Pine Island Vacations from $211

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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.
Millennium Hilton New York One UN Plaza

Millennium Hilton New York One UN Plaza

4 out of 5
Manhattan
Price was $489, price is now $211 per person
$211
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.2/10 Very Good! (1,948 reviews)
Rooms left much to be desired. Not a proper placement to room anyone considering rooms were being renovated above which directly affected the plumbing in our room.

Reviewed on Oct 27, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $574, price is now $296 per person
$296
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
clean room, ample parking

Reviewed on Nov 10, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,629, price is now $868 per person
$868
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.8/10 Excellent! (1,012 reviews)
Overall, we loved everything about 1 hotel Brooklyn Bridge. It was a birthday gift trip for my husband, and he enjoyed every minute of our stay. Thank you and we will be back again! Definitely a 5 star hotel and will recommend to my friends.

Reviewed on Nov 9, 2025

The Fifty Sonesta Hotel New York

The Fifty Sonesta Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $472, price is now $257 per person
$257
per person
Feb 2 - Feb 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (1,283 reviews)
Very friendly front desk Team. Easy checkin process.

Reviewed on Nov 11, 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $741, price is now $413 per person
$413
per person
Jan 15 - Jan 18
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.4/10 Very Good! (1,646 reviews)
Electrical outlets by windows in 2011 don’t work.

Reviewed on Nov 12, 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

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 Dec 1 to Dec 2
$117 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Nice and quiet

Reviewed on Nov 3, 2025

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
$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! (1,008 reviews)
clean rooms

Reviewed on Nov 10, 2025

Sleep Inn & Suites Middletown - Goshen
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 627 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 $211 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.