Pleasant Valley Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Pleasant Valley
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
€105
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,035 reviews)
"Great stay"
Reviewed on 10 Aug 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
€120
11 Aug - 12 Aug
includes taxes & fees
8.2/10 Very good! (963 reviews)
"Stayed in one of the outer buildings. Room was beautiful...very clean and spacious. Bed was comfortable. Air conditioner worked well, but was a bit noisy. Main reason for losing a star was the poor continental breakfast. Very small selection of items."
Reviewed on 10 Aug 2026
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
€78
9 Sept - 10 Sept
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Right off the main road, easy check in/check out, very clean!"
Reviewed on 10 Aug 2026
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.
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.
James Baird State Park
This Robert Trent Jones-designed golf course anchors a state park with woodland trails. Enjoy the challenging greens or explore other recreational facilities including tennis courts and picnic areas.
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?
- 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.
- 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.
- 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.
- 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.
