Pine Island Vacations from $791

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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.

33 Hotel, New York City, Seaport

Manhattan

Save 100% on your flight

$791

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,005 reviews)

Better amenities for the bathroom. Great staff on the check-out. JR was amazing. -- room comf=ort and design was great.

Reviewed on Oct 5, 2026

Lotte New York Palace

Manhattan

$1,350

per person

Dec 13 - Dec 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (2,266 reviews)

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$1,094

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (3,361 reviews)

The location is fantastic right on Restaurant Row and a block from Times Square. The hotel lobby is beautiful and the staff was pleasant. For the exorbitant price I paid extra to be able to have my family all in one room with a pull-out couch, the room was pretty tight. The bathroom is modern frosted glass which is nice, but it's not super bright so it wakes people up and the walls are somewhat open so you can hear everything. The shower had great water pressure at least. The walls and doors are thin so you can hear the next room in yours and you can hear everything from every room in the halls. The breakfast had a ton of options and was pretty good too. Being one night, it was acceptable but I wouldn't do a long stay here if you're a family. They did hold our luggage in storage till our room was ready but held $85 for it. The Chromecast was out in the hotel so we couldn't stream apps and could only watch live channels. There is a place to drop-off out front, which is a bonus. Don't believe the listing, though, as there is no on-site parking and the garage they recommended fleeced me extra for having a truck even though I paid for that online beforehand. The subway was only a couple blocks down so fairly easy for transportation. Lots to do in the immediate area and pretty walkable. Overall, location, access, and breakfast are the best parts and it's good for one night.

Reviewed on Oct 5, 2026

Radio Hotel

Manhattan

Save 100% on your flight

$877

per person

Dec 5 - Dec 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

8.4/10 Very Good! (2,416 reviews)

1 Hotel Brooklyn Bridge

Save 100% on your flight

$2,263

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

9/10 Wonderful! (1,010 reviews)

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Stay near popular Pine Island attractions

Pine Island Town Park

Explore the great outdoors at Pine Island Town Park, a lovely green space in Pine Island. Discover the area's mountain views and seek out the ski slopes.

See properties

Scenic Farms Golf Course

Enjoy a round of golf in Pine Island at Scenic Farms Golf Course. Discover the area's mountain views and seek out the ski slopes.

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Pine Island Hotel Deals

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

Fully refundable

$102 nightly

$120 total

Nov 1 - Nov 2

Total with taxes and fees

Best Western Hunt's Landing Hotel Matamoras/Milford

120 Rtes 6 & 209 Matamoras PA

Fully refundableReserve now, pay when you stay

$121 nightly

$132 total

Nov 1 - Nov 2

Total with taxes and fees

8.4/10 Very Good! (1,006 reviews)

"We very much enjoyed our stay at this location. The staff was efficient and professional, our room was very clean and fresh smelling, the bed was comfortable and our room was quiet. The breakfast options were great and the host kept everything refilled as necessary. It's also in a good location. ..."

Reviewed on Oct 5, 2026

Sleep Inn & Suites Monroe - Woodbury

1 Sleep Way Monroe NY

Fully refundable

$110 nightly

$124 total

Oct 27 - Oct 28

Total with taxes and fees

See all 681 properties in Pine Island

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	27.5°F (-2.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.5°F (-1.4°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
April	48.4°F (9.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	59.0°F (15.0°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Average
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
August	71.4°F (21.9°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	64.6°F (18.1°C)	Light Rain	Mostly Sunny	Average	Average
October	53.4°F (11.9°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	41.4°F (5.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	33.6°F (0.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average

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 $791 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.