The Heights Holidays from £1,423

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Your The Heights Holiday

Book a The Heights holiday package and immerse yourself in the way of life and vibe of this vibrant neighbourhood. With all your travel plans worked out, the only thing you need to worry about here is having the time of your life. Begin your trip to The Heights with a visit to nearby attractions such as Sunset Beach, Crescent Beach and Sylvester Manor. Stop daydreaming and start doing. When it's time to book your holiday to The Heights, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
Hilton New York Times Square

Hilton New York Times Square

4 out of 5
Manhattan
Price was £2,374, price is now £1,423 per person
£1,423
per person
14 Jun - 17 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.6/10 Excellent! (1,902 reviews)
We enjoyed our stay at this Hilton location. The room was very spacious compared to other manhattan hotels. The property is I a great location, close to many attractions and food options. No excessive noise despite being in the heart of the city. The staff was great but especially the first level bag/concierge gentlemen. They were especially friendly and handled our items with care. We were also running late to our train but thanks to one gentleman’s quick service we were able to make it on time.

Reviewed on 13 May 2026

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Price was £3,080, price is now £1,924 per person
£1,924
per person
22 Jul - 25 Jul
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
great time thank you

Reviewed on 12 May 2026

Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was £4,352, price is now £2,739 per person
£2,739
per person
25 Jul - 1 Aug
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (7 reviews)
Courteous and friendly staff

Reviewed on 4 Nov 2025

2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Save 100% on your flight
Price was £4,333, price is now £2,735 per person
£2,735
per person
22 Jun - 25 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
10/10 Exceptional! (1 review)
Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on 19 Mar 2026

Modern 4BR 2.5BA Duplex For NYC

Modern 4BR 2.5BA Duplex For NYC

2 out of 5
The Heights
Price was £2,634, price is now £1,671 per person
£1,671
per person
14 Jun - 17 Jun
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
10/10 Exceptional! (1 review)
nuestra estadia en este lugar fue muy buena! habitaciones comodas, Una casa amplia, No tan lejos de la ciudad, Tienen parking lo cual facilita mucho tu estadia, Sin duda volveremos!!😁

Reviewed on 24 Apr 2026

Top hotels in The Heights

The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is £136 per night from 17 May to 18 May
£136
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (496 reviews)
Great for dogs - huge fenced yard

Reviewed on 11 May 2026

The Bentley Hotel Southampton
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is £295 per night from 27 May to 28 May
£295
27 May - 28 May
includes taxes & fees
8.4/10 Very Good! (647 reviews)
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.

Reviewed on 11 May 2026

Sound View Greenport
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
The price is £328 per night from 7 Jun to 8 Jun
£328
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (613 reviews)
Nice room and view

Reviewed on 15 May 2026

Sag Harbor Inn
See all 4,094 properties in The Heights
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

How much does a The Heights travel package cost?
Perhaps less than you imagined — from a low £1,423, actually! By combining hotels, flights and car rentals into your own customized travel package, your trip to The Heights is just clicks away.
If I'm not able to travel, can I cancel my The Heights travel package?
We understand — sometimes life doesn't go according to plan. If you've booked a The Heights travel package and need to amend or cancel it, we can help. We suggest looking up our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to cancel or change your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to The Heights?
Crafting your own The Heights travel package with Expedia is an easy way to save. We offer more than 550 airlines and 1,000,000 hotel options globally. With such a broad range to pick from, you'll have no worries putting together your next dream escape.
Does Expedia offer Book Now, Pay Later The Heights holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply select the payment plan best suited to your needs during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all budgets, so you can book that well-earned holiday sooner.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in The Heights?
With fascinating attractions such as Sylvester Manor and Crescent Beach in this area, try to find a hotel near either of them. Sunset Beach is another sight that travellers flock to.
What are the top hotels in The Heights?
House On Chase Creek and Shelter Island House are among the most well-known hotels in The Heights. Why not check out the rates and amenities at each and then make a decision?
How far in advance should I book my The Heights holiday?
Smart travellers often reserve their seats as early as possible. You can generally look up international fares on Expedia up to 12 months before your flight. If you're booking last minute, fear not. Bargain prices occasionally appear just weeks before departure.
What does an Expedia The Heights travel package include?
Flights, hotels and rental cars, or any combination of the three — it's up to you! Whether you're venturing to The Heights with the whole family or travelling with your friends, there's a package to match your style and budget. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking a The Heights travel package?
When you book your flights, hotels and car rentals together, you'll enjoy amazing discounts. Whether you're organising an outdoor getaway in a chalet or want to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a The Heights Expedia travel package?
Yes, so take your pick! Expedia has access to more than 550 airlines throughout the world, so you can design your The Heights trip according to your needs and budget.

Popular places to visit

Sunset Beach

Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.

Sunset Beach

* 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.