Pleasant Valley Vacations from $169

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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.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
Price was $238, price is now $169 per person
$169
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
The stay was excellent. The pool was a perfect temp for all to unwind after a long drive. We enjoyed the breakfast. The staff was very friendly and helpful.

Reviewed on Dec 2, 2025

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
Price was $415, price is now $322 per person
$322
per person
Jan 16 - Jan 21
found 2 hours ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.6/10 Excellent! (1,000 reviews)
Very kind and friendly front desk staff. Room clean, Fast check in.

Reviewed on Dec 2, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $340, price is now $274 per person
$274
per person
Feb 13 - Feb 16
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.2/10 Very Good! (691 reviews)
Great location and it felt pretty safe overall. The only downside was that the room didn’t have proper humidity ventilation, and the hallway AC made it cold, so we had to use the heater to balance the temperature. Other than that, the staff was super friendly, and the property was very well maintained.

Reviewed on Oct 30, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $241, price is now $194 per person
$194
per person
Jan 5 - Jan 9
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
6/10 (1,002 reviews)
clean room great staff

Reviewed on Nov 28, 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was $355, price is now $295 per person
$295
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
9.2/10 Wonderful! (967 reviews)
Room was comfortable and spacious

Reviewed on Nov 27, 2025

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Discover the most popular places to visit in Pleasant Valley

Just a sneak peak at a most wonderful gem of a 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

What to do in Pleasant Valley

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

$48
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

$67
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley

Pleasant Valley Hotel Deals

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
$99 nightly
The price is $115 total per night from Dec 12 to Dec 13
$115 total
Dec 12 - Dec 13
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Comfortable room

Reviewed on Nov 30, 2025

Hampton Inn & Suites Poughkeepsie
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Jan 1 to Jan 2
$114 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (1,016 reviews)
Good hotel. No frills

Reviewed on Nov 29, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
$111 nightly
The price is $124 total per night from Jan 1 to Jan 2
$124 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (781 reviews)
Friendly staff, it is always clean, welcoming entrance , close by shopping , best breakfast coffee. We like the water and cookies in the afternoon . Hotel room clean. Our room was not ready and Manager gave us a discounted rate on our pet fee.

Reviewed on Nov 23, 2025

Residence Inn by Marriott Kingston
See all 1,120 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 $169 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.

Explore a world of travel with Expedia

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