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Poughkeepsie Vacation Packages

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Top Poughkeepsie vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Aug 27 - Aug 30

    The Prince Kitano New York + Flight

    Manhattan
    3 nights
    4.5 star property
    9.4/10 - Exceptional (2,303 reviews)
    Roundtrip • Toronto (YTZ) - New York (JFK)
    YTZ - EWR • Nonstop EWR - YTZ • Nonstop
    CA $1,433
    CA $942
    per traveller
    found 2 days ago
    The Prince Kitano New York
  • Meeting facility
    Sept 15 - Sept 19

    Radio Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,497 reviews)
    "The overall experience was good however it was negatively impacted by the inaccessibility of their main amenity; the restaurant on the premises. On Thursday 7.16.25 the restaurant was closed 2.5 hrs early due to a private event and the hotel failed to adequately inform it's guests. I explicitly stayed at the Hotel due to a medical condition that was being impacted by the extreme weather (smoky conditions), and, the onsite restaurant was a medical necessity. Apparently there is an internal..."
    Reviewed July 22, 2026
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - LGA • 1 stop LGA - YHM • 1 stop
    CA $1,874
    CA $1,056
    per traveller
    found 1 day ago
    Radio Hotel
  • Front of property
    Sept 3 - Sept 7

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    4 nights
    4.0 star property
    9.0/10 - Wonderful (3,236 reviews)
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - EWR • 1 stop EWR - YHM • 1 stop
    CA $2,681
    CA $1,662
    per traveller
    found 2 days ago
    Hotel Riu Plaza New York Times Square
  • Front of property
    Sept 2 - Sept 5

    San Carlos Hotel + Flight

    Manhattan
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,828 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,642
    CA $1,032
    per traveller
    found 2 days ago
    San Carlos Hotel
  • Breakfast served
    Sept 23 - Sept 26

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    3 nights
    4.0 star property
    9.2/10 - Wonderful (3,792 reviews)
    "Location is excellent for theater and restaurants. The breakfast was excellent with a variety for everyone but there is a charge $25. The room was clean and well appointed but the fire alarms with continuous announcements went on from 12 AM to after 1 AM. The staff are friendly and helpful."
    Reviewed July 24, 2026
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - LGA • 1 stop LGA - YHM • 1 stop
    CA $2,694
    CA $1,717
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square

Where to stay in Poughkeepsie

Find the best Poughkeepsie areas and neighborhoods for the activities you enjoy most. Learn more about Poughkeepsie
Learn more about Poughkeepsie
A lit bridge with a cross on top and a church with a steeple in the foreground.
Photo by Gregg Tobias
Open Photo by Gregg Tobias

Downtown Poughkeepsie

Downtown Poughkeepsie blends historic charm with civic energy at the heart of this Hudson Valley city. The majestic Bardavon 1869 Opera House anchors the district with its ornate Victorian façade. Stroll past well-preserved 19th-century buildings housing government offices and cultural institutions. This walkable area offers a glimpse into the city's architectural heritage. The Mid-Hudson Heritage Centre showcases local arts and diverse community culture. Visitors can explore the Mid-Hudson Civic Centre or catch performances at the historic Chance Theatre. After sightseeing, the nearby Hudson River waterfront provides a peaceful retreat. Most attractions sit within a few blocks of each other, making exploration easy and enjoyable.
A suspension bridge over a river with a forested hillside in the background.

Poughkeepsie Waterfront

You'll enjoy the restaurants and riverfront in Poughkeepsie Waterfront. You might want to make time for a stop at Mid-Hudson Bridge or Walkway Over the Hudson State Historic Park.

Arlington

Arlington blends collegiate charm with suburban tranquility just outside Poughkeepsie. Tree-lined streets wind past family homes and small commercial areas along Route 9. College life from nearby Vassar and Marist adds youthful energy to this peaceful community. The Overlook Drive-In Theatre offers nostalgic entertainment under starry skies. Art enthusiasts will appreciate the Frances Lehman Loeb Art Center's impressive collection. Budget-friendly dining options and affordable accommodations make Arlington an ideal base for exploring the Hudson Valley.
A large suspension bridge spanning a river, surrounded by dense greenery.

Crown Heights

Crown Heights offers a peaceful retreat from Poughkeepsie's busier areas with tree-lined streets and well-maintained homes. This welcoming area gives travellers an authentic slice of local suburban living. The college atmosphere adds character to this family-oriented community. Travellers appreciate the budget-friendly accommodations compared to downtown options. You'll find casual coffeehouses and family-run restaurants scattered throughout the area. The Hudson River is just a short drive away for those seeking natural beauty during their stay.
A suspension bridge over a river, surrounded by autumn foliage and urban buildings.

Red Oaks Mill

Red Oaks Mill offers a peaceful suburban retreat in the Hudson Valley region. This quiet hamlet features tree-lined streets where you can enjoy morning walks away from city noise. The residential atmosphere provides a genuine glimpse into local life. Travellers appreciate this budget-friendly alternative to downtown Poughkeepsie accommodations. A short drive connects you to riverfront areas, local breweries, and attractions like Casperkill Golf Club. Most visitors find having a car essential for exploring the beautiful surrounding countryside.

Discover the most popular places to visit in Poughkeepsie

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.

What to do in Poughkeepsie

Hallows and Hauntings of Hyde Park Ghost Tour

Hallows and Hauntings of Hyde Park Ghost Tour

CA $34
per adult
0% of travellers recommend
Hallows and Hauntings of Hyde Park Ghost Tour
See all activities in Poughkeepsie

Poughkeepsie Hotel Deals

Exterior

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG
2.5 star property
2.9 km from Poughkeepsie
8.8 out of 10, Excellent, (1,003 reviews)
"Okay stay at an okay price. Breakfast is very good. But room & bathroom not very clean."
The price is CA $105
CA $122 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express Poughkeepsie by IHG
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.
See all properties in Poughkeepsie

Frequently Asked Questions

How much does a Poughkeepsie vacation package cost?

Offering great value package deals from CA $942 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.