Pine Island Vacations from $390

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $771, price is now $390 per person
$390
per person
Oct 28 - Nov 1
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (9 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.

Reviewed on Aug 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,221, price is now $1,207 per person
$1,207
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug 21, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
Price was $1,035, price is now $572 per person
$572
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (506 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.

Reviewed on Aug 14, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $729, price is now $404 per person
$404
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,397, price is now $788 per person
$788
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (561 reviews)
Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound

Reviewed on Aug 18, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pine Island
View all trips

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
$103 nightly
The price is $122 total per night from Sep 23 to Sep 24
$122 total
Sep 23 - Sep 24
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Had a great time, free breakfast and wifi was excellent and useful for my family. Beds large enough for parents and children."

Reviewed on Aug 20, 2025

Sleep Inn & Suites Middletown - Goshen
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 Aug 28 to Aug 29
$140 total
Aug 28 - Aug 29
Total with taxes and fees
9.2/10 Wonderful! (793 reviews)
"We were stranded in Middletown, NY for 3 days due to a tire issue (waiting on special order tire from Sams Club) and it couldn't have been at a better hotel. Was a very pleasant stay."

Reviewed on Aug 20, 2025

La Quinta Inn & Suites by Wyndham 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
$110 nightly
The price is $135 total per night from Sep 2 to Sep 3
$135 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"The hotel is in a busy BUT very secluded being in the back of the main road. It is beyond clean. Room was spacious and very comfortable. Breakfast was good. Coffee and tea available 24 hrs. Staff very nice and knowledgeable. Only complaint, you do need a car to go to the outlets. It says walking ..."

Reviewed on Aug 15, 2025

Hampton Inn Harriman Woodbury
See all 616 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pine Island vacation package cost?
You can grab a vacation package to this top destination from $390 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.