Pleasant Valley Vacation Packages

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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.

Top Pleasant Valley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was CA $905, price is now CA $745 per person
CA $745
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
8.6/10 Excellent! (1,011 reviews)
Very clean , beautiful room

Reviewed on Aug. 24, 2025

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Price was CA $1,035, price is now CA $754 per person
CA $754
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
8/10 Very Good! (1,657 reviews)
Staff and mananger was really friendy. Property was nice clean.

Reviewed on Aug. 23, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
Price was CA $1,285, price is now CA $1,004 per person
CA $1,004
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Love the yoga love the room very clean pool and hot tub were amazing. Just wish they were open longer. Did not love the food.

Reviewed on Aug. 23, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was CA $1,692, price is now CA $1,365 per person
CA $1,365
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Québec (YQB) 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

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 CA $1,274, price is now CA $1,108 per person
CA $1,108
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Québec (YQB) 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

Ready to book your vacation to Pleasant Valley?

 

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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
The price is CA $136 per night from Sep 2 to Sep 3
CA $136
CA $160 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug. 21, 2025

The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,392 per night from Sep 24 to Sep 25
CA $1,392
CA $1,619 total
Sep 24 - Sep 25
includes taxes & 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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What to do in Pleasant Valley

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

CA $66
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

CA $92
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley

Frequently asked questions

How much does a Pleasant Valley vacation package cost?
You'll find cheap prices from CA $745 on Expedia for your Pleasant Valley escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Pleasant Valley costs.
What are the cheapest months to go to Pleasant Valley?
To pick up cheap Pleasant Valley vacation packages, plan your getaway outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Pleasant Valley?
We'd suggest booking a Pleasant Valley vacation for at least 3 days. This gives you enough time to check off popular sights including James Baird State Park and Vassar Golf Course, and check out neighbourhoods like Arlington and Fairview. You might even be able to slot in a day trip or two from Pleasant Valley.
How to find the best Pleasant Valley package deals?
Landing a cheap Pleasant Valley package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Pleasant Valley package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually 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 hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Pleasant Valley vacation by choosing your favourite type of stay, airline and car class.
How to plan a trip to Pleasant Valley?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Pleasant Valley.
  2. Set your budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Pleasant Valley. Then, choose a hotel that works with your budget, whether that's a low-cost option or a swankier retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Pleasant Valley. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, lock in the right Pleasant Valley vacation package for you.

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