Book Exclusive Pleasant Valley Vacation Packages

Choose one or more items to build your trip:

Pleasant Valley flight + hotel packages

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
Mar. 10 - Mar. 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
La Quinta Inn & Suites by Wyndham Middletown

La Quinta Inn & Suites by Wyndham Middletown

2.5 out of 5
per person
Feb. 27 - Mar. 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Feb. 14 - Feb. 18
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

2 out of 5
per person
Mar. 27 - Mar. 30
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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.

Residence Inn by Marriott Middletown Goshen

3 out of 5
per person
Feb. 27 - Mar. 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
Stay at this 3-star business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.

Top Pleasant Valley hotels deals

HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $160 total
includes taxes & fees
30 Jan - 31 Jan
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blodgett Memorial Library and Van Wyck Homestead Museum are located nearby.
Pool
Hot tub
Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

3.5 out of 5
14 Schuyler Blvd, Fishkill, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $133 per night
CA $133
CA $149 total
includes taxes & fees
2 Feb - 3 Feb
Book a stay at this business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Van Wyck Homestead Museum and Blodgett Memorial Library are located nearby.
Pool
Breakfast included
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,292 per night
CA $1,292
CA $1,510 total
includes taxes & fees
9 Jan - 10 Jan
Stay at this 5-star 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
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 $145 per night
CA $145
CA $163 total
includes taxes & fees
14 Jan - 15 Jan
Stay at this 3-star business-friendly 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 Bananas Comedy Club and Casperkill Golf Club are located nearby.
Pool
Breakfast included
DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $152 per night
CA $152
CA $176 total
includes taxes & fees
14 Jan - 15 Jan
Stay at this 4-star 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 McCann Ice Arena and Mid-Hudson Civic Center are located nearby.
Parking included
Free WiFi
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Free cancellation
Reserve now, pay when you stay
The price is CA $207 per night
CA $207
CA $232 total
includes taxes & fees
26 Jan - 27 Jan
Stay at this 3-star business-friendly hotel in Hyde Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Richard L. Skimin Memorial Baseball Field and Home of Franklin D. Roosevelt National Historic Site are located nearby.
Breakfast included
Pet-friendly
Don't see what you're looking for?
See all available properties in Pleasant Valley
View all properties
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

Explore the great outdoors at James Baird State Park, a lovely green space in Pleasant Valley. Check out the shops and top-notch restaurants 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 $530. 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