Pleasant Valley Vacation Packages 2026 from $360

Pleasant Valley flight + hotel vacation packages

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

it's a good thing

$360

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Houston (HOU) to Newburgh (SWF)

This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and luggage storage are also on offer.

Sleep Inn & Suites Middletown - Goshen

Save 100% on your flight

$383

per person

May 7 - May 12

found 14 hours ago

Roundtrip flight included

Cleveland (CLE) 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.

Buttermilk Falls Inn

Save 100% on your flight

$725

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Houston (HOU) to Newburgh (SWF)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

The Gables of Rhinebeck Inn

Rhinebeck Village

Save 100% on your flight

$587

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Houston (HOU) to Newburgh (SWF)

Free self parking is available and the guesthouse's front desk is staffed around-the-clock. WiFi in public areas is free. A garden and luggage storage are also provided.

Beekman Arms Hotel

Rhinebeck Village

$413

per person

Apr 8 - Apr 11

found 1 day ago

Roundtrip flight included

Houston (HOU) to Newburgh (SWF)

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.

Top Pleasant Valley hotels deals

Courtyard by Marriott Poughkeepsie

2641 South Road/Route 9 Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$119 total

Mar 15 - Mar 16

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.

Pet friendly

Free WiFi

Hampton Inn & Suites Poughkeepsie

2361 South Rd Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Mar 13 - Mar 14

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

Residence Inn by Marriott Kingston

800 Frank Sottile Boulevard Kingston NY

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$132 total

Mar 2 - Mar 3

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

Wildflower Farms, Auberge Collection

2702 Main St Gardiner NY

$947 nightly

$1,061 total

Mar 3 - Mar 4

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

Hampton Inn Kingston

1307 Ulster Ave Kingston NY

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$128 total

Mar 4 - Mar 5

Total with taxes and fees

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 buffet breakfast and free self parking.

Pool

Breakfast included

DoubleTree by Hilton Poughkeepsie Convention Center

40 Civic Center Plz Poughkeepsie NY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$119 total

Mar 1 - Mar 2

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. 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

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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 $360. 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.