Pleasant Valley Vacations from $293

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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 $367, price is now $293 per person
$293
per person
Nov 21 - Nov 24
found 10 hours ago
Roundtrip flight included
San Juan (SJU) 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

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Save 100% on your flight
Price was $594, price is now $438 per person
$438
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
8.2/10 Very Good! (676 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.

Reviewed on Aug 15, 2025

Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

2 out of 5
Price was $525, price is now $433 per person
$433
per person
Oct 2 - Oct 5
found 22 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Newburgh (SWF)
7/10 Good! (1,000 reviews)
Staff was very welcoming. I found the cleanliness of the bathroom in the room could have been better.

Reviewed on Aug 26, 2025

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $417, price is now $347 per person
$347
per person
Nov 21 - Nov 24
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Newburgh (SWF)
5.8/10 (1,003 reviews)
The first floor smelled weed / cigarette and moldy as did both rooms. Bathtub was clogged in 1 room. Housepeeking did not empty garbage in bathroom or changed soap in the other room. Both rooms smelled moldy. Told the front desk at check out and she just respond with “ok”. Young lady at the check-in was probably the best part of the the stay.

Reviewed on Aug 25, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was $375, price is now $317 per person
$317
per person
Oct 2 - Oct 5
found 22 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Newburgh (SWF)
6.4/10 (1,001 reviews)
Dusty, carpet needs to be washed no elevator for a handicapped mom.I like fast check out.

Reviewed on Aug 24, 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

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

The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay

2 out of 5
192 Mcdonnell Rd, Pleasant Valley, NY
9.6/10 Exceptional! (8 reviews)
"Basic but a great stay."

Reviewed on May 22, 2025

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 2 to Sep 3
$109 total
Sep 2 - Sep 3
Total with taxes and fees
7.2/10 Good! (523 reviews)
"Our stay was good properly, was formerly or another property. It was a sheraton before, and I guess this new hotel took over for what it was worth. The hotel was nice clean comfortable. We need some upkeeping. For some remodeling, but the service was great.Bid was comfortable had no problem"

Reviewed on Aug 26, 2025

The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,050 nightly
The price is $1,176 total per night from Sep 22 to Sep 23
$1,176 total
Sep 22 - Sep 23
Total with taxes and fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
See all 1,117 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.

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Frequently asked questions

How much does a Pleasant Valley vacation package cost?
Offering excellent value package deals from $293 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.