Book Exclusive Pleasant Valley Vacation Packages

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Pleasant Valley flight + hotel packages

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Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
Price was CA $697, price is now CA $649 per person
CA $649
per person
Mar 24 - Mar 27
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodbury Common Premium Outlets and Museum Village are located nearby.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was CA $829, price is now CA $756 per person
CA $756
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was CA $985, price is now CA $908 per person
CA $908
per person
May 2 - May 6
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was CA $1,221, price is now CA $1,133 per person
CA $1,133
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Stay at this hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hamilton Fish Bridge and National Purple Heart Hall of Honor are located nearby.
Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
Price was CA $1,139, price is now CA $1,058 per person
CA $1,058
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. 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

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $161 total
Feb 19 - Feb 20
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.
Pet-friendly
Free WiFi
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 $167 per night
CA $167
CA $188 total
Mar 1 - Mar 2
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
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $118 per night
CA $118
CA $138 total
Feb 21 - Feb 22
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 McCann Ice Arena and Bardavon 1869 Opera House are located nearby.
Parking included
Free WiFi
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
The price is CA $1,485 per night
CA $1,485
CA $1,737 total
Feb 18 - Feb 19
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 & 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 $122 per night
CA $122
CA $141 total
Feb 20 - Feb 21
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
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 $196 per night
CA $196
CA $221 total
Mar 16 - Mar 17
includes taxes & fees
Book a stay at this 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
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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

Just a sneak peak at a most wonderful gem of a 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 $649. 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

Autumn Homes by the Hillside (Hudson Valley, New York, USA)
Autumn Homes by the Hillside (Hudson Valley, New York, USA)
Just a sneak peak at a most wonderful gem of a garden...