Pleasant Valley Vacations from $414

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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 Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Great front desk presentation by the team.

Reviewed on Jul 7, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Newburgh (SWF)
9.4/10 Exceptional! (742 reviews)
I loved this hotel!!! The staff, the hotel itself, the location, everything. We will for sure stay here again

Reviewed on Jul 11, 2025

The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn

2 out of 5
Save 100% on your flight
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Newburgh (SWF)
No reviews
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Newburgh (SWF)
8.2/10 Very Good! (654 reviews)
This is my 3rd hotel in my NY trip so was the best one .

Reviewed on Jul 2, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
It was quiet but smell of cigarettes even though it’s supposed to be non smoking. The carpets were filthy. Will not stay here again

Reviewed on Jul 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

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

$65
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley

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
$131 nightly
The price is $147 total per night from Jul 20 to Jul 21
$147 total
Jul 20 - Jul 21
Total includes taxes and fees
7.8/10 Good! (1,007 reviews)
"I liked the skylight above the swimming pool. However, the pool is not heated. It felt cold going in the pool. Only one of the exercise bikes and thread mills worked. Also, the equipment is very limited. Not a lot of weights and exercise machines. The continental breakfast is great."

Reviewed on Jul 7, 2025

Best Western Plus Kingston Hotel And Conference Center
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $182 total per night from Aug 3 to Aug 4
$182 total
Aug 3 - Aug 4
Total includes taxes and fees
9.6/10 Exceptional! (354 reviews)
"Great"

Reviewed on Jul 7, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $143 total per night from Jul 27 to Jul 28
$143 total
Jul 27 - Jul 28
Total includes taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Excellent...would stay again"

Reviewed on Jul 10, 2025

HYATT house Fishkill/Poughkeepsie
See all 1,127 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 $414 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.