Pleasant Valley Vacation Packages 2026

Top Pleasant Valley hotels deals

Hyatt Place Poughkeepsie / Hudson Valley

2165 South Road Poughkeepsie NY

$101 nightly

$117 total

Sep 7 - Sep 8

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

Breakfast included

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$202 total

Aug 31 - Sep 1

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.

Breakfast included

Pet friendly

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

Free Cancellation

$101 nightly

$117 total

Sep 7 - Sep 8

Total with taxes and fees

A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, a snack bar/deli, and a picnic area are also on offer.

Breakfast included

Parking included

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$90 total

Aug 31 - Sep 1

Total with taxes and fees

A nightclub and a gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a lobby fireplace, and a computer station are also offered.

Parking included

Free WiFi

DoubleTree by Hilton Poughkeepsie Convention Center

40 Civic Center Plz Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$143 total

Aug 31 - Sep 1

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 8 conference rooms, free WiFi in public areas, and express check-out. Free self parking, a coffee shop, and a terrace are also offered.

Parking included

Free WiFi

SureStay Plus Hotel by Best Western Highland Poughkeepsie

3423 US Highway 9W Highland NY

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Aug 30 - Aug 31

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

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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.

Stay near popular Pleasant Valley attractions

Innisfree Garden

10.0/10 (2 reviews)

Explore the great outdoors at Innisfree Garden, a lovely green space in Pleasant Valley. Wander the riverfront in this family-friendly area.

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Frequently asked questions

How much are vacation packages to Pleasant Valley?

Your travel dreams can be realized in Pleasant Valley for as little as . 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.