Pleasant Valley Vacations from $431

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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.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $559, price is now $431 per person
$431
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
Easy check in, clean and smoke free, friendly staff, nice rooms, hot breakfast; would stay again!!!!

Reviewed on Jan 20, 2026

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Save 100% on your flight
Price was $789, price is now $625 per person
$625
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.4/10 Very Good! (1,003 reviews)
January 2026 - Hotel is currently undergoing significant renovations. First floor was an absolute disaster in hallways, horrendous paint smell, etc. The site did the best they could do to not interfere with guest stays but would have chosen to stay elsewhere if it was known on the Expedia that the hotel was under renovations. Elevator was out of service due to an "incident" so had to traverse 3 stories each direction during the stay. Pool was warm, clean, and well maintained. Overall front desk experience was excellent, and breakfast selection was satisfactory.

Reviewed on Jan 12, 2026

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Price was $667, price is now $570 per person
$570
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.6/10 Excellent! (1,000 reviews)
Room was really nice and spacious and clean. Definitely nicer than most. The lobby was beautiful with fireplaces and comfortable furniture. It was just the food situation and sparse staffing that would make me never stay here again. There was no complimentary coffee in the lobby — even the cheepest most terrible places have that. And the breakfast situation sounds a lot better than it is. There were few choices and just one guy back there taking orders, cooking it and serving it. I watched a man wait ten minutes just to buy an expensive cup of black coffee while the cook made our food. No one was there to help him. This is not the staff’s fault — it’s the management/corporate decisions that make this place not a pleasant place who want to enjoy the hotel experience beyond just a nice room. I think simple things like coffee in the lobby, more staff, and more breakfast choices wouid go a long way

Reviewed on Jan 5, 2026

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
Price was $848, price is now $730 per person
$730
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.8/10 Excellent! (695 reviews)
This was a wonderful experience, hotel was amazing as well as staff. I would stay again

Reviewed on Jan 18, 2026

Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG

2.5 out of 5
Price was $661, price is now $574 per person
$574
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.8/10 Excellent! (31 reviews)
Great staff and very clean room.

Reviewed on Jan 6, 2026

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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

Pleasant Valley Hotel Deals

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Feb 8 to Feb 9
$101 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Very good n clean

Reviewed on Jan 24, 2026

Courtyard by Marriott Poughkeepsie
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $138 total per night from Mar 1 to Mar 2
$138 total
Mar 1 - Mar 2
Total with taxes and fees
8.8/10 Excellent! (833 reviews)
Have stayed here many times. they have done a really good job of keeping the property up to date. Very nice people.

Reviewed on Jan 25, 2026

Residence Inn by Marriott Kingston
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
$161 nightly
The price is $182 total per night from Feb 11 to Feb 12
$182 total
Feb 11 - Feb 12
Total with taxes and fees
9.6/10 Exceptional! (459 reviews)
Tasteful, large room, and pleasant staff.

Reviewed on Jan 25, 2026

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,113 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.

Find the Best Pleasant Valley Vacation Packages

Pleasant Valley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
1,150
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Millbrook Vineyards and Winery, Wings Castle and Chance Theater

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Frequently asked questions

How much does a Pleasant Valley vacation package cost?
Offering excellent value package deals from $431 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

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