Pine Island Vacations from $473

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $781, price is now $473 per person
$473
per person
Dec 15 - Dec 18
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Amazing stay. Great food, great bed, great staff

Reviewed on Nov 5, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,064, price is now $1,153 per person
$1,153
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
Beautiful hotel ! Smells so good in lobby .. room a clean and nice

Reviewed on Nov 3, 2025

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,668, price is now $941 per person
$941
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.8/10 Excellent! (1,002 reviews)
Great location clean rooms your site should offer park views we had a view of the building across the street

Reviewed on Oct 20, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,648, price is now $1,023 per person
$1,023
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Every time we travel to NYC we stay here. Staff and location are perfect. Everything is walkable and safe. Lobby bar is a hoot and the breakfast is excellent. Rooms are a good size, clean and upscale.

Reviewed on Nov 6, 2025

Hilton Garden Inn New York/West 35th Street

Hilton Garden Inn New York/West 35th Street

3 out of 5
Manhattan
Save 100% on your flight
Price was $974, price is now $607 per person
$607
per person
Jan 17 - Jan 24
found 8 hours ago
Roundtrip flight included
Burbank (BUR) to New York (NYC)
9/10 Wonderful! (2,935 reviews)
Great staff, clean and close to most things

Reviewed on Nov 5, 2025

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Discover the most popular places to visit in Pine Island

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.

Pine Island Town Park

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.

Scenic Farms Golf Course

Pine Island Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6, Middletown, NY
Fully refundable
$101 nightly
The price is $119 total per night from Dec 3 to Dec 4
$119 total
Dec 3 - Dec 4
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Enjoyed my stay the rooms were very clean and nice

Reviewed on Nov 5, 2025

Sleep Inn & Suites Middletown - Goshen
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
$95 nightly
The price is $117 total per night from Nov 16 to Nov 17
$117 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Nice and quiet

Reviewed on Nov 3, 2025

Hampton Inn Harriman Woodbury
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

3 out of 5
120 Rtes 6 & 209, Matamoras, PA
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $99 total per night from Nov 30 to Dec 1
$99 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Our bathroom smelt was urine and there was no fan. There was no conditioner, weird. I felt like they were trying to cut corners at every angle to save a dollar.

Reviewed on Oct 24, 2025

Best Western Hunt's Landing Hotel Matamoras/Milford
See all 625 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

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 $473 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.

Explore a world of travel with Expedia

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