Pleasant Valley Vacation Packages 2025/2026 from $288

Pleasant Valley flight + hotel vacation packages

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

Holiday Inn Express & Suites Montgomery by IHG

$288

per person

Jan 23 - Jan 27

found 20 hours ago

Roundtrip flight included

Houston (IAH) to Newburgh (SWF)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-in, and conference space. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Sleep Inn & Suites Middletown - Goshen

$439

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Newburgh (SWF)

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

Holiday Inn Express & Suites Middletown - Goshen by IHG

Save 100% on your flight

$527

per person

Jan 23 - Jan 27

found 20 hours ago

Roundtrip flight included

Houston (IAH) to Newburgh (SWF)

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

Holiday Inn Express Hotel & Suites Chester by IHG

$347

per person

Jan 23 - Jan 27

found 20 hours ago

Roundtrip flight included

Houston (IAH) to Newburgh (SWF)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.

Courtyard by Marriott Newburgh Stewart Airport

$631

per person

Feb 12 - Feb 17

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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.

Top Pleasant Valley hotels deals

Best Western Plus Kingston Hotel And Conference Center

503 Washington Ave Kingston NY

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Nov 26 - Nov 27

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Pet friendly

Hampton Inn & Suites Poughkeepsie

2361 South Rd Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$115 total

Nov 29 - Nov 30

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

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

915 Union Ave New Windsor NY

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$118 total

Dec 1 - Dec 2

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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$99 total

Nov 24 - Nov 25

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A picnic area, laundry facilities, and barbecue grills are also on offer.

Breakfast included

Pet friendly

Wildflower Farms, Auberge Collection

2702 Main St Gardiner NY

$921 nightly

$1,032 total

Dec 18 - Dec 19

Total with taxes and fees

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.

Pool

Spa

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$150 total

Nov 23 - Nov 24

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

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

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 $288. 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.