Pleasant Valley Vacations from $189

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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 Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
Price was $240, price is now $189 per person
$189
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
6.2/10 (1,004 reviews)
Dislike: The carpets in the hallways were dirty. There was dirty hotel laundry and smelly garbage cans in the hallway by my room. A giant water stain on the ceiling above the shower. Likes: The staff was friendly, there was a restaurant right outside the door of the hotel, the hotel was conveniently located for my trip, and the price was reasonable. I had no probably staying there but if the wife was with me we would of left right away.

Reviewed on Oct 14, 2025

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
Price was $710, price is now $455 per person
$455
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
8.2/10 Very Good! (1,754 reviews)
Adam was amazing and this place was so complete with everything you need to give kids a great experience.

Reviewed on Oct 19, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $422, price is now $345 per person
$345
per person
Nov 23 - Nov 28
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
6/10 (1,009 reviews)
Don't rely on breakfast

Reviewed on Oct 15, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $261, price is now $218 per person
$218
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
7.2/10 Good! (617 reviews)
Staff were great. Room and building is in need of repair.

Reviewed on Oct 19, 2025

Cottage Suites

Cottage Suites

2 out of 5
Price was $423, price is now $356 per person
$356
per person
Nov 25 - Nov 28
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
5/10 (8 reviews)
The owner did not reply to my outreach and provided no means of contact. It was very hard to find the building at night as it is situated in a multi-street intersection. There was also no guidance on parking. I ended up booking a different place to stay overnight.

Reviewed on Sep 1, 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

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

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

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 Oct 20 to Oct 21
$109 total
Oct 20 - Oct 21
Total with taxes and fees
7.2/10 Good! (618 reviews)
"This time got very clean and spacious room. All was great!"

Reviewed on Oct 14, 2025

The Crossroads Hotel, Newburgh
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
$110 nightly
The price is $128 total per night from Nov 2 to Nov 3
$128 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,036 reviews)
"Good"

Reviewed on Oct 18, 2025

Hampton Inn & Suites Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,144 nightly
The price is $1,281 total per night from Nov 18 to Nov 19
$1,281 total
Nov 18 - Nov 19
Total with taxes and fees
9.4/10 Exceptional! (54 reviews)
"Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ..."

Reviewed on Sep 16, 2025

Wildflower Farms, Auberge Collection
See all 1,115 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.

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 $189 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.