Pine Island Vacations from $216

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Your Pine Island Vacation

When a city escape is calling, answer it with a Pine Island vacation package. With all your travel needs worked out before you leave, all you need to do here is concentrate on having fun. Love to start exploring your surroundings? Warwick Valley Winery and Distillery, Demarest Hill Winery and Frederick Francks Pacem in Terris are just a few of the leading places to visit during a trip to Pine Island. Whoever you're escaping with and whatever your budget, your ultimate Pine Island vacation is just clicks away with Expedia.

The Latest Pine Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
Topping Rose House
INNSiDE by Meliá New York Nomad
NobleDEN Hotel
The Towers at Lotte New York Palace
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Discover the most popular places to visit in Pine Island

Pine Island Hotel Deals

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $120 total per night from Jan 25 to Jan 26
$120 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,031 reviews)
nearby woodbury premium outlets, free breakfast, spacious room However

Reviewed on Jan 11, 2026

Hampton Inn Harriman Woodbury
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
$98 nightly
The price is $116 total per night from Feb 2 to Feb 3
$116 total
Feb 2 - Feb 3
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Great

Reviewed on Jan 8, 2026

Sleep Inn & Suites Middletown - Goshen
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place Chester NY
Fully refundable
$90 nightly
The price is $106 total per night from Jan 22 to Jan 23
$106 total
Jan 22 - Jan 23
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Yankee the hotel manager was great. Elevator was out of order but it was still amazing. She was so lovely and accommodating. The place was under construction but rooms were clean and spacious and pool and gym were nice

Reviewed on Jan 1, 2026

Holiday Inn Express Hotel & Suites Chester by IHG
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.

Find the Best Pine Island Vacation Packages

Things to do in and around Pine Island

Pine Island is perfect for outdoor enthusiasts seeking adventure and scenic beauty. Visitors can enjoy a variety of activities, including exploring recreational areas, playing golf, and fishing at the pier. Island hopping offers a unique experience, while the local beaches provide a relaxing getaway. Don't miss the chance to engage in fun activities at game tables and savor the natural beauty of this charming destination.

Shopping

For local shopping, visit Soons Orchards, just 8 miles away, offering a charming market vibe. If you're up for a drive, the Galleria at Crystal Run, 12 miles away, provides a lively shopping experience with entertainment options, while Monroe Federal Plaza Shopping Center, 15 miles away, features family-friendly stores.

Recreation

Enjoy a round of golf at Scenic Farms Golf Course, where the serene outdoor vibes enhance your game. Experience the energetic atmosphere at The Rock Sports Complex, perfect for sports enthusiasts. For a touch of culture and entertainment, catch a show at Paramount Theatre, ideal for family outings.

Adventure

Experience thrilling rides at Mountain Creek Waterpark, located 8 miles from Pine Island, perfect for family fun. Soar through the treetops at Zoom Ziplines, also 8 miles away, for an unforgettable outdoor adventure. Hit the slopes at Surface Ski Lift, 8 miles from town, for an exhilarating skiing experience.

Nightlife

Pine Island offers a laid-back nightlife with cozy bars and local hangouts. Enjoy live music at the Pine Island Tap House or unwind at the rustic ambiance of the Pine Island Pub. Whether you prefer a lively crowd or a quiet evening, there's something for everyone.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Pine Island

Pine Island is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Explore local attractions like lakes, state parks, and urban parks that offer a variety of experiences. Don't miss the island views, Bird Island, Pine Island Beach Park, and the Pine Island Shopping Center for a well-rounded visit. Be sure to check out the Pine Island map to navigate your way around this beautiful destination.

  • Pine Island Town Park: Enjoy a serene day at Pine Island Town Park, where you can relax on the beach and soak up the sun. With its beautiful outdoor vibes, this park is perfect for picnics, leisurely strolls, and family gatherings amidst nature.
  • High Point State Park: Adventure awaits at High Point State Park, located 11 miles from Pine Island. Experience breathtaking scenery while hiking, biking, or simply enjoying the great outdoors. The park's diverse landscapes provide a perfect backdrop for outdoor enthusiasts.
  • Frederick Franck's Pacem in Terris: Just 5 miles away, Frederick Franck's Pacem in Terris offers a unique sculpture garden experience. Wander through beautifully crafted sculptures in a tranquil outdoor setting, making it a wonderful spot for families and art lovers alike.

Best time to go to Pine Island

The best time to visit Pine Island can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Pine Island falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Pine Island falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January27.5°F (-2.5°C)Light RainMostly SunnyAverageSlightly Low
February29.5°F (-1.4°C)Light RainMostly CloudySlightly HighSlightly Low
March37.0°F (2.8°C)Light RainMostly SunnySlightly HighSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnySlightly HighAverage
May59.0°F (15.0°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageAverage
July73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
August71.4°F (21.9°C)Light RainMostly SunnyAverageSlightly High
September64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
October53.4°F (11.9°C)Light RainMostly SunnySlightly LowSlightly High
November41.4°F (5.2°C)Light RainMostly SunnySlightly LowAverage
December33.6°F (0.9°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Pine Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Pine Island during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Pine Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Warwick Valley Winery and Distillery, Mount Peter Ski Area and Castle Fun Center

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Frequently asked questions

How much does a Pine Island vacation package cost?
You can grab a vacation package to this top destination from $216 on Expedia. But how much your vacation to Pine Island costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Pine Island?
If you're hoping to snag a cheap Pine Island vacation package, consider planning a trip in November, December and January. You'll generally find better prices on flights and hotels during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Pine Island?
The ideal length of your Pine Island vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to visit all the major sights and explore some hidden treasures along the way.
How to find the best Pine Island package deals?
Finding a cheap Pine Island package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most economical Pine Island package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pine Island vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can personalize your Pine Island escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Pine Island?
If you're planning a spur-of-the-moment Pine Island adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Pine Island vacation packages?
Jet off on your dream escape to Pine Island with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.