Pleasant Valley Vacations
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Your Pleasant Valley Vacation
The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like Marist College, Vassar College and Culinary Institute of America. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia.
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.
What to do in Pleasant Valley
Hallows and Hauntings of Hyde Park Ghost Tour
$24
per adult
Pleasant Valley Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
$152 nightly
$172 total
Sep 10 - Sep 11
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
$97 nightly
$113 total
Sep 13 - Sep 14
Total with taxes and fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$97 nightly
$113 total
Sep 20 - Sep 21
Total with taxes and fees
9/10 Wonderful! (1,068 reviews)
"Comfortable room, got extra pillows that we requested. Very good breakfast choices, good coffee. We're actually coming back in 2 weeks for my husband's 2nd eye surgery!"
Reviewed on Sep 8, 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.
Find the Best Pleasant Valley Vacation Packages
Pleasant Valley Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 1,150 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Millbrook Vineyards and Winery, Wings Castle and Chance Theater |
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Frequently asked questions
How much does a Pleasant Valley vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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?
If you'd like to score a cheap Pleasant Valley vacation package, consider visiting in December, January and February. You'll typically find lower prices on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Pleasant Valley?
Typically, a handful of days is enough to see the major sights during your Pleasant Valley vacation. But if you want to have time to rest or go on day trips, think about extending your trip.
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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Pleasant Valley vacation as a package?
Expedia vacation 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 personalized Pleasant Valley vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 your travel dates: What you want to do in Pleasant Valley and your favorite season will help you decide when to go.
- Budget wisely: On top of the price of your accommodations, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Pleasant Valley.
- Organize your Pleasant Valley escape with Expedia's trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Pleasant Valley together.
- Work out your trip length: Consider how much time you'd like to spend exploring Pleasant Valley. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Pleasant Valley vacation package that brings all your bookings together.
- Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the best Pleasant Valley has to offer. Find all the fun things to do in Pleasant Valley with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Pleasant Valley vacation packages?
Secure your perfect escape to Pleasant Valley with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until the next payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals before they disappear.
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- Iona College
- Culinary Institute of America
- Springside National Historic Site
- Marist College
- Visit Poughkeepsie
- Philipse Manor Hall State Historic Site
- Bananas Comedy Club
- Mid-Hudson Bridge
- Newyork-Presbyterian - Westchester Hospital
- Sprain Lake Golf Course
- Overlook Drive-In Theater
- College of New Rochelle
- Vanderbilt Mansion National Historic Site
- Westchester Hills Cemetery
- Vassar College
- Vassar Brothers Medical Center
- Cudner-Hyatt House Complex
- Mount Vernon Vacations
- Thomas Paine Cottage Museum
- Monroe College New Rochelle Campus
- Sarah Lawrence College
- Yonkers Raceway
- Poughkeepsie Bridge
- Crooked Island Caves
- Empire City Casino
- Clinton Corners Vacations
- Edward J. Murray Memorial Skating Center
- College of Mount Saint Vincent
- New Rochelle Vacations
- Innisfree Garden
- Dobbs Ferry Vacations
- East Fishkill Community Library
- Yonkers Vacations
- Splashdown Beach
- Walkway Over the Hudson State Historic Park
- Hyde Park Landing
- Scarsdale Vacations
- Casperkill Golf Club
- Franklin D. Roosevelt Presidential Library and Museum
- New Roc City
- Hyde Park Vacations
- Hudson River Museum
- Orvis Sandanona Shooting Grounds
- Clinton House State Historic Site
- Home of Franklin D. Roosevelt National Historic Site
- Hastings-On-Hudson Vacations
- Wing's Castle
- Haviland Vacations
- Tibbetts Brook Park
- Lenoir Preserve
- Omega Institute
- Eleanor Roosevelt National Historic Site
- James Baird State Park
- Tuckahoe Vacations
- Hyde Park Railroad Station
- Richard L. Skimin Memorial Baseball Field
- Palisades Vacations
- Saint Vladimir's Orthodox Theological Seminary
- Visit Rhinebeck
- Poughkeepsie Vacations
- Science Barge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
