Pine Island Vacations from $263

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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.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,051 reviews)
All was good for my stay and very pleasant

Reviewed on Jun 29, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on Jun 25, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,385 reviews)
We enjoyed the convenience of our stay. Hotel was clean, staff was really helpful.

Reviewed on Jun 30, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (5,584 reviews)
We have been staying at The Empire 1-2 times per year for 15 years to attend the ballet at Lincoln Center. It is a simple walk across the street to the theater, and there are plenty of dining options nearby. We have always been happy with our room, the staff is excellent and gracious. I highly recommend the hotel.

Reviewed on Jun 29, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,004 reviews)
The room was very spacious, comfortable and very clean also. The pool and hot tub, and the bar overlooking it, were nice. The breakfast and dinner buffet were consistently served cold, as the food was placed in sternos that were not turned on. Such an easy thing to get right; maybe staff not trained? The hotel was well located and they had an excellent restaurant, Volpe, on the property.

Reviewed on Jun 29, 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 refundableReserve now, pay when you stay
$92 nightly
The price is $108 total per night from Jul 27 to Jul 28
$108 total
Jul 27 - Jul 28
Total includes taxes and fees
8.4/10 Very Good! (1,009 reviews)
"Peaceful"

Reviewed on Jun 28, 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
$135 nightly
The price is $166 total per night from Jul 7 to Jul 8
$166 total
Jul 7 - Jul 8
Total includes taxes and fees
9/10 Wonderful! (1,003 reviews)
"Liked all aspects of,the property Nothing I didn't like"

Reviewed on Jun 20, 2025

Hampton Inn Harriman Woodbury
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Jul 6 to Jul 7
$109 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (910 reviews)
"The pool is pretty small, but perfect for little kids. The hotel does have a few restaurants within walking distance, which was handy. Friendly and clean stay. The pull out couch was a bit disappointing. It was just a tiny bit larger than a twin."

Reviewed on Jun 26, 2025

Courtyard by Marriott Middletown Goshen
See all 629 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 $263 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.