Pleasant Valley Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pleasant Valley

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 2.891.020 ₫ per night from 3 Sept to 4 Sept
2.891.020 ₫
3.357.196 ₫ total
3 Sept - 4 Sept
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
The price is 3.969.896 ₫ per night from 10 Aug to 11 Aug
3.969.896 ₫
4.490.945 ₫ total
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very good! (953 reviews)
"The room was clean and well furnished and the front desk staff were friendly and very helpful. Even though we were technically in a room where dogs were allowed, the room did not smell like dogs and there was not a trace that anyone had slept in it that had a dog, which is a plus. Love dogs, but ..."

Reviewed on 4 Aug 2026

Beekman Arms and Delamater Inn
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is 2.389.034 ₫ per night from 31 Aug to 1 Sept
2.389.034 ₫
2.774.266 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"The young lady working the front desk was unwelcoming and cold. We reserved this hotel particularly for the outdoor pool which probably hasn’t been open for months/year. Very deceiving"

Reviewed on 3 Aug 2026

Holiday Inn Express Poughkeepsie by IHG
See all 1,128 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.

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.
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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.