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Poughkeepsie Holidays

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Top Poughkeepsie flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • Meeting facility
    9 Oct - 12 Oct

    Radio Hotel + Flight

    Manhattan
    3 nights
    4.0 star property
    8.6/10 - Excellent (2,482 reviews)
    "My comforter was stained and so was the window shade. The shower faucet was broken. An item was stolen from my room and when I reported it to the manager, he told me it was “Not his problem”"
    Reviewed July 17, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • 1 stop JFK - DUB • 1 stop
    €1,127
    €726
    per traveller
    found 1 day ago
    Radio Hotel
  • Front of property
    1 Sept - 6 Sept

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.0/10 - Wonderful (3,213 reviews)
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    Save 100% on your flight
    €2,204
    €1,346
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square
  • Breakfast served
    1 Sept - 6 Sept

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (3,752 reviews)
    "Hate the facility fees"
    Reviewed July 17, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    Save 100% on your flight
    €2,074
    €1,284
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • Lobby
    1 Sept - 6 Sept

    Hotel 32 32 + Flight

    Manhattan
    5 nights
    4.0 star property
    8.0/10 - Very good (2,491 reviews)
    "Great staff, very helpful. Outstanding location. Clean. reading lights were not working, shower door had a broken part sitting in the shower area."
    Reviewed July 17, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct JFK - DUB • Direct
    Save 100% on your flight
    €1,535
    €977
    per traveller
    found 1 day ago
    Hotel 32 32
  • Exterior
    20 Sept - 26 Sept

    Roxy Hotel New York + Flight

    Manhattan
    6 nights
    4.5 star property
    9.4/10 - Exceptional (1,600 reviews)
    "Beautiful hotel, incredible staff and service. Entertainment at Roxy was fabulous!"
    Reviewed July 16, 2026
    Return • Dublin (DUB) - New York (JFK)
    DUB - JFK • Direct EWR - DUB • Direct
    Save 100% on your flight
    €3,062
    €1,971
    per traveller
    found 1 day ago
    Roxy Hotel New York

Where to stay in Poughkeepsie

Find the best Poughkeepsie areas for the activities you enjoy most.
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

City centre 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 accommodation 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 accommodation compared to city centre 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 city centre Poughkeepsie accommodation. 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)
Explore the only National Historic Site dedicated to a First Lady at Eleanor Roosevelt's Val-Kill Cottage. Wander through her modest home where she shaped her humanitarian legacy after FDR's presidency.

What to do in Poughkeepsie

Hallows and Hauntings of Hyde Park Ghost Tour

Hallows and Hauntings of Hyde Park Ghost Tour

€21
per adult
0% of travellers recommend
Hallows and Hauntings of Hyde Park Ghost Tour
See all activities in Poughkeepsie

Poughkeepsie Hotel Deals

Restaurant

Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz
2.0 star property
12.3 km from Poughkeepsie
9.0 out of 10, Wonderful, (1,001 reviews)
"This is a fine room for a good price. Nothing fancy but it serves its outhouse."
The price is €114
includes taxes & fees
5 Aug - 6 Aug
Americas Best Value Inn New Paltz
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 holiday package cost?

You'll find cheap prices from €726 on Expedia for your Poughkeepsie escape. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Poughkeepsie costs.

What are the cheapest months to go to Poughkeepsie?

You can generally find reduced prices and better availability in January, February and March. Check out our cheap Poughkeepsie holiday packages and you could get some excellent off-season deals.

How many days is enough for Poughkeepsie?

Poughkeepsie holidays come in many shapes and sizes, but to get a real feel for this place, we'd suggest 2 days is about right. In this timeframe, you can visit top attractions like Mid-Hudson Children's Museum and Bardavon 1869 Opera House as well as underrated spots. Don't skip cool areas such as Crown Heights and Spackenkill either. If you're clever with your time, you can even take a day trip or two from Poughkeepsie too.

Is it worth booking a holiday package to Poughkeepsie?

Poughkeepsie offers everything you need for an unforgettable escape. Get your Poughkeepsie holiday off to a flying start by visiting popular attractions like Poughkeepsie Bridge.

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 customise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?

Expedia holiday 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 personalised Poughkeepsie holiday by choosing your favourite accommodation type, airline and car class.

When to book a holiday 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. Choose when to travel: Check your diary and get your bags packed. Your favourite season and the type of activities available will also help you decide when to visit Poughkeepsie.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to experiences and flights. Your hotel will probably be the biggest expense during your trip to Poughkeepsie.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Poughkeepsie. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodation: Once you've settled on your trip dates and duration, lock in the ideal Poughkeepsie holiday package for you.

Book with confidence

Things to do in and around Poughkeepsie

Poughkeepsie offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal day getaway. Visitors can enjoy educational and culinary tours, explore charming shopping areas, and partake in house tours. With its recreational spaces and vibrant shopping experiences, Poughkeepsie promises a memorable visit filled with diverse attractions and unique ticketed events.

Shopping

Poughkeepsie offers a delightful shopping experience. The Poughkeepsie Galleria, located 9.7km away, features a variety of shops and entertainment options. If you're up for a drive, visit the Stormville Airport Antique Show & Flea Market, 20.9km away, or the Hudson Valley Mall, 29.0km away for more family-friendly vibes.

Recreation

The Overlook Drive-In Theater offers a nostalgic cinema experience under the stars, perfect for a romantic evening. The Apple Greens Golf Course invites golfers to enjoy the outdoors amidst scenic views, while Bananas Comedy Club promises a fun-filled night of laughter for the whole family.

Adventure

SplashDown Beach, located 17.7km from Poughkeepsie, offers thrilling water slides and family fun in a vibrant atmosphere. For arcade enthusiasts, Fun Central, 11.3km away, features exciting games and activities. Paintball Sports, found 12.9km from the city, provides an adrenaline-filled adventure for competitive spirits.

Nightlife

Poughkeepsie's nightlife is vibrant, featuring numerous bars and venues. Visit The Bardavon for live performances, or enjoy a cocktail at The Piano Lounge. For a relaxed evening, head to The Coyote Flaco for tasty Mexican fare and margaritas while soaking in the lively atmosphere.

Find the best attractions in and around Poughkeepsie

Poughkeepsie, New York, is an excellent destination for outdoor and family adventures, featuring a blend of modern colleges, historic sites, and the iconic Poughkeepsie Bridge. Visitors can explore the Poughkeepsie Galleria and various local attractions that cater to those seeking cultural and outdoor experiences. Whether you're planning a trip to Poughkeepsie or looking for activities to enjoy, this charming city offers a delightful escape for all types of travellers.

  • Vassar College: Experience the vibrant atmosphere of this prestigious liberal arts college, known for its stunning architecture and beautiful campus grounds. Explore the blend of modernity and tradition, with art installations and cultural events often taking place.
  • Mid-Hudson Bridge: Walk across this historic bridge for breathtaking views of the Hudson River. It serves as a vital link between Poughkeepsie and Highland, showcasing the region's rich history and offering a unique perspective on the local culture.
  • Chadwick Lake Park: Discover this family-friendly urban park, perfect for outdoor activities such as hiking, picnicking, and fishing. With its serene lake and walking trails, it's an ideal spot for relaxation and enjoying nature just outside the city.

Best time to go to Poughkeepsie

The best time to visit Poughkeepsie can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Poughkeepsie falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Poughkeepsie falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Tips to save on your trip to Poughkeepsie

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.