Pleasant Valley Holidays from £627

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Your Pleasant Valley Holiday

The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley holiday package. Stay in the neighbourhood 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 holiday is easy with Expedia.

Top Pleasant Valley Flight + Hotel 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
8 Oct - 15 Oct
found 24 hours ago
Return flight included
London (LON) to Newburgh (SWF)
7.6/10 Good! (464 reviews)
Good pricing for the nice quality rooms

Reviewed on 27 Jul 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
21 Oct - 24 Oct
found 1 day ago
Return flight included
London (LHR) to Newburgh (SWF)
9.2/10 Wonderful! (916 reviews)
Booked this hotel because it had a shuttle to the airport; when I checked in I was told there would be no shuttle from July 18th to September 30th. Had to pay $35 to Uber to the airport.☹️

Reviewed on 2 Aug 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
21 Oct - 24 Oct
found 1 day ago
Return flight included
London (LHR) to Newburgh (SWF)
8.2/10 Very Good! (654 reviews)
We stayed at this hotel because it said they had a pool. The pool was closed the whole time. They should have put this on their website. They said they clean rooms every other day. However, I had to ask at the front desk on the every other day and she said we "requested" it. It took forever for someone to come to the front desk and to answer the phone many times.. We won’t be staying at this hotel again

Reviewed on 21 Jul 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
21 Oct - 24 Oct
found 1 day ago
Return flight included
London (LHR) to Newburgh (SWF)
9.2/10 Wonderful! (1,001 reviews)
Buen desayuno. Habitacion limpia y comoda.

Reviewed on 25 Jul 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
8 Oct - 15 Oct
found 24 hours ago
Return flight included
London (LON) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
The ad on Expedia said, "Breakfast included," except breakfast was a bag of trail mix and 2 granola bars. At 8:30 or 9am, I went to get just a little more coffee but it was all gone. Otherwise, everything was fine.

Reviewed on 28 Jul 2025

Pleasant Valley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
1,150
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Millbrook Vineyards and Winery, Wings Castle and Chance Theatre

Top hotels in Pleasant Valley

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 £95 per night from 17 Aug to 18 Aug
£95
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Easy access, cleanliness, excellent room. Very good breakfast."

Reviewed on 1 Aug 2025

Holiday Inn Express Poughkeepsie by IHG
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is £89 per night from 3 Aug to 4 Aug
£89
3 Aug - 4 Aug
includes taxes & fees
7.4/10 Good! (458 reviews)
"Would go back"

Reviewed on 30 Jul 2025

Wingate by Wyndham Fishkill
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 £111 per night from 10 Aug to 11 Aug
£111
10 Aug - 11 Aug
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Nice hotel
"It was fine, the breakfast was good. They varied the options every day"

Reviewed on 31 Jul 2025

Best Western Plus Kingston Hotel And Conference Center
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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Family Friendly Holidays

What to do in Pleasant Valley

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

£50
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Pleasant Valley

Frequently asked questions

Why should I book my Pleasant Valley holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Pleasant Valley holiday. You'll always land the best deals around, but when you bundle your accommodation, airfares and/or hire car into a holiday package, you can save even more. Looking to truly make the most of your escape? Add some exciting tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so there's no need to worry if your travel plans change. Head over to our Customer Service Portal link to discover more.
When is the best time of year to holiday in Pleasant Valley?
Pleasant Valley gets busy in June, July and August. If you're not into large crowds and prefer a quieter pace, lock in your getaway for December, January and February. Arrange your visit to Pleasant Valley based on what kind of adventure you're looking for. January is the coolest time of year, when daytime temperatures average -2ºC. In July, the warmest month, expect temperatures of around 23ºC during the day.
What is the top hotel for my holiday in Pleasant Valley?
DoubleTree by Hilton Hotel Nanuet is an ideal base for a wonderful escape in Pleasant Valley, offering all the amenities you'll need and more.
How do I get a cheap holiday to Pleasant Valley?
Our Pleasant Valley holidays mean plenty of savings for the savvy wanderer. For the best deal, simply combine your hotel, flights and extras (including activities). But cheap prices are just the beginning of your next unforgettable adventure. When you book with Expedia, you'll have more than 400 air carriers and 321,000 properties around the globe to choose from. No matter your budget, there's a holiday here that's perfect for you. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Pleasant Valley holiday?
Offering leading attractions such as Culinary Institute of America and Marist College, a holiday in Pleasant Valley is full of exciting things to do and see. Vassar College and Vanderbilt Mansion National Historic Site are a couple of other sights worth exploring.
What is the best area to stay in when on holiday in Pleasant Valley?
An escape to Pleasant Valley isn't complete without stopping by Innisfree Garden. Why not book a stay close to this great attraction?
Do I need a visa for my Pleasant Valley holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the purpose of your visit, whether it be for tourism or business, will determine if you need a visa for Pleasant Valley. Also check that your passport is up to date and has a minimum of six months validity remaining after your return date. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Pleasant Valley holiday?
First, think about the type of activities planned during your trip to Pleasant Valley and take versatile pieces that you can mix and match. For fashion inspiration or information on any dress codes, browse a few style blogs or social media accounts. Have a look at the local weather forecast so you can pack your bags accordingly. The warmest month in Pleasant Valley is July, with average daytime temperatures of 23ºC. If you're visiting during the coolest month of January, the mercury averages -2ºC during the day.
What does an Expedia Pleasant Valley holiday include?
Flights, hotels and a cool set of wheels for all your fun road trip adventures. Simply select your preferred bundle and get access to incredible deals. Once you've made your booking, add on a couple of tours and activities and watch your savings stack up. When it comes to planning your Pleasant Valley break, you're in control! Explore a wide range of property types and pick one that matches your travel needs. The most in-demand holiday rentals here are private holiday homes and apartments. With Expedia, it's easy to tailor your Pleasant Valley escape however you want.
Does Expedia offer Book Now, Pay Later Pleasant Valley holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on your bank balance. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
  • No-deposit holidays: When you stumble on an awesome deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Pleasant Valley Expedia holiday?
Expedia has access to more than 400 partner airlines globally, so you certainly can. Just select your preferred carrier and put together your ideal Pleasant Valley escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.