
Pleasant Valley Holidays
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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.
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

Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 7 Dec to 8 Dec
AU$167
7 Dec - 8 Dec
includes taxes & fees
7.4/10 Good! (1,008 reviews)
Room was good, staff pleasant. The cancelled free breakfasts adding a daily charge but since i booked before then i received free breakfast coupons for each morning. Have to check every BW visit in future though.
Reviewed on 26 Nov 2025

Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 5 Dec to 6 Dec
AU$176
5 Dec - 6 Dec
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
The staff was very nice and accommodating. The room was perfect and the bed was super comfortable. Will stay again if in the area.
Reviewed on 26 Nov 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 3 Dec to 4 Dec
AU$180
3 Dec - 4 Dec
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
The room was very clean and the staff was very nice. The only complaint was the TV - it is small and you have to click through every channel to see what's on as there is no guide. Also, there is no coffee pot in the room, but that's just a minor thing.
Reviewed on 24 Nov 2025
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.
What to do in Pleasant Valley

Llama/Alpaca Hike and Farm Tour
AU$103
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.













