Pine Island Holidays from £998

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    Save up to £335 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

Your Pine Island Holiday

When a city escape is calling, answer it with a Pine Island holiday 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 holiday is just clicks away with Expedia.

Top Pine Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
17 Sept - 21 Sept
found 1 day ago
Return direct flight included
London (LON) to New York (JFK)
9.2/10 Wonderful! (3,398 reviews)
The staff was very friendly and helpful. The hotel was very clean. The location was very central to everything. Parking was the only thing that was a bit of a hassle, but expected for Manhattan I guess.

Reviewed on 5 Aug 2025

La Quinta Inn & Suites by Wyndham Times Square South

La Quinta Inn & Suites by Wyndham Times Square South

3 out of 5
Manhattan
per person
20 Oct - 24 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to New York (JFK)
9/10 Wonderful! (1,010 reviews)
I loved it! Would come back and stay here. Walkable and close to everything with good food options everywhere. The parking across the street was easy and discounted when staying at the hotel. They held my luggage before check in and after check out. The staff was so nice, place was clean. Had 0 issues. Definitely worth it and the price is good for the area.

Reviewed on 6 Aug 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
11 Oct - 18 Oct
found 12 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
7.8/10 Good! (1,511 reviews)
We loved the location. What we didn’t like was that there was no refrigerator or microwave in the room. There was also a fight in the room next door to ours and no one checked in to see if we were okay.

Reviewed on 5 Aug 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 23 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on 6 Aug 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
9 Sept - 13 Sept
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,009 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

Pine Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Mountain Creek Ski Resort, Warwick Valley Winery and Distillery and Mount Peter Ski Area

Top hotels in Pine Island

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 £86 per night from 24 Aug to 25 Aug
£86
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Great hotel, Fantastic Breakfast!
"We had a great stay here. The manager was the best (Corlina? Corvina?) Everything was clean and the room was super comfortable. And the breakfast was off the charts! Waffles, eggs, delicious pastries, French toast…. Best breakfast I’ve had at a hotel that was included with the room! The only negative ..."

Reviewed on 4 Aug 2025

Sleep Inn & Suites 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 £117 per night from 2 Sept to 3 Sept
£117
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"I had a wonderful time with my family and friends. People were nice and friendly. Asked for extra items due to longer stay and was accommodated without issue."

Reviewed on 4 Aug 2025

Hampton Inn Harriman Woodbury
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 £108 per night from 24 Aug to 25 Aug
£108
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (775 reviews)
"Place was great have stayed here many times."

Reviewed on 30 Jul 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
See all 613 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

Why should I book my Pine Island holiday with Expedia?
With excellent-value airfares, car hire and hotel options all in one place, Expedia makes booking your Pine Island break easy. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Select from amazing retreats, add your flights and/or a car hire (and maybe also some fun tours and activities!) and score incredible prices. Had a change of plans? Expedia has a flexible cancellation policy for many bookings. To find out more, visit our Customer Service Portal link.
When is the best time of year to holiday in Pine Island?
April, July and August are the busiest months in Pine Island, while November, December and January are generally quieter. To get an idea of the type of weather you can experience, the average daytime temperature in January, the coolest time of year in Pine Island, is -2ºC. The warmest time here is July, when temperatures hit an average of 23ºC.
What is the top hotel for my holiday in Pine Island?
Offering lots of amenities and a cosy place to stay, Holiday Inn & Suites Parsippany Fairfield, an IHG Hotel will make the ideal base for your Pine Island holiday.
How do I get a cheap holiday to Pine Island?
Booking a flight and hotel together with Expedia won't just save precious time — it'll save you money too. A Pine Island holiday makes it a cinch to arrange the perfect trip. With more than 400 airlines throughout the world to select from, finding flights that suit your schedule won't be an issue. In addition to that, we've got over 321,000 hotel options globally to pick from. Now that's what we call choice. Whatever your budget, Expedia puts the world within your reach. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Pine Island holiday?
Offering popular attractions like Mountain Creek Ski Resort and Warwick Valley Winery and Distillery, a holiday in Pine Island promises lots of exciting things to see and do. Applewood Winery and Demarest Hill Winery are two other sights also worth checking out.
Do I need a visa for my Pine Island holiday?
Visa requirements for Pine Island vary based on your nationality and reason for your visit. Be sure to check official government websites to determine if you need a visa for your holiday. They'll give you the most up-to-date information, including details about application procedures and any supporting documentation you may need. Enquire about your visa requirements well in advance to ensure a smooth travel experience. Also make sure your passport has at least six months validity from the date of your return.
What should I wear on my Pine Island holiday?
First, consider the type of activities planned during your holiday in Pine Island and choose versatile pieces that you can mix and match. For fashion inspiration or information on any dress codes, look up a few style blogs or social media accounts.
What does an Expedia Pine Island holiday include?
Hotels, hire cars and flights — we've got them all. With Expedia, you can shape your Pine Island travel package the way you like it. All you have to do is work out exactly what you need. Once you've made your booking, why not add fun things like activities and tours? The more you bundle, the greater your savings! Expedia features all types of properties, with the most sought after in Pine Island being private holiday homes and bed & breakfasts. With Expedia, you'll always have the freedom and flexibility to personalise your holiday any way you like.
Does Expedia offer Book Now, Pay Later Pine Island holidays?
We sure do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits best during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers the ability to pay in multiple instalments that fit all budgets, so you can have that well-deserved holiday sooner.
  • No-deposit holidays: When you come across an amazing deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Pine Island Expedia holiday?
With a holiday package, you're in control. Whether you're eager to fly to Pine Island in business or coach, simply select from the available airline options. Expedia has access to over 400 partner airlines throughout the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.