Pine Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Top Pine Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
CA $2,926
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet
Reviewed on Aug 16, 2026
Seven Beach Lane
CA $1,314
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
Night Hotel Broadway
Manhattan
CA $1,046
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.4/10 Good! (3,437 reviews)
The Night Hotel is overall a nice place to stay. It is in a great location and the prices are good for a stay in NYC. It is a bit dated and the room (Gold King Bed) was pretty much just the bed and small writing desk. If you are looking for a solid spot for just sleeping and leaving in the morning, this is your place. If you were planning on spending extended periods of time in your room, I might try elsewhere. The biggest highlight was the staff, very pleasant to interact with, making you feel welcome.
Reviewed on Aug 17, 2026
Ready to book your vacation to Pine Island?
Pine Island Hotel Deals
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
CA $147
CA $174 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,136 reviews)
"The room was clean and came with a microwave and fridge. The beds were very comfortable and the room was spacious. The breakfast was pretty good and the 24hr coffee, tea, and hot chocolate was nice. Great location too."
Reviewed on Aug 17, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
CA $176
CA $208 total
Aug 23 - Aug 24
includes taxes & fees
LEGOLAND Hotel NEW York
1 LEGOLAND BLVD Goshen NY
CA $282
CA $502 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very good! (95 reviews)
"Great stay with my family of 5 ! Kids had blast! One night stand , overall great experience! Thanks Legoland New York!"
Reviewed on Aug 16, 2026
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.
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.
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.
Frequently asked questions
How much does a Pine Island vacation package cost?
Offering excellent value package deals from CA $995 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?
- 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.
- 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.
- 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.
- 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.
