Pleasant Valley Vacation Packages 2026 from $433

Pleasant Valley flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Homewood Suites Stewart Airport

$433

per person

Feb 25 - Mar 2

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. Free WiFi in public areas, a lobby fireplace, and express check-out are also on offer.

Courtyard by Marriott Newburgh Stewart Airport

Save 100% on your flight

$502

per person

Feb 18 - Feb 24

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

$453

per person

Mar 4 - Mar 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Wildflower Farms, Auberge Collection

Save 100% on your flight

$1,971

per person

Mar 16 - Mar 19

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Hampton Inn & Suites Newburgh Stewart Airport

$463

per person

Feb 18 - Feb 24

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to Newburgh (SWF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Pleasant Valley hotels deals

Hampton Inn & Suites Poughkeepsie

2361 South Rd Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$118 total

Jan 23 - Jan 24, 2026

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$117 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

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

$101 nightly

$114 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a computer station, and luggage storage are also offered.

Pool

Pet friendly

Residence Inn by Marriott Kingston

800 Frank Sottile Boulevard Kingston NY

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$128 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Pet friendly

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$107 total

Jan 18 - Jan 19, 2026

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Free WiFi

Restaurant

Hampton Inn by Hilton New Paltz

4 South Putt Corners Road New Paltz NY

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$137 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

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

Just a sneak peak at a most wonderful gem of a garden...

Innisfree Garden

5/5(1 review)

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.

Frequently asked questions

How much are vacation packages to Pleasant Valley?

Your travel dreams can be realized in Pleasant Valley for as little as $433. 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 70 mi 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 60 mi east of the downtown area. You could also choose to fly into Tweed - New Haven Regional Airport (HVN) (60 mi away from central Pleasant Valley) or Stewart Intl. Airport (SWF) (20 mi 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.