Poughkeepsie Holidays

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Top Flight + Hotel Deals in Poughkeepsie

Price found within the past 48 hours. Click for updated prices.
Hilltop Inn & Suites

Hilltop Inn & Suites

2.5 out of 5
Northwest Yonkers
per person
24 Sept - 28 Sept
found 1 day ago
Return flight included
Dublin (DUB) to White Plains (HPN)
6.8/10 (316 reviews)
Convenience store and dominos were close enough to walk and get food/snacks. The room smelled like dust and tobacco. The door needed to be slammed in order to close correctly. Walls were thin enough to hear conversations from next door. Cleaning staff came in while I was away and threw away part of a toy I bought for my little brother. Key card stopped working when I got back late at night so I had to ask for it to be fixed. Beds were clean and nicely made. Outlets worked well, TV was small but nice and wifi worked well.

Reviewed on 9 Aug 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to White Plains (HPN)
2/10 (1 review)
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
Northwest Yonkers
per person
24 Sept - 28 Sept
found 1 day ago
Return flight included
Dublin (DUB) to White Plains (HPN)
8.2/10 Very Good! (2,197 reviews)
I love this place and the staff ! Excellent place to stay !! It’s very clean and the area is quiet and nice ! The staff are awesome .

Reviewed on 6 Aug 2025

Stamford Suites

Stamford Suites

4 out of 5
Downtown Stamford
per person
10 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to White Plains (HPN)
5.6/10 (48 reviews)
While the physical property is well maintained, generally it could use a facelift and update. Also, the windows have not been cleaned in some Time!

Reviewed on 13 Jul 2025

The Opus Westchester, Autograph Collection

The Opus Westchester, Autograph Collection

5 out of 5
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to White Plains (HPN)
9.2/10 Wonderful! (504 reviews)
Although I stayed for 1 night, I wish my stay was a little longer. This hotel exceeds my expectations. I had a wonderful time and stay. The spa was so beautiful and amazing. I would definitely recommend this hotel.

Reviewed on 21 Jul 2025

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 coffee shops 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

Top hotels in 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
The price is €109 per night from 24 Aug to 25 Aug
€109
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"

Reviewed on 3 Aug 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
The price is €114 per night from 18 Aug to 19 Aug
€114
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Great everything. Not the best part of town but totally fine."

Reviewed on 8 Aug 2025

DoubleTree by Hilton Poughkeepsie Convention Center
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
The price is €114 per night from 17 Aug to 18 Aug
€114
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Great hotel
"You may want to check the thermometer in 529. It was set on 68 but was more like 78 in the room. Other than that, we had a great stay!"

Reviewed on 8 Aug 2025

Hampton Inn & Suites Poughkeepsie
See all 2,487 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.

Popular places to visit

Mid-Hudson Bridge showing a bridge, a bay or harbour 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

Vassar College

Enjoy the student vibe when you visit Vassar College during your travels in Poughkeepsie. Amble around the area's riverfront or attend a sporting event.

Vassar College

Marist College

Enjoy the student vibe when you visit Marist College during your travels in Poughkeepsie. While you're in the area, stroll along the riverfront.

Marist College

What to do in Poughkeepsie

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

€41
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

€58
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

€137
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
See all activities in Poughkeepsie

Frequently asked questions

How much does a Poughkeepsie holiday package cost?
You'll find cheap prices from €551 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.