Book Exclusive Pleasant Valley Vacation Packages

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Pleasant Valley flight + hotel packages

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

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

2 out of 5
Price was CA $604, price is now CA $604 per person
CA $604
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
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.

Top Pleasant Valley hotels deals

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $133 per night
CA $133
CA $155 total
Jan 3 - Jan 4, 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

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $161 per night
CA $161
CA $187 total
Jan 6 - Jan 7, 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
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
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 1 - Jan 2, 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.
Breakfast included
Pet-friendly
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
915 Union Ave New Windsor NY
Free cancellation
Reserve now, pay when you stay
Get rates
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.
Pool
Pet-friendly
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
The price is CA $1,669 per night
CA $1,669
CA $1,929 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.
Pool
Spa
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 out of 5
4 South Putt Corners Road New Paltz NY
Free cancellation
Reserve now, pay when you stay
The price is CA $167 per night
CA $167
CA $187 total
Jan 3 - Jan 4, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Samuel Dorsky Museum of Art and Loren Campbell Memorial Field are located nearby.
Pool
Breakfast included
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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.

Popular places to visit

Innisfree 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 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

How much are vacation packages to Pleasant Valley?
Your travel dreams can be realized in Pleasant Valley for as little as CA $604. Our package deals include flights and hotels, and they'll make your booking easy as pie. The only thing you'll have to focus on is having an incredible time.
Where can I get the best vacation package deals for Pleasant Valley?
Travelocity is the place to go to score an awesome Pleasant Valley package deal. Choose from 400 air carriers and 1,000,000 properties worldwide and craft a vacation package that fits your style. With so many options, you have inspiration galore for your next big escape.
Why should I book my Pleasant Valley vacation bundle with Travelocity?
Whether you're searching for the ultimate unplugged getaway or you crave the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to search through hundreds of websites for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available 24/7.
Will I save money on my Pleasant Valley car rental if I bundle it with hotels and flights?
Certainly — combine your car, hotel and flight into a Pleasant Valley vacation package and you'll save a handsome sum. With so many things to do in and around Pleasant Valley, that rental car will make exploring easy. Once you've buckled up, put the stereo on and find your way to Times Square, a well-known sight approximately 113 kilometers from Pleasant Valley.
Which airport is best for Pleasant Valley?
For plenty of visitors, a trip to Pleasant Valley means strolling through arrivals at Bradley Intl. Airport (BDL). This buzzing airport is situated 97 kilometers east of the downtown area. You could also choose to fly into Tweed - New Haven Regional Airport (HVN) (97 kilometers away from central Pleasant Valley) or Stewart Intl. Airport (SWF) (32 kilometers away from central Pleasant Valley).
What is there to do in Pleasant Valley?
While getting off the beaten track is rewarding, you shouldn't ignore the big attractions that make a destination famous. Innisfree Garden and James Baird State Park are just two of them in Pleasant Valley.
Where should I stay when visiting Pleasant Valley?
The Be our guest at The Nest! is the number one choice of many visitors. Book now to avoid missing out.

Photos of local treasures

Browse Pleasant Valley vacation photos for more inspiration

Photo by louann ohora
Photo by louann ohora