Pleasant Valley Vacations from $408

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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.

The Latest Pleasant Valley vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $463, price is now $408 per person
$408
per person
Jun 10 - Jun 14
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Newburgh (SWF)
5.4/10 (1,003 reviews)
Staffs were extremely kind.

Reviewed on Jan 4, 2026

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $849, price is now $653 per person
$653
per person
Jun 4 - Jun 8
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
Older room with chemical cleaning solution smell

Reviewed on Mar 24, 2026

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $600, price is now $494 per person
$494
per person
Jun 10 - Jun 14
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Newburgh (SWF)
8.6/10 Excellent! (1,015 reviews)
Clean room, safe and staff is courteous

Reviewed on Mar 19, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $728, price is now $640 per person
$640
per person
Jun 10 - Jun 14
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel

Reviewed on Feb 27, 2026

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $514, price is now $459 per person
$459
per person
Jun 10 - Jun 14
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Newburgh (SWF)
7/10 Good! (729 reviews)
Not too bad a place if you just need to crash & leave early. Comfy beds, a bit outdated though. Even though the rooms were non smoking you could still smell a bit from when you could smoke there in the room & throughout the building. Very spotty WiFi, so if you need to internet to work at all, not ideal.

Reviewed on Mar 7, 2026

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Discover the most popular places to visit in Pleasant Valley

Innisfree Garden

Innisfree Garden

5/5(1 review)

Explore the great outdoors at Innisfree Garden, a lovely green space in Pleasant Valley. Wander the riverfront in this family-friendly area.

Innisfree Garden

James Baird State Park

You can take time to visit James Baird State Park during your travels to Pleasant Valley. Attend a sporting event or visit the shops in this family-friendly area.

James Baird State Park

Pleasant Valley Hotel Deals

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $116 total per night from Apr 2 to Apr 3
$116 total
Apr 2 - Apr 3
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
There was a mystery pill found on the floor in the room. Lucky my dog didnt eat it. Still taking him to the vet. The hotel staff had nothing to say about it and even tried to take away the evidence. Also, anyone can walk in and wander around. Doors open without a key.

Reviewed on Mar 23, 2026

Best Western Plus Kingston Hotel And Conference 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
$116 nightly
The price is $134 total per night from Apr 2 to Apr 3
$134 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Clean room with comfortable bed and nice bathroom. Friendly staff.

Reviewed on Mar 23, 2026

Hampton Inn & Suites Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
$1,093 nightly
The price is $1,224 total per night from Apr 1 to Apr 2
$1,224 total
Apr 1 - Apr 2
Total with taxes and fees
Wildflower Farms, Auberge Collection
See all 1,098 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.

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 from $408 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?

  1. Pick your travel dates: What you want to do in Pleasant Valley and your favorite season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.