Pine Island Vacation Packages

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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.

Top Pine Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,429 reviews)
Great location! Friendly staff and very clean.

Reviewed on Jul. 6, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul. 17, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (816 reviews)
Quite, good customer service, clean

Reviewed on Jul. 14, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 20 - Aug 27
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
A clean modern hotel. Check in was slow, 15 minutes in a long line. No room until 4.40. Staff very efficient. Comfy bed. Pillows not great. Bathroom very functional. Breakfast, included in room rate, was a feeding frenzy with many options. Packed even at 10am when service stopped! Nice bar also a grab and go mini deli was helpful. If only it was a little less expensive!

Reviewed on Jul. 17, 2025

Ready to book your vacation to Pine Island?

 

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Pine Island Hotel Deals

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
The price is CA $151 per night from Jul 28 to Jul 29
CA $151
CA $178 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (751 reviews)
"The only thing that could be better is the toilet paper hanger."

Reviewed on Jul. 16, 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
The price is CA $174 per night from Jul 27 to Jul 28
CA $174
CA $214 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Nice place. Great staff and good location. Quiet even though it’s right off the highway and it’s conveniently located."

Reviewed on Jul. 9, 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 refundableReserve now, pay when you stay
The price is CA $132 per night from Aug 3 to Aug 4
CA $132
CA $156 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"Everything was good except we were next to elevator so kids knocked an ran on my door when my kids were sleeping. Pools small especially to have someone use it for private swim lessons"

Reviewed on Jul. 17, 2025

Sleep Inn & Suites Middletown - Goshen
See all 635 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pine Island vacation package cost?
Offering excellent value package deals from CA $732 on Expedia, you'll be surprised at how little a vacation to Pine Island costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pine Island?
If you'd like to book a cheap Pine Island vacation package, consider travelling in January, February and March. You'll generally find better prices on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Pine Island?
We recommend planning a Pine Island vacation for around 2 days. This will allow you enough time to check off key attractions including Scenic Farms Golf Course and Frederick Franck's Pacem in Terris, as well as check out neighbourhoods like New Milford and Johnson. You might even be able to slot in a day trip or two beyond Pine Island.
How to find the best Pine Island package deals?
Bagging a cheap Pine Island package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Pine Island package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Pine Island vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can tailor your Pine Island escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Pine Island?
If you have your Pine Island travel dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Pine Island?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Pine Island.
  2. Budget wisely: On top of the price of your accommodations, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Pine Island.
  3. Determine how many days away: Start by listing all the activities and sights you want to get to in Pine Island. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Pine Island vacation package that brings all your bookings together.

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