cheap vacation packages in Poughkeepsie on Expedia for current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Poughkeepsie?
The best time to go for a Poughkeepsie vacation package is during its peak booking months of April, August, and November. April stands out as a particularly good option, as it is also typically the most affordable month for packages, making it a popular choice for value-conscious travelers.
What's included in a Poughkeepsie vacation package?
A Poughkeepsie vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels in Poughkeepsie offer free breakfast, providing a convenient start to your day. Some properties also provide airport shuttle services, which can be helpful for transfers from airports like John F. Kennedy International Airport (JFK).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Poughkeepsie?
Families can build a Poughkeepsie vacation package around a stay at Hampton Inn & Suites Poughkeepsie, rated 8.7 out of 10 by travelers. This hotel offers family rooms and an indoor pool, making it a comfortable base, with travelers often praising the welcoming staff and good value for money in the rooms.

For couples, The Heartwood, a 3.5-star property rated 9.5 out of 10, provides a thoughtful stay with its bar/lounge and restaurant, with guests highlighting the beautiful location and thoughtful rooms.

Travelers seeking a budget-friendly Poughkeepsie vacation package might consider Quality Inn Poughkeepsie, which offers rooms around $150 per night. This hotel includes free breakfast and an indoor pool, with guests noting the nice rooms and clean pool.

*Package availability and prices may change depending on dates and demand.
Is Poughkeepsie a good choice for a family vacation package?
Poughkeepsie is a good choice for family vacation packages, with some bookings being family trips. Hotels like Hampton Inn & Suites Poughkeepsie, rated 8.7 out of 10 by travelers, offer family rooms and indoor pools, providing comfortable stays for those traveling with children.

For activities, families can visit Bowdoin Park, about 3 miles from central Poughkeepsie, which offers outdoor space for recreation. The Poughkeepsie Galleria, also about 3 miles from central Poughkeepsie, provides shopping and entertainment options.
What is the best time to book a Poughkeepsie vacation package?
Book your Poughkeepsie vacation package around 4 weeks in advance. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 8 weeks out.

April, August, and November are the most popular months for Poughkeepsie packages, so booking earlier is advisable if you're traveling during those times.
What are the top things to do in Poughkeepsie?
A Poughkeepsie vacation offers a mix of historical sites, scenic outdoor experiences, and cultural attractions:

Browse and book things to do in Poughkeepsie on Expedia.
How many days do you need for a Poughkeepsie vacation?
Most Poughkeepsie vacation packages last around 3 days, making it ideal for a weekend getaway. This duration allows travelers to experience key attractions like the Walkway Over the Hudson State Historic Park, the Franklin D. Roosevelt Presidential Library and Museum, and the Culinary Institute of America. While most travelers opt for weekend trips, nearly a third choose week-long trips to explore the region more deeply.
Is Poughkeepsie a good destination for a weekend vacation?
Poughkeepsie is an excellent choice for a weekend vacation package. Most travelers choose weekend trips for their Poughkeepsie vacation, having ample time to explore key attractions. A 1-to-3-day trip allows you to visit the Walkway Over the Hudson State Historic Park, explore the Culinary Institute of America, and delve into history at the Franklin D. Roosevelt Presidential Library and Museum.
Do you need to rent a car in Poughkeepsie, or is public transport enough?
For Poughkeepsie vacation packages with flights, a rental car generally offers the most flexibility to explore the wider Hudson Valley region. The nearest major airports include John F. Kennedy International Airport (JFK) and Newark Liberty International Airport (EWR).

Within Poughkeepsie, Dutchess County Public Transit provides local bus service, with a main hub at Main and Market streets, near the Mid-Hudson Civic Center. For regional travel, Metro-North Railroad offers commuter rail service to New York City, and Amtrak also serves the Poughkeepsie station. However, given Poughkeepsie's character as an outdoor and nature destination outside the city, a car is beneficial for reaching attractions like Walkway Over the Hudson State Historic Park and other natural sites that may be spread out.
Are Poughkeepsie vacation package hotels conveniently located?
Poughkeepsie vacation package hotels are generally well-located, offering options both close to the center and slightly further out.

The Heartwood is about 2 miles from central Poughkeepsie, while Homewood Suites by Hilton Poughkeepsie is about 3 miles away. For those preferring to be a bit further out, Hyatt Place Poughkeepsie / Hudson Valley is about 5 miles from central Poughkeepsie. Staying closer to central Poughkeepsie offers easier access to downtown attractions, while properties a bit further out provide convenient access to major routes and other area sights.
Can I change or cancel my Poughkeepsie vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Poughkeepsie vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Poughkeepsie vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Poughkeepsie vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Poughkeepsie?
To find last-minute vacation packages to Poughkeepsie, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Poughkeepsie vacation packages?
Free cancellation on a Poughkeepsie vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Poughkeepsie vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Poughkeepsie getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Poughkeepsie vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.