Book Exclusive Pleasant Valley Vacation Packages
Pleasant Valley flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Newburgh Inn
Price was CA $527, price is now CA $503 per person
CA $503
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a conference center. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Sleep Inn & Suites Middletown - Goshen
Price was CA $665, price is now CA $579 per person
CA $579
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Top Pleasant Valley hotels deals
Hampton Inn & Suites Poughkeepsie
2361 South Rd Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $139 per night
CA $139
CA $161 total
Jan 30 - Jan 31, 2026
includes taxes & fees
Book a stay at this golf hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Casperkill Golf Club and Bananas Comedy Club are located nearby.
Pool
Breakfast included
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
CA $188 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bananas Comedy Club and Casperkill Golf Club are located nearby.
Pool
Pet-friendly
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
915 Union Ave New Windsor NY
Free cancellation
Reserve now, pay when you stay
Book a stay at this business-friendly hotel in New Windsor. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Residence Inn by Marriott Kingston
800 Frank Sottile Boulevard Kingston NY
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $175 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hudson Valley Mall and Robert E. Post Memorial Park are located nearby.
Wildflower Farms, Auberge Collection
2702 Main St Gardiner NY
The price is CA $1,672 per night
CA $1,672
CA $1,932 total
Jan 8 - Jan 9, 2026
includes taxes & fees
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery are located nearby.
Courtyard by Marriott Poughkeepsie
2641 South Road/Route 9 Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $146 total
Jan 14 - Jan 15, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Locust Grove and McCann Golf Course are located nearby.
Free WiFi
Restaurant
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See all available properties in Pleasant Valley
View all propertiesLowest 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.
Popular places to visit
Innisfree Garden
Explore the great outdoors at Innisfree Garden, a lovely green space in Pleasant Valley. Wander the riverfront in this family-friendly area.
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.
Pleasant Valley Vacations
Before you fly off to Pleasant Valley on a whim, take some time to learn a few facts about it.
From downtown Poughkeepsie, you'll need to head east for 7 miles (11 kilometers) to get to this neighborhood.
Last time they counted, the population of Poughkeepsie was 33,000.
Places to visit in Pleasant Valley
The wider region offers plenty of opportunities for outdoor activities. Why not make plans to go snowboarding while you're here? If you're really eager to create some special vacation memories, throw skiing on your must-do list too.Where do you fly into for Pleasant Valley?
If you're heading to Pleasant Valley, the closest terminal is Bradley International Airport (BDL). It's around 60 miles (97 kilometers) east from the main streets. Select an in-flight movie, get comfortable and you'll be landing before you know it.Frequently asked questions
Photos of local treasures
Browse Pleasant Valley vacation photos for more inspiration
