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

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

2 out of 5
per person
Jun. 30 - Jul. 4
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
Loved the view from the rooms.

Reviewed on Apr. 22, 2025

La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Newburgh (SWF)
9.4/10 Exceptional! (648 reviews)
The receptionist is an absolute pro: friendly and eager to help improve our stay. She should be running the NYC Four Seasons... Anyway, location is great with Starbucks across the lot. Hotel is quiet and extremely clean. It looks brand new both inside and out. We'll keep coming again and again.

Reviewed on Apr. 29, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
7.8/10 Good! (378 reviews)
Front doors is unsafe I went outside and came back to my room door was half way open secured door lock was hard to close I had to pull up an the door to close it’s what it is cheap for a get away.

Reviewed on Apr. 26, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
8.2/10 Very Good! (619 reviews)
Everything went well

Reviewed on Apr. 20, 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Jun. 14 - Jun. 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (986 reviews)
Clean and comfortable. Staff very friendly.

Reviewed on Apr. 30, 2025

Ready to book your vacation to Pleasant Valley?

 

Choose your dates

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
The price is CA $157 per night from May 6 to May 7
CA $157
CA $176 total
includes taxes & fees
May 6 - May 7
7.8/10 Good! (1,001 reviews)
"Very quiet. A bit outdated and in need of some basic repairs. Otherwise, no complaints."

Reviewed on Apr. 29, 2025

Best Western Plus Kingston Hotel And Conference Center
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
The price is CA $152 per night from May 11 to May 12
CA $152
CA $172 total
includes taxes & fees
May 11 - May 12
8.6/10 Excellent! (1,012 reviews)
"Super clean"

Reviewed on Apr. 28, 2025

HYATT house Fishkill/Poughkeepsie
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 $223 per night from May 18 to May 19
CA $223
CA $252 total
includes taxes & fees
May 18 - May 19
9.6/10 Exceptional! (315 reviews)
"Only a year old. Nice room. Great Staff."

Reviewed on Apr. 28, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,097 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 $706 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
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.