Pine Island Vacations from $746

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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.
Hotel 27 by LuxUrban
1 Hotel Brooklyn Bridge
Hotel Riu Plaza New York Times Square
NobleDEN Hotel
Hotel Seville Nomad, in the Unbound Collection by Hyatt
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Discover the most popular places to visit in Pine Island

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 refundableReserve now, pay when you stay
$111 nightly
The price is $131 total per night from Sep 29 to Sep 30
$131 total
Sep 29 - Sep 30
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
"I liked it all. The young lady at the front"

Reviewed on Sep 8, 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
$118 nightly
The price is $145 total per night from Sep 21 to Sep 22
$145 total
Sep 21 - Sep 22
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Staff, property and location were excellent."

Reviewed on Sep 8, 2025

Hampton Inn Harriman Woodbury
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Sep 21 to Sep 22
$140 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (829 reviews)
Great family wacape
"Great escape to Legoland. Great area for family fun"

Reviewed on Sep 8, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
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.

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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 $746 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

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.