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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
7.4/10 Good! (492 reviews)
Good value property. Room was updated and very comfortable. Staff was very friendly and helpful. Hallways and other common areas could use some refreshing. Would stay again.

Reviewed on Aug. 6, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
9.2/10 Wonderful! (770 reviews)
Place was great have stayed here many times.

Reviewed on Jul. 30, 2025

The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn

2 out of 5
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
No reviews
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,012 reviews)
Every time I stay at the Red roof Inn, I am never disappointed. It is an excellent hotel that is safe, clean, and the staff is fabulous. I highly recommend it.

Reviewed on Aug. 6, 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Oct 9 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
9.2/10 Wonderful! (924 reviews)
The Hotel its self was nice and clean. Staff was okay, not overly welcoming. The area that we were in was not the best and that was coming from a Sheriff we had met at the hotel. Area has high drugs and crime. We actually saw someone being arrested for theft at the gas station down the street. We were there just for an overnight so it was okay.

Reviewed on Aug. 6, 2025

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Pleasant Valley Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is CA $117 per night from Sep 7 to Sep 8
CA $117
CA $139 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (501 reviews)
"Beds are comfortable with great bedding"

Reviewed on Aug. 5, 2025

The Crossroads Hotel, Newburgh
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $174 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"

Reviewed on Aug. 3, 2025

Holiday Inn Express Poughkeepsie by IHG
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
The price is CA $221 per night from Sep 1 to Sep 2
CA $221
CA $250 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (371 reviews)
"Loved this modern and clean hotel."

Reviewed on Aug. 1, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,124 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 $637 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.