Pleasant Valley Holidays

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Your Pleasant Valley Holiday

Reserve a Pleasant Valley holiday package that has only the things you need and nothing you don't. Good for history, families and culture, consider staying in the neighbourhood of Poughkeepsie Waterfront. Like to explore? Marist College, Culinary Institute of America and Vassar College are just three of the top-rated places to visit during your trip to Pleasant Valley. Whatever your travel plans or the size of your budget, organising a tailored Pleasant Valley holiday is easy with Expedia.

Pleasant Valley Holiday

Pleasant Valley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
1,150
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Millbrook Vineyards and Winery, Chance Theatre and Wings Castle

Our pick of the best Pleasant Valley Hotel Deals

Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 12 Aug to 13 Aug
AU$148
12 Aug - 13 Aug
includes taxes & fees
8.4/10 Very good! (180 reviews)
"The room was clean; small refrigerator; bathroom vanity not in the bathroom; ice only available on the ground floor."

Reviewed on 21 July 2026

Spark by Hilton Fishkill
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
The price is AU$183 per night from 4 Aug to 5 Aug
AU$183
4 Aug - 5 Aug
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
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 AU$196 per night from 4 Aug to 5 Aug
AU$196
4 Aug - 5 Aug
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
"The hotel and check in staff were wonderful. My room was clean and included water and tea/coffee. Disappointing that we were not offered warm cookies at check in or check out and had to ask for them! Housekeeping was short staffed and our room wasn't cleaned until late in the day. This made it difficult ..."

Reviewed on 21 July 2026

DoubleTree by Hilton Poughkeepsie Convention Center
See all 1,129 properties in Pleasant Valley
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Pleasant Valley attractions

Innisfree Garden

10.0/10 (2 reviews)
This 185-acre masterpiece blends Modernist design with Chinese and Japanese garden traditions around a stunning 40-acre lake. Explore waterfalls, streams, and rocky outcrops along the peaceful 1.3-mile lakeside path.
See properties

What to do in Pleasant Valley

Hallows and Hauntings of Hyde Park Ghost Tour

Hallows and Hauntings of Hyde Park Ghost Tour

AU$35
per adult
Hallows and Hauntings of Hyde Park Ghost Tour
See all activities in Pleasant Valley

Frequently asked questions

How much does a Pleasant Valley holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Pleasant Valley costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pleasant Valley?
Plan your trip for the off-peak season and you're likely to find cheap Pleasant Valley holiday packages. Keep in mind that school holiday periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Pleasant Valley?
For your Pleasant Valley holiday, a few days will be enough to tour all the highlights. Make sure to stop by Innisfree Garden — it's one of the most popular sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some trips from Pleasant Valley.
How to find the best Pleasant Valley package deals?
Finding a cheap Pleasant Valley package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Pleasant Valley package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Pleasant Valley holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still get the flexibility to create a personalised Pleasant Valley holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Pleasant Valley?
If you're planning an impromptu Pleasant Valley adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Pleasant Valley?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Pleasant Valley.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your hotel will likely be the biggest expense during your trip to Pleasant Valley.
  3. Decide how long to go for: Now that you're up to speed on Pleasant Valley, you can work out the perfect length of your holiday. Create a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Pleasant Valley holiday package that brings all your bookings together.

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