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.
Night Hotel Broadway
Manhattan
Price was CA $1,132, price is now CA $765 per person
CA $765
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (3,217 reviews)
It was a very cute and comfortable hotel. It was very clean! I would definitely stay here again.
Reviewed on Jun 29, 2026
NobleDEN Hotel
Manhattan
Price was CA $3,726, price is now CA $2,235 per person
CA $2,235
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,615 reviews)
Great little find, good location. Clean and decent size rooms for NYC
Reviewed on Jun 29, 2026
1 Hotel Brooklyn Bridge
Price was CA $4,026, price is now CA $2,628 per person
CA $2,628
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,000 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
Manhattan
Price was CA $6,971, price is now CA $4,592 per person
CA $4,592
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (645 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
The Wall Street Hotel
Manhattan
Price was CA $2,681, price is now CA $1,792 per person
CA $1,792
per person
Sep 10 - Sep 13
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (695 reviews)
Amazing! Loved my stay there. The hotel was a 10/10.
Reviewed on Jun 29, 2026
Pine Island Hotel Deals
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $174 per night from Jul 28 to Jul 29
CA $174
CA $206 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,044 reviews)
"The room and property were super clean!"
Reviewed on Jun 29, 2026
Best Western Hunt's Landing Hotel Matamoras/Milford
120 Rtes 6 & 209 Matamoras PA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 12 to Jul 13
CA $167
CA $182 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Wonderful front desk \. Super nice guy. Room was nice for a quick overnight as we needed a place to stop and sleep."
Reviewed on Jun 29, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 26 to Jul 27
CA $174
CA $205 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Clean"
Reviewed on Jun 29, 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
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
