Pleasant Valley Vacations from $233

Book a Hotel + Flight or Car together to unlock savings

Photo by louann ohora

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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $280, price is now $233 per person
$233
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.4/10 Good! (534 reviews)
Elevator out of order...shoddy bathroom repair, no hot water in sink, no light over sink, top of door catches on ceiling light fixture. Beds were clean and comfortable...TV hard to figure out if you're not an AV Technician. One ice machine on the third floor walkup.

Reviewed on Sep 5, 2025

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Price was $819, price is now $613 per person
$613
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newburgh (SWF)
8/10 Very Good! (1,699 reviews)
The dining options were not great and the food wasn’t that good.

Reviewed on Sep 4, 2025

The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay

2 out of 5
Save 100% on your flight
Price was $587, price is now $462 per person
$462
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
9.6/10 Exceptional! (8 reviews)
Basic but a great stay.

Reviewed on May 22, 2025

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 $326, price is now $272 per person
$272
per person
Oct 8 - Oct 11
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
5.4/10 (1,010 reviews)
There was only oat meal for the light breakfast. The washer was out of order and the dryer didn’t dry the clothes. Friendly staff at the front desk. The other employees don’t speak English and will talk into your phone to have it translated.

Reviewed on Aug 18, 2025

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Price was $925, price is now $778 per person
$778
per person
Nov 26 - Dec 1
found 23 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8.4/10 Very Good! (1,010 reviews)
Wonderful place to stay. The breakfast was delicious, the only thing probably the small pool too much chlorine and too close, and they don't have enough towels

Reviewed on Aug 31, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pleasant Valley
View all trips

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
See all activities in Pleasant Valley

Pleasant Valley Hotel Deals

The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay

2 out of 5
192 Mcdonnell Rd, Pleasant Valley, NY
Get rates
The Lagrange Inn & Extended Stay
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$93 nightly
The price is $109 total per night from Sep 11 to Sep 12
$109 total
Sep 11 - Sep 12
Total with taxes and fees
The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,059 nightly
The price is $1,187 total per night from Sep 22 to Sep 23
$1,187 total
Sep 22 - Sep 23
Total with taxes and fees
Wildflower Farms, Auberge Resorts Collection
See all 1,114 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pleasant Valley vacation package cost?
Offering excellent value package deals from $233 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

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.