Pleasant Valley Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by louann ohora
    deals illustration
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Aug 16 - Aug 19
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
5.8/10 (1,001 reviews)
It was good for overnight stay.

Reviewed on Jun. 19, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Sep 4 - Sep 8
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (646 reviews)
Loved facility...nice customer service.

Reviewed on Jun. 24, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
7.6/10 Good! (438 reviews)
The beds were comfortable but the property was not the cleanest and when we walked out of our room we were hit with the strongest smell of pot every time.

Reviewed on Jun. 28, 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
per person
Aug 1 - Aug 4
just found
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
5.4/10 (1,005 reviews)
When i checked in they gave me a room key walked up the second floor opened door and the room was trashed and looks like people already had the room walked back down to front desk the person behind the desk apologized and gave me a new room other then that the stay was nice the new room was clean

Reviewed on Jun. 23, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Sep 10 - Sep 13
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
8.4/10 Very Good! (1,007 reviews)
The cleaning people was nice , The bed was uncomfortable. The pool was nasty with bugs, didn't know the stop severing breakfast, it was ok but i wouldn't go back there not for the price not worth it..

Reviewed on Jun. 26, 2025

Ready to book your vacation to Pleasant Valley?

 

Choose your dates

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
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
The price is CA $179 per night from Jul 6 to Jul 7
CA $179
CA $201 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Great spot in Kingston, perfect for venturing into the Historic district, or driving over to Woodstock or the Catskills. Check-in took a while due to short staffing."

Reviewed on Jun. 21, 2025

Best Western Plus Kingston Hotel And Conference Center
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
The price is CA $151 per night from Jul 10 to Jul 11
CA $151
CA $175 total
Jul 10 - Jul 11
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"It was very nice, but jacuzzi was closed."

Reviewed on Jun. 26, 2025

Hampton Inn & Suites Poughkeepsie
See all 1,122 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pleasant Valley vacation package cost?
You'll find cheap prices from CA $524 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.

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 $89
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.