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.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $2,832, price is now CA $1,505 per person
CA $1,505
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (681 reviews)
We celebrated our anniversary with an overnight stay at the Towers & given the cost, had high hopes. The room was spacious & clean with a nice view but the service was sub par. The receptionist was neither friendly nor welcoming when we arrived & a different receptionist ignored us at checkout. The little things matter. There are many luxury hotels in the city & we’ll be staying at another next time.

Reviewed on Jun 25, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,843, price is now CA $2,309 per person
CA $2,309
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Nicely designed hotel with beautiful views. Staff was very nice but service was generally slow.

Reviewed on Jun 28, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $3,163, price is now CA $1,970 per person
CA $1,970
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (650 reviews)
Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel.

Reviewed on Jun 21, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,423, price is now CA $1,533 per person
CA $1,533
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
Great location

Reviewed on Jul 1, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $3,055, price is now CA $1,935 per person
CA $1,935
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
We usually stay at the Ritz but prices were up overall due to the World Cup so we tried this property. It was fantastic and we may have found a new favorite.

Reviewed on Jun 15, 2026

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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 refundable
The price is CA $178 per night from Jul 26 to Jul 27
CA $178
CA $211 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,049 reviews)
"I will never ever stay at this sleeps inn the house keeping service is horrible and the staff hang out at night with their friends. Also a couple of people were outside smoking pot"

Reviewed on Jul 2, 2026

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
The price is CA $167 per night from Jul 5 to Jul 6
CA $167
CA $182 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Room was comfortable for our one night stay. We are seniors and need more issues to be handled. Would have been nice to have a recliner in the room also a walk in shower."

Reviewed on Jun 30, 2026

Best Western Hunt's Landing Hotel Matamoras/Milford
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 $175 per night from Jul 26 to Jul 27
CA $175
CA $207 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Rooms were clean and A/C worked well. Lots of water pressure in the shower. Friendly staff."

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 671 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.
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Stay near popular Pine Island attractions

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.
See properties

Frequently asked questions

How much does a Pine Island vacation package cost?
Offering excellent value package deals from CA $1,505 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.

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