Pleasant Valley Holidays from AU$2,422

Book a Hotel + Flight or Car together to unlock savings

Photo by louann ohora

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Pleasant Valley Holiday

Reserve a Pleasant Valley holiday package that has only the things you need and nothing you don't. Good for history, families and culture, consider staying in the neighbourhood of Poughkeepsie Waterfront. Like to explore? Marist College, Culinary Institute of America and Vassar College are just three of the top-rated places to visit during your trip to Pleasant Valley. Whatever your travel plans or the size of your budget, organising a tailored Pleasant Valley holiday is easy with Expedia.

The Latest Pleasant Valley Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was AU$2,526, price is now AU$2,422 per person
AU$2,422
per person
29 Sept - 3 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
7.4/10 Good! (520 reviews)
I enjoyed the location. The place was clean and employees were very pleasant

Reviewed on 21 Aug. 2025

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

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

2 out of 5
Price was AU$2,512, price is now AU$2,512 per person
AU$2,512
per person
29 Sept - 3 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Newburgh (SWF)
8.4/10 Very Good! (1,013 reviews)
Staff was super friendly with my 9 year old and I. It was qiuet and we had plenty of room. I would go again any time. NY is a little far away for a weekend trip but I really loved it.

Reviewed on 23 Aug. 2025

Pleasant Valley Holiday

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, Chance Theatre and Wings Castle

Our pick of the best 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 22 May 2025

Get rates
The Lagrange Inn & Extended Stay
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is AU$179 per night from 2 Sept to 3 Sept
AU$179
2 Sept - 3 Sept
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on 21 Aug. 2025

The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is AU$1,828 per night from 23 Sept to 24 Sept
AU$1,828
23 Sept - 24 Sept
includes taxes & fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on 15 May 2025

Wildflower Farms, Auberge Resorts Collection
See all 1,117 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Pleasant Valley

Have you hugged an alpaca today?

Alpaca and Llama Trek in Pleasant Valley

AU$74
per adult
Alpaca and Llama Trek in Pleasant Valley
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

AU$103
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 holiday package cost?
Offering excellent value package deals from AU$2,422 on Expedia, you'll be pleasantly surprised at how much a holiday 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?
Plan your trip for the off-peak season and you're likely to find cheap Pleasant Valley holiday packages. Keep in mind that school holiday periods and major events and festivals can have an impact on prices, so do a little research before you go.
How many days is enough for Pleasant Valley?
For your Pleasant Valley holiday, a few days will be enough to tour all the highlights. Make sure to stop by Innisfree Garden — it's one of the most popular sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some trips from Pleasant Valley.
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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Pleasant Valley holiday as a package?
Expedia holiday 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 personalised Pleasant Valley holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Pleasant Valley.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your hotel will likely be the biggest expense during your trip to Pleasant Valley.
  3. Decide how long to go for: Now that you're up to speed on Pleasant Valley, you can work out the perfect length of your holiday. Create a rough plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Pleasant Valley holiday package that brings all your bookings together.

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